A different kind of midlife crisis

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ChowYunPhat
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A different kind of midlife crisis

Post by ChowYunPhat »

The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
A wise man and his money are friends forever...
RL1013
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Re: A different kind of midlife crisis

Post by RL1013 »

ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
I want to recommend a podcast called Side Hustle School by Chris Guillibeau. He discuss one business idea per day. I suggest you pick up a side hustle and if you like it, develop it into a fill time business.
DarkHelmetII
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Re: A different kind of midlife crisis

Post by DarkHelmetII »

I have made my own side projects, built with my own personal computer and hosted on my own personal cloud workspaces, that are still relevant for my corporate day job. I am effectively killing two birds with one stone. Over the past few years have been amassing collateral that could one day be used to position me for my own gig, but in the immediate term helps me secure higher bonuses etc... through greater success with my employer.
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Re: A different kind of midlife crisis

Post by knightrider »

My 2 cents, is don't do it. You'll get best bang for your buck investing in your mega corp career. Side-hustles are all distractions that yield little and damage your reputation at your mega corp.. It's ok to do some fun hobby kind of projects. But that's all I would suggest doing..
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

RL1013 wrote: Thu Feb 14, 2019 1:09 am I want to recommend a podcast called Side Hustle School by Chris Guillibeau. He discuss one business idea per day. I suggest you pick up a side hustle and if you like it, develop it into a fill time business.
Thanks RL - my bend would be towards changing careers vs. a side hustle. I'm "all in" related to my current role.
DarkHelmetII wrote: Thu Feb 14, 2019 7:47 am I have made my own side projects, built with my own personal computer and hosted on my own personal cloud workspaces, that are still relevant for my corporate day job. I am effectively killing two birds with one stone. Over the past few years have been amassing collateral that could one day be used to position me for my own gig, but in the immediate term helps me secure higher bonuses etc... through greater success with my employer.
Love the post DarkHelment, and Spaceballs for that matter. I pour a great deal of myself into work, to the extent that a side hustle and some hobbies are squeezed out. My focus would be owning or joining a small business and I'm looking for experience from posters who've left Megacorp completely to pursue an entrepreneurial opportunity.
knightrider wrote: Thu Feb 14, 2019 8:49 am My 2 cents, is don't do it. You'll get best bang for your buck investing in your mega corp career. Side-hustles are all distractions that yield little and damage your reputation at your mega corp.. It's ok to do some fun hobby kind of projects. But that's all I would suggest doing..
I'm in agreement Knightrider. Appreciate the reply.
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smitcat
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Re: A different kind of midlife crisis

Post by smitcat »

ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
We worked for large companies for about 25 years.
Along the way we tried and started various small business 's while still working in the corp. world.
We refined what our real interests and goals were and began a larger startup with one of us running that.
About 5 years later we started a second parallel business with the other spouse invoved there and left corp america totally.
"How did you find the opportunity?"
A number of years of casual but detailed research.
"What advice would you give someone seeking such an opportunity?"
One key question - do you really want to be your own boss? This sounds simple but there are many folks who will not thive in an environment where they are the decision maker for all actions.
"Tell us about your evaluation process of the opportunities? "
It evolved over time but became a set of folders , one for each assessed opportunity with the key items we wanted to know about that possible business. Those key items were eventaully posted on a spreadsheet showing which business opportunities had which traits so we could more easily compare them. In our case we ended up with about 25 folders.
"What would you have done differently in your eventual career transition, if anything?"
We would have started this earlier ... at that time we had no mentors , no family was ever self employed, no financial backing, no internet to 'consult' with , no idea of sources for information and assistance.
"Regrets?"
None , other than we could have done this earlier in life, It has been great for us.
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Re: A different kind of midlife crisis

Post by KlangFool »

ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
ChowYunPhat,

Before you start, you need to ask yourself a very simple and important question: why would you want to do this? What is your motivation?

KlangFool
DarkHelmetII
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Re: A different kind of midlife crisis

Post by DarkHelmetII »

ChowYunPhat wrote: Thu Feb 14, 2019 9:01 am
DarkHelmetII wrote: Thu Feb 14, 2019 7:47 am I have made my own side projects, built with my own personal computer and hosted on my own personal cloud workspaces, that are still relevant for my corporate day job. I am effectively killing two birds with one stone. Over the past few years have been amassing collateral that could one day be used to position me for my own gig, but in the immediate term helps me secure higher bonuses etc... through greater success with my employer.
Love the post DarkHelment, and Spaceballs for that matter. I pour a great deal of myself into work, to the extent that a side hustle and some hobbies are squeezed out. My focus would be owning or joining a small business and I'm looking for experience from posters who've left Megacorp completely to pursue an entrepreneurial opportunity.
One other perspective to consider is to take a more entrepreneurial role within your Megacorp or another Megacorp. Over the past 5+ years in my career, I have been slowly drifting closer to sales to where I am now officially part of the sales organization (did not necessarily plan this but is how the cards unfolded). So perhaps an option is to take some of the incremental risk of a more sales or innovation-oriented type role while still having the relative security that goes with a larger organization.
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Re: A different kind of midlife crisis

Post by smitcat »

knightrider wrote: Thu Feb 14, 2019 8:49 am My 2 cents, is don't do it. You'll get best bang for your buck investing in your mega corp career. Side-hustles are all distractions that yield little and damage your reputation at your mega corp.. It's ok to do some fun hobby kind of projects. But that's all I would suggest doing..
This is not the case with us and some of the folks we know. Perhaps you have seen examples that we have not experienced.
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Re: A different kind of midlife crisis

Post by Sandtrap »

Employment to > > > Entrepreneur =

Steady (almost guarantee) Paycheck > > > Nothing

Bills Paid Regularly > > > > Bills not paid

Predictable Monthly Expenses > > > Chaos

Rising Savings Rate > > > Erosion of Savings to Keep New Business Afloat

Standing on Solid Ground > > > Jumping off a cliff into a bottomless abyss

Peace > > > Battle (daily -- adapt, improvise, overcome)

Peace > > > Stress

Sanity > > > :oops:

This is why 99% of new businesses fail.

OTOH

What a ride!!!!!!!

Feeling of success and potential financial rewards. :moneybag :moneybag :sharebeer

If you have what it takes in your bones to be an entrepreneur, either you would have already, or nobody can stop you. Like and artist with art, a musician with music, "you will be driven". :annoyed

And, when you succeed as an entrepreneur, you will feel; more powerful than a locomotive, faster than a speeding bullet, and able to leap tall buildings at a single bound. . . .

*disclaimer: metaphors are comparatively speaking. . .so to speak. . . for illustrative and entertainment purposes only. . . :happy
Last edited by Sandtrap on Thu Feb 14, 2019 10:04 am, edited 2 times in total.
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BuyandHold37
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Re: A different kind of midlife crisis

Post by BuyandHold37 »

ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
I got out of corporate for a couple years and did my own thing. I found that I didn't enjoy having to "sell" my services, and I also had too much time on my hands.

I went back to corporate....the safety and security of a regular predictable paycheck, and of benefits, etc. is less stressful for me personally.
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Re: A different kind of midlife crisis

Post by dgm »

i made the transition. has it been more lucrative? so far better than corp for me, but i think it will end up to be on par with a very successful corporate climber. i have taken significantly more risk but also had much more freedom and lower hours worked.

i have tons of friends for which entrepreneurship did not work and they just went back to corporate after a few yrs. the hit is more ego based but no one has been fatally derailed. generally the outcome distribution is exponential as expected. i know one person who just sold their company for a quarter billion and many many others almost equally smart and hard working who started things which seemed equally promising to me but never found traction. its really tough to be on the majority losing end but statistically most ventures don't end up working out. how terribly will you feel if, a few years down the road you are interviewing for your current position, have significantly depleted savings, and see that your peers have all continued to advance their careers?

having said that it is kind of like learning any skill. you need to try and start failing/succeeding and iterating to get better at it. i knew since graduating i would do my own business and have been preparing and trying things constantly. -- and had a lot of lucky breaks along the way

i'd say just compare the two worst case scenarios and decide which one you'd regret more. trying and failing or not trying and wondering.
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Re: A different kind of midlife crisis

Post by cherijoh »

ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
This is not my personal experience, but that of a friend's husband. He left a big megacorp and decides to become an "entrepreneur". He ended up buying a popular franchise and totally hated it - especially managing low wage employees, having to show up when someone missed their shift, etc. He ended up selling the business fairly quickly even though it was apparently doing okay from the numbers perspective. As I recall, he did a lot of research in the selection process - which I think he may have enjoyed more than actually owning the business. :wink:

His next entreprenurial idea combined two things he loved - flying small aircraft and photography. He has combined two related gigs into a full time job. He has been doing this for the last 10 -15 years and my friend reports that he really loves what he is doing. I'm not sure how successful the business is financially though, since she has a well-paying corporate job and complains about not being able to retire any time soon.

Owning your own business usually means lots of hours getting it up and running. In addition, you can't turn off your brain when you leave for the day, so IMO at least make sure you choose to do something that you love!
Last edited by cherijoh on Thu Feb 14, 2019 9:56 am, edited 1 time in total.
smitcat
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Re: A different kind of midlife crisis

Post by smitcat »

Sandtrap wrote: Thu Feb 14, 2019 9:21 am Employment to > > > Entrepreneur =

Steady (almost guarantee) Paycheck > > > Nothing

Bills Paid Regularly > > > > Bills not paid

Predictable Monthly Expenses > > > Chaos

Rising Savings Rate > > > Erosion of Savings to Keep New Business Afloat

Standing on Solid Ground > > > Jumping off a cliff into a bottomless abyss

Peace > > > Battle (daily -- adapt, improvise, overcome)

Peace > > > Stress

Sanity > > > :oops:

This is why 99% of new businesses fail.

OTOH

What a ride!!!!!!!

Feeling of success and potential financial rewards. :moneybag :moneybag :sharebeer

If you have what it takes in your bones to be an entrepreneur, either you would have already, or nobody can stop you. Like and artist with art, a musician with music, "you will be driven". :annoyed

And, when you succeed as an entrepreneur, you will feel; more powerful than a locomotive, faster than a speeding bullet, and able to leap tall buildings at a single bound. . . .
I believe about 50% of new business's are closed by 5 years out, 50% do reasonably well.
I can only speak for myself about these items in my "C" level job...

"Steady (almost guarantee) Paycheck
Standing on Solid Ground
Peace (battle or stress)
Sanity"

The thought that a corporate job is safe, secure, always provides advancement, has less stress and will always pay the bills was not my experience. Certainly the stress I felt at the larger companies was mostly due to the fact that I could not correct and/or change the issues that threatened both the company and my/our future.
I am sure others may have had a differing experience.
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Re: A different kind of midlife crisis

Post by Sandtrap »

smitcat wrote: Thu Feb 14, 2019 9:54 am
Sandtrap wrote: Thu Feb 14, 2019 9:21 am Employment to > > > Entrepreneur =

Steady (almost guarantee) Paycheck > > > Nothing

Bills Paid Regularly > > > > Bills not paid

Predictable Monthly Expenses > > > Chaos

Rising Savings Rate > > > Erosion of Savings to Keep New Business Afloat

Standing on Solid Ground > > > Jumping off a cliff into a bottomless abyss

Peace > > > Battle (daily -- adapt, improvise, overcome)

Peace > > > Stress

Sanity > > > :oops:

This is why 99% of new businesses fail.

OTOH

What a ride!!!!!!!

Feeling of success and potential financial rewards. :moneybag :moneybag :sharebeer

If you have what it takes in your bones to be an entrepreneur, either you would have already, or nobody can stop you. Like and artist with art, a musician with music, "you will be driven". :annoyed

And, when you succeed as an entrepreneur, you will feel; more powerful than a locomotive, faster than a speeding bullet, and able to leap tall buildings at a single bound. . . .
I believe about 50% of new business's are closed by 5 years out, 50% do reasonably well.
I can only speak for myself about these items in my "C" level job...

"Steady (almost guarantee) Paycheck
Standing on Solid Ground
Peace (battle or stress)
Sanity"

The thought that a corporate job is safe, secure, always provides advancement, has less stress and will always pay the bills was not my experience. Certainly the stress I felt at the larger companies was mostly due to the fact that I could not correct and/or change the issues that threatened both the company and my/our future.
I am sure others may have had a differing experience.
Metaphors are comparatively speaking . . . if not, entertainingly illustrative . . . . .so to speak. . . . :happy
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Re: A different kind of midlife crisis

Post by Sandtrap »

cherijoh wrote: Thu Feb 14, 2019 9:52 am
ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
This is not my personal experience, but that of a friend's husband. He left a big megacorp and decides to become an "entrepreneur". He ended up buying a popular franchise and totally hated it - especially managing low wage employees, having to show up when someone missed their shift, etc. He ended up selling the business fairly quickly even though it was apparently doing okay from the numbers perspective. As I recall, he did a lot of research in the selection process - which I think he may have enjoyed more than actually owning the business. :wink:

His next entreprenurial idea combined two things he loved - flying small aircraft and photography. He has combined two related gigs into a full time job. He has been doing this for the last 10 -15 years and my friend reports that he really loves what he is doing. I'm not sure how successful the business is financially though, since she has a well-paying corporate job and complains about not being able to retire any time soon.

Owning your own business usually means lots of hours getting it up and running. In addition, you can't turn off your brain when you leave for the day, so IMO at least make sure you choose to do something that you love!
Love to hear these business and personal success stories.
thanks for sharing.
j :happy
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Sandtrap
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Re: A different kind of midlife crisis

Post by Sandtrap »

ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
Crouching Tiger,

My Personal Experience:
Educated in Business/Finance/Economics
Worked in Finance
Bored, Underpaid, Felt as if using only .0001% of abilities.
Gave up steady paycheck, vacations, pension, job security (relatively speaking), comfort zone of an employee.
Started a small R/E Development and General Commercial Construction Company (did everything!!!)
Grew > Shrunk > Struggled (repeat) over a period of nearly 40 years.
Sold most of holdings and retired (no pension)
Still love business. It's in my bones.
Would not have done anything differently.

Ip Man
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davidsorensen32
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Re: A different kind of midlife crisis

Post by davidsorensen32 »

Live life like you invest. Stay the course. With Megacorp. Unless you are fortunate to have the following prerequisites:

Personal story. Key goal is to have ZERO distractions while you scratch your entrepreneurial itch. That means:

* Solid home front on autopilot. Meanings kids doing well in school, extras. Kids looked after by in-laws or some such. Spouse fully on board with your decision preferably earning enough to bear all family expenses.

* Must have "F U money" in the bank. Can't stress this enough.

* House paid off, cars paid off, student loans paid off, credit cards paid off - ZERO outstanding loans

* Enough international travel under your belt for a lifetime of memories

* Perfect health - no one in the family has any disability or chronic medical ailment

* Big severance or deferred compensation from MegaCorp that would pay out over the years

* Significant probability of substantial inheritance coming your way in the future

* Solid idea, good partners, strong conviction

* Location where failure is celebrated not penalized e.g. SF Bay Area

* At least $2M+ in angel, series A funding to pay salaries

Remember, in this country only multi-millionaires become billionaires. Play the game only if you have the prerequisite. Not otherwise. For 99.99% of folks sticking to MegaCorp will be the right career decision. And that is the way it should be. Study the posts in this forum. Most 50+ multi-millionaire retirees with secured pensions , paid of homes, paid of college, and happy retirements are either doctors or faceless middle managers in MegaCorps. STAY THE COURSE ! It works.
ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
smitcat
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Re: A different kind of midlife crisis

Post by smitcat »

davidsorensen32 wrote: Thu Feb 14, 2019 10:37 am Live life like you invest. Stay the course. With Megacorp. Unless you are fortunate to have the following prerequisites:

Personal story. Key goal is to have ZERO distractions while you scratch your entrepreneurial itch. That means:

* Solid home front on autopilot. Meanings kids doing well in school, extras. Kids looked after by in-laws or some such. Spouse fully on board with your decision preferably earning enough to bear all family expenses.

* Must have "F U money" in the bank. Can't stress this enough.

* House paid off, cars paid off, student loans paid off, credit cards paid off - ZERO outstanding loans

* Enough international travel under your belt for a lifetime of memories

* Perfect health - no one in the family has any disability or chronic medical ailment

* Big severance or deferred compensation from MegaCorp that would pay out over the years

* Significant probability of substantial inheritance coming your way in the future

* Solid idea, good partners, strong conviction

* Location where failure is celebrated not penalized e.g. SF Bay Area

* At least $2M+ in angel, series A funding to pay salaries

Remember, in this country only multi-millionaires become billionaires. Play the game only if you have the prerequisite. Not otherwise. For 99.99% of folks sticking to MegaCorp will be the right career decision. And that is the way it should be. Study the posts in this forum. Most 50+ multi-millionaire retirees with secured pensions , paid of homes, paid of college, and happy retirements are either doctors or faceless middle managers in MegaCorps. STAY THE COURSE ! It works.
ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
Davidsorensen - I am confused , what was your personal business story?
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Re: A different kind of midlife crisis

Post by MotoTrojan »

knightrider wrote: Thu Feb 14, 2019 8:49 am My 2 cents, is don't do it. You'll get best bang for your buck investing in your mega corp career. Side-hustles are all distractions that yield little and damage your reputation at your mega corp.. It's ok to do some fun hobby kind of projects. But that's all I would suggest doing..
Why not compromise and try to find a role in a fresh startup? New experience, can grow/mentor a young business (and employees) and maybe hit an equity lottery ticket. Also still easy to bounce back unto megacap later on.

I’m early career but went from a 5000-6000 person firm to bring the 5th employee at a business that now has 65 going on 150; lot of fun and financially/career-wise the growth has been significant.
davidsorensen32
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Re: A different kind of midlife crisis

Post by davidsorensen32 »

Smitcat, I was laid off 1+ years ago. Unable to find another megacorp job I worked with a friend to get startup up and running. Along the way I was constantly distracted - I realized that I did not possess most of the attributes I listed in my post. My entrepreneurship daydream became a nightmare. We were not able to find any funding despite many investor pitches. The total cost of missed savings + having to pay lots of costs out of savings for 1 year of unemployment is easily $200,000 in today's $$ - will be $1,000,000+ in 20 years. I bitterly regret my decision to start a startup. I'm back to looking for a megacorp job. Wish me luck.
smitcat wrote: Thu Feb 14, 2019 10:49 am
davidsorensen32 wrote: Thu Feb 14, 2019 10:37 am Live life like you invest. Stay the course. With Megacorp. Unless you are fortunate to have the following prerequisites:

Personal story. Key goal is to have ZERO distractions while you scratch your entrepreneurial itch. That means:

* Solid home front on autopilot. Meanings kids doing well in school, extras. Kids looked after by in-laws or some such. Spouse fully on board with your decision preferably earning enough to bear all family expenses.

* Must have "F U money" in the bank. Can't stress this enough.

* House paid off, cars paid off, student loans paid off, credit cards paid off - ZERO outstanding loans

* Enough international travel under your belt for a lifetime of memories

* Perfect health - no one in the family has any disability or chronic medical ailment

* Big severance or deferred compensation from MegaCorp that would pay out over the years

* Significant probability of substantial inheritance coming your way in the future

* Solid idea, good partners, strong conviction

* Location where failure is celebrated not penalized e.g. SF Bay Area

* At least $2M+ in angel, series A funding to pay salaries

Remember, in this country only multi-millionaires become billionaires. Play the game only if you have the prerequisite. Not otherwise. For 99.99% of folks sticking to MegaCorp will be the right career decision. And that is the way it should be. Study the posts in this forum. Most 50+ multi-millionaire retirees with secured pensions , paid of homes, paid of college, and happy retirements are either doctors or faceless middle managers in MegaCorps. STAY THE COURSE ! It works.
ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
Davidsorensen - I am confused , what was your personal business story?
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Re: A different kind of midlife crisis

Post by smitcat »

davidsorensen32 wrote: Thu Feb 14, 2019 11:59 am Smitcat, I was laid off 1+ years ago. Unable to find another megacorp job I worked with a friend to get startup up and running. Along the way I was constantly distracted - I realized that I did not possess most of the attributes I listed in my post. My entrepreneurship daydream became a nightmare. We were not able to find any funding despite many investor pitches. The total cost of missed savings + having to pay lots of costs out of savings for 1 year of unemployment is easily $200,000 in today's $$ - will be $1,000,000+ in 20 years. I bitterly regret my decision to start a startup. I'm back to looking for a megacorp job. Wish me luck.
smitcat wrote: Thu Feb 14, 2019 10:49 am
davidsorensen32 wrote: Thu Feb 14, 2019 10:37 am Live life like you invest. Stay the course. With Megacorp. Unless you are fortunate to have the following prerequisites:

Personal story. Key goal is to have ZERO distractions while you scratch your entrepreneurial itch. That means:

* Solid home front on autopilot. Meanings kids doing well in school, extras. Kids looked after by in-laws or some such. Spouse fully on board with your decision preferably earning enough to bear all family expenses.

* Must have "F U money" in the bank. Can't stress this enough.

* House paid off, cars paid off, student loans paid off, credit cards paid off - ZERO outstanding loans

* Enough international travel under your belt for a lifetime of memories

* Perfect health - no one in the family has any disability or chronic medical ailment

* Big severance or deferred compensation from MegaCorp that would pay out over the years

* Significant probability of substantial inheritance coming your way in the future

* Solid idea, good partners, strong conviction

* Location where failure is celebrated not penalized e.g. SF Bay Area

* At least $2M+ in angel, series A funding to pay salaries

Remember, in this country only multi-millionaires become billionaires. Play the game only if you have the prerequisite. Not otherwise. For 99.99% of folks sticking to MegaCorp will be the right career decision. And that is the way it should be. Study the posts in this forum. Most 50+ multi-millionaire retirees with secured pensions , paid of homes, paid of college, and happy retirements are either doctors or faceless middle managers in MegaCorps. STAY THE COURSE ! It works.
ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
Davidsorensen - I am confused , what was your personal business story?
Understood - good luck with your future search.
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Re: A different kind of midlife crisis

Post by smitcat »

davidsorensen32 wrote: Thu Feb 14, 2019 10:37 am Live life like you invest. Stay the course. With Megacorp. Unless you are fortunate to have the following prerequisites:

Personal story. Key goal is to have ZERO distractions while you scratch your entrepreneurial itch. That means:

* Solid home front on autopilot. Meanings kids doing well in school, extras. Kids looked after by in-laws or some such. Spouse fully on board with your decision preferably earning enough to bear all family expenses.

* Must have "F U money" in the bank. Can't stress this enough.

* House paid off, cars paid off, student loans paid off, credit cards paid off - ZERO outstanding loans

* Enough international travel under your belt for a lifetime of memories

* Perfect health - no one in the family has any disability or chronic medical ailment

* Big severance or deferred compensation from MegaCorp that would pay out over the years

* Significant probability of substantial inheritance coming your way in the future

* Solid idea, good partners, strong conviction

* Location where failure is celebrated not penalized e.g. SF Bay Area

* At least $2M+ in angel, series A funding to pay salaries

Remember, in this country only multi-millionaires become billionaires. Play the game only if you have the prerequisite. Not otherwise. For 99.99% of folks sticking to MegaCorp will be the right career decision. And that is the way it should be. Study the posts in this forum. Most 50+ multi-millionaire retirees with secured pensions , paid of homes, paid of college, and happy retirements are either doctors or faceless middle managers in MegaCorps. STAY THE COURSE ! It works.
ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
While we never had a goal to be a billionaire (or near that) we did have good time starting and running our business's - we will likely sell them within a short time now.
FWIW - we did not have any of the items listed below...

* Solid home front on autopilot. . Kids looked after by in-laws or some such.

* Must have "F U money" in the bank. Can't stress this enough.

* House paid off, - ZERO outstanding loans

* Enough international travel under your belt for a lifetime of memories

* Perfect health - no one in the family has any disability or chronic medical ailment

* Big severance or deferred compensation from MegaCorp that would pay out over the years

* Significant probability of substantial inheritance coming your way in the future

* Solid idea, good partners,

* Location where failure is celebrated not penalized e.g. SF Bay Area

* At least $2M+ in angel, series A funding to pay salaries
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Re: A different kind of midlife crisis

Post by LadyGeek »

This thread is now in the Personal Finance (Not Investing) forum (career guidance).
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Re: A different kind of midlife crisis

Post by sergeant »

My father had this type of midlife crisis. He asked me my opinion on if he should stay a few more years at megacorp or join a small business owned by my BIL that was very successful but needed some strong management. I told him to stay at his current job until max. retirement pension level was reached.
He didn't follow my advice and joined my Bil"s business. Within 6 months my BIL was my ex-BIL. His company went under and my dad was screwed. A 55 year old in the tech sector is not a hot commodity. I estimate it cost him several million dollars and years of stress. Good luck with whatever you decide to do.
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Re: A different kind of midlife crisis

Post by bhough »

I left megacorp to start my own related business. I had 2 years of living expenses in the bank and had leased an office space, started the website, started a business checking account, lined up what I thought was a large account for the business before I left.

About 18 months later, the business was profitable, but I worked alot, made very little and wasn't able to scale. I self-funded and didn't have any investors, but have recently taken a job with a private firm for income. I could have ridden this out for another few years and maybe scratched a middle income living out of the business, but it didn't look promising. I negotiated with my new employer that I'm going to keep this business on the side (I've got one employee who is working and an answering service for 9-5 hours when I won't be available), but I see this more as a $20,000/year side business than a full time job to support my family.

I would recommend that you stay at megacorp. There is clear data to show that financially, people are better off as employees rather than as entrepreneurs on average (this neglects the .1% that grow billion dollar companies of course) However, if you have 4 million in the bank and no debt and hate your job, that is different. Then the "entrepreneurship" will be for fun, rather than to feed and clothe your kids.

If you absolutely have to scratch the entrepreneurial itch, pay off all of your debt, build up 1 year of business expenses, then do a side business where you can still go to work and give 100% at your job. It takes alot of effort to learn how to run a business and you might find that while you are doing it on the side, you can't sell as well as you thought you could, or your niche isn't as protected as you thought, or that marketing is harder than it looks, or quickbooks is confusing when you start to add in depreciated assets, etc.

Don't jump out of the plane without a parachute. Better yet, don't jump out of the plane. As usual, agree with KlangFool. You should seriously ask yourself why you want to do this.
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Re: A different kind of midlife crisis

Post by vitaflo »

There are steps between being an employee at megacorp and CEO of some startup. You can always start by contracting out your services to other megacorps, which is what I did. Sure I had to leave my employee gig, but I made sure I had a good contract in place elsewhere before doing so. I've been doing that various places for 8 years now.

Along the way you meet a lot of people who do the same thing. Some flame out, go back to being employees. Some get so much work they need to find other people to help them out and boom, you are suddenly running a company with employees. Some work on side projects in the downtime between contracts and end up building something interesting and creating their own startup.

Few years into contracting, I worked at a gig with another contractor who had made an app in his free time. He was making money but wanted to push it farther. We got along well so he asked me if I wanted to buy in for an equity stake to help out, so I did. Worked on that for 4 years, had about 5,000 active users, and about $400k in revenue per year, 20-30% increases YOY. But we were self funded and eventually some VC backed startups entered our space and undercut us to the point where we couldn't compete, so we shut it down. Didn't lose any money on it, cuz we knew enough to see the writing on the wall (gotta know when to fold 'em). We both went back to contracting full time.

I guess what I'm saying is there's more than one road to Dublin. You need to decide what you value. For many it's moving up the corporate ladder at megacorp, cuz they want something "safe" (nothing is truly safe). But for me, megacorps are soul crushing places to be. I'd rather have a root canal than work at a megacorp. I went off on my own because I valued freedom and for me to decide how I want to spend my time, not somebody else. The fact that I get paid a lot more now than I did before is just a nice bonus.
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Re: A different kind of midlife crisis

Post by White Coat Investor »

knightrider wrote: Thu Feb 14, 2019 8:49 am My 2 cents, is don't do it. You'll get best bang for your buck investing in your mega corp career. Side-hustles are all distractions that yield little and damage your reputation at your mega corp.. It's ok to do some fun hobby kind of projects. But that's all I would suggest doing..
They're certainly not all distractions that yield little and damage your reputation. I know of somebody that despite a very high income at a "stable job" grew a side hustle into a far higher income and excellent jobs for four other people. It took a few years but like many side hustles could be done entirely on the side without affecting the main gig much.

I'd say go for it but, in the words of Dave Ramsey, don't jump into the entrepreneurship boat until it's very close to the main job dock income wise. You don't want to end up all wet.
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Re: A different kind of midlife crisis

Post by Sandtrap »

A few from my small circle of senior friends.

1. Started small high tech recycling business. Won contracts for Walmart, Government, State, other agencies for old computer dumping and other high tech equipment. Harvest what could be resold. Melted down for precious metals the rest. And so forth.
Many years later sold the now grown multi-million dollar business for a very substantial sum. Retired.

2. Started a small business making automotive light bulbs with a partner. Grew to supply major automakers. Sold for an extremely substantial sum. Early retired.

3. Started a small health food organic store that sold vitamins and supplements. Grew. Began marketing own supplement line in the now growing health food store. Supplied other stores. Invested in a manufacturing plant for health supplements. Grew that. Sold all to megacorp for an extremely substantial sum. Retired. Has homes across the nation and moves with DW according to the weather.

4. Retired from Megacorp with a large pension. Opened a pizza franchise. Then another. Then another. Then all failed. Still paying off debt.

5. Built up a chain of movie video rental stores (back when they had them). Did well. Sold off the stores. Opened a chain of pizza franchises. All failed. Divorce. Debts. Retired.

6. Retired couple with small pensions. Bought first condo rental on loan. Small income. Then another. Small income. Then another. Small income. Highly leveraged. Barely afloat. Breaking even.
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Re: A different kind of midlife crisis

Post by KlangFool »

OP,

I come from a multi-generations business family. 50% of my family is in one form of business or another. Some people can be successful in business and some people can't. It takes a certain personality type and ability.

In a megacorp, you could be a specialist. You only need to be good in one thing. In a business, you need to be good in several things and you need to partner with folks in the area that you are weak in. You need to do accounting, sell, marketing, product management, and customer management. Any weakness in a single area will doom you.

But, back to the very basic and simple question, why would you want to do this?

A) You will most likely fail.

B) You will work a lot harder and make less or no money for a few years.

C) You will have less freedom. You do not clock out after office hour.

There are exceptions like my older brother. But, we were in our family business since childhood. He ran the family business while in high school. He was a general manager for an MNC. While he was employed at the megacorp, he started 3 companies and sold two of them.

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Re: A different kind of midlife crisis

Post by phxjcc »

OP,

I was a senior manager in IT, making big $'s. In my late 40's I grew tired of the b.s. and took a package and bought a UPS store (MBE at the time).

It was in a great area, the store was top 10% revenue nationwide. People in the area had more money than time. Perfect.

I worked it 10 hours a day, then did inventory, ordering, bookkeeping, and cleaning. Averaged 12 hours. Month end was a 14-16 hour day.

I liked being my own boss and I liked the business but my net was lower than corporate America, so I jumped when I got recruited back into megacorp.

Sold the store (at a profit) to a trust fund baby who was happy to have it.

There is truth to the saying that "you are buying yourself a job".

Get a hobby that makes you happy, play the megacorp game and save your money, then retire.
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Re: A different kind of midlife crisis

Post by SoAnyway »

ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
OP, thanks for starting this thread. You've received good guidance.
FWIW, try not to think in bifurcated "black-white" terms. Your job is not an either/or between Megacorp and Doing your own thing.
Think in terms of the SPECTRUM. At one end lies Megacorp with all of its structure, policies and processes, etc. with all of the plusses and minuses for your financial/mental/emotional well-being. At the other end lies entrepreneurship with all of its excitement of being the boss, making all the decisions, etc. with all of the plusses and minuses for your financial/mental/emotional well-being. There's a whole world in-between. And I'm guessing that most people are somewhere between the two poles as far as their own career satisfaction. Megacorp works great for those who love the stability and structure, and I understand why they'd love it. Entrepreneurship is the only path for those who can't deal with having a boss, and I understand that too.

If one leans hard in either direction, the decision's easy. That's where they should be. I am what I call an "intrapreneur". I don't lean hard either way; rather, I need structure (but not too much). I am (and need to be) creative in problem-solving and am d*mn good at it if I do say so myself when in a context that allows it. Some employment contexts are better for that than others. I've never had use for a "Boss", but I prefer to have a "Gardener" tending to but not micro-managing. Maybe you're the same.

For the first couple decades of my career, I was luckily in organizations that cultivated that "intraneurship" quality. They were past the start-up stage but far from megacorp. I had great managers who insulated me from the bs and body blows they took on my behalf, telling their higher-ups to ignore my somewhat unconventional approaches, sure in the knowledge that the results would speak for themselves. And they did. Sadly, once we succeeded - which of course was the goal - we became a Megacorp with downsides I can't work in. For example, sometime in the 90s I realized that once my employer decided to issue a corporate policy on how to write a corporate policy, it was (way past) time for SoAnyway to find a better way to make a living, hahaha.... ;) So I did. SoAnyway, back to your questions.....

OP, if you're truly at the 90+%ile on the entrepreneur end, others will provide better guidance. If like me, you're at the 70-90%ile range of entrepreneurship, I can help on how to identify those environments you'll thrive in. (They're getting harder and harder to find, but they're there.) If you're more of a Megacorp lifer (0-30% entrepreneurial "itch") stay where you are. Not judging! We're all wired differently....
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

Smitcat - loved these pieces of your post. Taking your time to know yourself and properly research opportunities seems very important. I'm at the stage where my network has expanded to include people who can help evaluate as well as present opportunities. Would love to hear more about what you and your family settled on long-term to the extent you can share. Much appreciated.
smitcat wrote: Thu Feb 14, 2019 9:06 am We refined what our real interests and goals were and began a larger startup with one of us running that.
A number of years of casual but detailed research.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

KlangFool wrote: Thu Feb 14, 2019 9:10 am Before you start, you need to ask yourself a very simple and important question: why would you want to do this? What is your motivation?
Klangfool - it's a fair challenge. I'm at the stage of searching where developing rules or a heuristic for evaluating the next opportunities is next vs. vetting real opportunities. I have a good career in a healthy public megacorp although I know I won't be at the same company in five years for a variety of reasons.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

DarkHelmetII wrote: Thu Feb 14, 2019 9:15 am One other perspective to consider is to take a more entrepreneurial role within your Megacorp or another Megacorp. Over the past 5+ years in my career, I have been slowly drifting closer to sales to where I am now officially part of the sales organization (did not necessarily plan this but is how the cards unfolded). So perhaps an option is to take some of the incremental risk of a more sales or innovation-oriented type role while still having the relative security that goes with a larger organization.
I liked your take DarkHelmet and would suggest my current role has an entrepreneurial and innovation bend to it. Agree there is a spectrum of entrepreneurship. This is worth further thought as it relates to my current situation at MegaCorp.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

BuyandHold37 wrote: Thu Feb 14, 2019 9:30 am I got out of corporate for a couple years and did my own thing. I found that I didn't enjoy having to "sell" my services, and I also had too much time on my hands.

I went back to corporate....the safety and security of a regular predictable paycheck, and of benefits, etc. is less stressful for me personally.
Thanks BuyAndHold. It's a good reminder there's many considerations to make as we consider career changes. Appreciate you sharing your experience.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

Thanks DGM. I liked your question which seems to cut to the heart of the matter for many. This should be sobering if you're making decisions half-cocked. :wink:
dgm wrote: Thu Feb 14, 2019 9:43 am how terribly will you feel if, a few years down the road you are interviewing for your current position, have significantly depleted savings, and see that your peers have all continued to advance their careers?
Seems you also had the "bug" early on.
dgm wrote: Thu Feb 14, 2019 9:43 am i knew since graduating i would do my own business and have been preparing and trying things constantly. -- and had a lot of lucky breaks along the way
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

cherijoh wrote: Thu Feb 14, 2019 9:52 am His next entreprenurial idea combined two things he loved - flying small aircraft and photography. He has combined two related gigs into a full time job. He has been doing this for the last 10 -15 years and my friend reports that he really loves what he is doing. I'm not sure how successful the business is financially though, since she has a well-paying corporate job and complains about not being able to retire any time soon.

Owning your own business usually means lots of hours getting it up and running. In addition, you can't turn off your brain when you leave for the day, so IMO at least make sure you choose to do something that you love!
Thank you Cherijoh. What a cool reboot.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

smitcat wrote: Thu Feb 14, 2019 9:54 am The thought that a corporate job is safe, secure, always provides advancement, has less stress and will always pay the bills was not my experience. Certainly the stress I felt at the larger companies was mostly due to the fact that I could not correct and/or change the issues that threatened both the company and my/our future.
I am sure others may have had a differing experience.
Thank you Smitcat. I've worked at companies on both ends of the stress and financial health spectrums. FWIW, I seemed to learn the most at the distressed companies but they can take some years off your life (firing people, repeat failure, restructurings, etc...). I guess the point is there's no silver bullet when it comes to career and stability.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

Sandtrap wrote: Thu Feb 14, 2019 10:12 am My Personal Experience:
Educated in Business/Finance/Economics
Worked in Finance
Bored, Underpaid, Felt as if using only .0001% of abilities.
Gave up steady paycheck, vacations, pension, job security (relatively speaking), comfort zone of an employee.
Started a small R/E Development and General Commercial Construction Company (did everything!!!)
Grew > Shrunk > Struggled (repeat) over a period of nearly 40 years.
Sold most of holdings and retired (no pension)
Still love business. It's in my bones.
Would not have done anything differently.
Sandtrap, many thanks for the humor (I'm still chuckling) and sharing a bit of your experience. Would love to hear more about your selection of R/E Development & Contracting as a focus. Was this due to relationships or learning from earlier in life? Residential vs. Commercial (or both) projects? Knife edge change or did you gradually make the switch?

Thanks again. And by the way, Chow Yun Fat is a BogleHead or at least subscribes to many of the BH principles. Would encourage you to do a quick read up on him....was interesting to hear his story.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

davidsorensen32 wrote: Thu Feb 14, 2019 10:37 am Live life like you invest. Stay the course. With Megacorp. Unless you are fortunate to have the following prerequisites:
.....
Thank you davidsorensen...that was a good list. I have the prereqs but am not in a hurry. Also wish you best of luck in your career transition.
Last edited by ChowYunPhat on Fri Feb 15, 2019 4:16 am, edited 1 time in total.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

MotoTrojan wrote: Thu Feb 14, 2019 11:28 am Why not compromise and try to find a role in a fresh startup? New experience, can grow/mentor a young business (and employees) and maybe hit an equity lottery ticket. Also still easy to bounce back unto megacap later on.

I’m early career but went from a 5000-6000 person firm to bring the 5th employee at a business that now has 65 going on 150; lot of fun and financially/career-wise the growth has been significant.
Thank you MotoTrojan. This is a possible outcome where the opportunity looks like a leadership role in a small startup. I am evaluating similar such opportunities.
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Re: A different kind of midlife crisis

Post by ChowYunPhat »

bhough wrote: Thu Feb 14, 2019 8:53 pm I would recommend that you stay at megacorp. There is clear data to show that financially, people are better off as employees rather than as entrepreneurs on average (this neglects the .1% that grow billion dollar companies of course) However, if you have 4 million in the bank and no debt and hate your job, that is different. Then the "entrepreneurship" will be for fun, rather than to feed and clothe your kids.

If you absolutely have to scratch the entrepreneurial itch, pay off all of your debt, build up 1 year of business expenses, then do a side business where you can still go to work and give 100% at your job. It takes alot of effort to learn how to run a business and you might find that while you are doing it on the side, you can't sell as well as you thought you could, or your niche isn't as protected as you thought, or that marketing is harder than it looks, or quickbooks is confusing when you start to add in depreciated assets, etc.
Thank BHough. Good info and appreciate you sharing your experience. Nice work navigating the negotiation and balance needed to keep the business with the new employer as well.
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Re: A different kind of midlife crisis

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vitaflo wrote: Thu Feb 14, 2019 10:42 pm I guess what I'm saying is there's more than one road to Dublin. You need to decide what you value. For many it's moving up the corporate ladder at megacorp, cuz they want something "safe" (nothing is truly safe). But for me, megacorps are soul crushing places to be. I'd rather have a root canal than work at a megacorp. I went off on my own because I valued freedom and for me to decide how I want to spend my time, not somebody else. The fact that I get paid a lot more now than I did before is just a nice bonus.
Good stuff vitaflo. Thanks for sharing your story and the guidance as well.
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Re: A different kind of midlife crisis

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White Coat Investor wrote: Thu Feb 14, 2019 11:10 pm They're certainly not all distractions that yield little and damage your reputation. I know of somebody that despite a very high income at a "stable job" grew a side hustle into a far higher income and excellent jobs for four other people. It took a few years but like many side hustles could be done entirely on the side without affecting the main gig much.
Thanks Dr. Dahle and the side hustle story sounds a bit like your story :wink:

BTW, I enjoy your BLOG and Podcast very much.
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Re: A different kind of midlife crisis

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Sandtrap wrote: Thu Feb 14, 2019 11:21 pm A few from my small circle of senior friends.

1. Started small high tech recycling business. Won contracts for Walmart, Government, State, other agencies for old computer dumping and other high tech equipment. Harvest what could be resold. Melted down for precious metals the rest. And so forth.
Many years later sold the now grown multi-million dollar business for a very substantial sum. Retired.

2. Started a small business making automotive light bulbs with a partner. Grew to supply major automakers. Sold for an extremely substantial sum. Early retired.

3. Started a small health food organic store that sold vitamins and supplements. Grew. Began marketing own supplement line in the now growing health food store. Supplied other stores. Invested in a manufacturing plant for health supplements. Grew that. Sold all to megacorp for an extremely substantial sum. Retired. Has homes across the nation and moves with DW according to the weather.

4. Retired from Megacorp with a large pension. Opened a pizza franchise. Then another. Then another. Then all failed. Still paying off debt.

5. Built up a chain of movie video rental stores (back when they had them). Did well. Sold off the stores. Opened a chain of pizza franchises. All failed. Divorce. Debts. Retired.

6. Retired couple with small pensions. Bought first condo rental on loan. Small income. Then another. Small income. Then another. Small income. Highly leveraged. Barely afloat. Breaking even.
Sandtrap, you have quite the interesting circle of friends. Great reminder that there are so many paths one can take to seek professional challenge, be a provider, and frankly do something you're interested in doing.
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Re: A different kind of midlife crisis

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KlangFool wrote: Thu Feb 14, 2019 11:39 pm In a megacorp, you could be a specialist. You only need to be good in one thing. In a business, you need to be good in several things and you need to partner with folks in the area that you are weak in. You need to do accounting, sell, marketing, product management, and customer management. Any weakness in a single area will doom you.
Thanks Klangfool. This seems to apply whether you are on your own, a part of small business team, or leading a small business. A good reminder you definitely have to have a variety of capabilities amongst your leadership regardless of company size.
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Re: A different kind of midlife crisis

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phxjcc wrote: Fri Feb 15, 2019 1:16 am OP,

I was a senior manager in IT, making big $'s. In my late 40's I grew tired of the b.s. and took a package and bought a UPS store (MBE at the time).

It was in a great area, the store was top 10% revenue nationwide. People in the area had more money than time. Perfect.

I worked it 10 hours a day, then did inventory, ordering, bookkeeping, and cleaning. Averaged 12 hours. Month end was a 14-16 hour day.

I liked being my own boss and I liked the business but my net was lower than corporate America, so I jumped when I got recruited back into megacorp.

Sold the store (at a profit) to a trust fund baby who was happy to have it.

There is truth to the saying that "you are buying yourself a job".

Get a hobby that makes you happy, play the megacorp game and save your money, then retire.
Thank phxjcc. Sounds like you scratched the itch. The quote "buying yourself a job" I hadn't heard before and will keep that for later use :)
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Re: A different kind of midlife crisis

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SoAnyway wrote: Fri Feb 15, 2019 2:37 am
ChowYunPhat wrote: Thu Feb 14, 2019 12:22 am The aging process hits everyone a little differently. I'm in a great spot professionally and enjoy my work (megacorp) although there are limited opportunities for advancement in my current role. I'm always looking 1-2 years down the road at the next opportunity and unsure if another megacorp will necessarily be the next landing spot.

I'm interested to hear from those who have worked in a professional environment for a portion of their careers, and then transitioned into an entrepreneurial pursuit of some kind. How did you find the opportunity? What advice would you give someone seeking such an opportunity? Tell us about your evaluation process of the opportunities? What would you have done differently in your eventual career transition, if anything? Regrets?

FWIW, I'm interested in your personal experience vs. a how-to guide. Thanks in advance for sharing.
OP, thanks for starting this thread. You've received good guidance.
FWIW, try not to think in bifurcated "black-white" terms. Your job is not an either/or between Megacorp and Doing your own thing.
Think in terms of the SPECTRUM. At one end lies Megacorp with all of its structure, policies and processes, etc. with all of the plusses and minuses for your financial/mental/emotional well-being. At the other end lies entrepreneurship with all of its excitement of being the boss, making all the decisions, etc. with all of the plusses and minuses for your financial/mental/emotional well-being. There's a whole world in-between. And I'm guessing that most people are somewhere between the two poles as far as their own career satisfaction. Megacorp works great for those who love the stability and structure, and I understand why they'd love it. Entrepreneurship is the only path for those who can't deal with having a boss, and I understand that too.

If one leans hard in either direction, the decision's easy. That's where they should be. I am what I call an "intrapreneur". I don't lean hard either way; rather, I need structure (but not too much). I am (and need to be) creative in problem-solving and am d*mn good at it if I do say so myself when in a context that allows it. Some employment contexts are better for that than others. I've never had use for a "Boss", but I prefer to have a "Gardener" tending to but not micro-managing. Maybe you're the same.

For the first couple decades of my career, I was luckily in organizations that cultivated that "intraneurship" quality. They were past the start-up stage but far from megacorp. I had great managers who insulated me from the bs and body blows they took on my behalf, telling their higher-ups to ignore my somewhat unconventional approaches, sure in the knowledge that the results would speak for themselves. And they did. Sadly, once we succeeded - which of course was the goal - we became a Megacorp with downsides I can't work in. For example, sometime in the 90s I realized that once my employer decided to issue a corporate policy on how to write a corporate policy, it was (way past) time for SoAnyway to find a better way to make a living, hahaha.... ;) So I did. SoAnyway, back to your questions.....

OP, if you're truly at the 90+%ile on the entrepreneur end, others will provide better guidance. If like me, you're at the 70-90%ile range of entrepreneurship, I can help on how to identify those environments you'll thrive in. (They're getting harder and harder to find, but they're there.) If you're more of a Megacorp lifer (0-30% entrepreneurial "itch") stay where you are. Not judging! We're all wired differently....
SoAnyway, very insightful post and thank you so much for taking time to lay this out. Couple of comments:
-"bifurcated" is an awesome word
-Your "gardener" vs. "boss" analogy was fitting. I've little use for a boss as well but my "gardener" is excellent at pruning and watering so to speak. Lots of opportunities to innovate, disrupt, try "a new way and fail", and drive change within my current role at Megacorp.
-I agree with the notion that entrepreneurship can be a spectrum, and I'm also on the 70-90% scale. I believe there are opportunities and environments in my geographic area that fit this well and coincidentally, it's probably where I'll end up. I'm very interested in further thoughts you have on this topic.
-For additional context, my most likely landing spot (besides another megacorp) is a small team at a B2B / capital intensive business serving the larger energy sector in the SW USA.

Quote of the day - "I realized that once my employer decided to issue a corporate policy on how to write a corporate policy, it was (way past) time for SoAnyway to find a better way to make a living"
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Re: A different kind of midlife crisis

Post by thx1138 »

SoAnyway has an excellent summary of a particular kind of "middle way".

I've been the first employee of a start-up company, worked as a civil servant for the DoD for awhile and now am at a medium sized S corp with a lucrative ESOP that's been in business for 30+ years.

At the start up we had six founders plus just me for awhile. One of the founders had the connections and the sales experience. The other five had technical backgrounds but one of them was from a business family and wanted to go that way so took on executive kind of role. While it was an interesting learning experience for all involved it was grueling and lots and lots of cycles are wasted on things that are taken care of for you in a more established organization. Certainly there are mechanisms to outsource many of these things early on but that all comes at a real cost right when money is usually tight. I'm glad to have had the experience of being in that situation but I am also extremely glad I was only in it for about 1.5 years. I was a pretty horrible person to be around during that time - working long hours wears on you and for many people you use up all your "being nice" energy at work leaving you a detestable kind of person to the people who really matter. I had actually wanted to be a seventh founder and had the money to buy in but the team felt they were already founder heavy as it was, I was even less experienced than them by a bit and they were happy to give me a very generous ISO instead. Boy did they make the right call for all of us - I would have hated being "trapped" in that situation. It felt easy to leave in 18 months and walk away from a good fraction of my ISO but I wouldn't have felt comfortable doing that as a founder. They were successful in the end - but it was 13 years to a liquidity event for them! Naively I had always viewed the start up opportunity as something that pays off big or goes out of business in a few years. Actually many of them struggle on for more than a decade before either going out of business or finding a modest liquidity exit.

Being a civil servant was of course an amazing contrast. What it taught me is that even in the most toxic of "MegaCorp" like environments what really matters is the group and team around you. There are highly functioning "bright spots" within some otherwise dysfunctional organizations and usually these are based off of the group knowing how to work around the stupidity and designating a few people willing to be the shields for the creative talent. "Gardeners" to use SoAnyway's term. The issue is that in many of these cases it can be difficult to see much if any financial pay off though you may still have a job you like with great people and the opportunity to work on things you'd never have access to another way.

The S corp I currently work at offers reasonable profit sharing through its ESOP. Being medium sized (about 250 employees now) it is reasonably agile and small enough that you can develop a reputation and get yourself pointed in useful directions. The "gardeners" are adept. I've been here about 15 years and will most likely stay here until early retirement in a decade or so. Already scaled down to 3/4 time. This is pretty decent "middle road" but will never result in a multi-million dollar payoff the way a start up play *might*.

Lastly paying attention to a family member who has worked the "MegaCorp" ladder pretty effectively into high salaries and stock packages I can say that if what you care about is money then the thing to remember is one way or another you need to have a lot of people around typically. A high earner usually "earns" off of the backs of a lot of underlings. Ten worker bees can't subsidize a queen bee particularly well. A few thousand can. The math is simple. If I shave off $1000/head the small team leader has perhaps $10K of revenue to be allocated to them for being a manager. Turn that into thousand heads and now you are at a $1M. Of course the "tax" per head gets smaller the higher up the food chain but the tax goes down slower than the number of reports goes up and so the folks further the top get a much larger fraction of salary increase. So if you want money with reasonable stability there are good paths for that in MegaCorp. And some people genuinely love managing large organizations as they feel they can "think big" and leave the more annoying day to day to others.

There are many paths. It took me a little while to happen upon a good fit for me. I hope you find one that has the right balance for you!
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