Transitioning to independent pursuits, struggling with identity/structure

[David Berthiaume]

Hi everyone,

I’m 45, married, with a 3-year-old. My wife has an opportunity for a postdoc in Barcelona (~58k euro salary), and we’re seriously considering relocating from the greater Boston area. I currently have about $3.3M in savings/investments, no debt, relatively low expenses, renting a small house, and I’m generally not a big spender. A wealth manager currently handles my finances/investing.

Most of these savings came from a tech/software startup I co-founded and later sold. I also recently finished a graduate degree at Harvard. About 6 months ago, I left my role as a Principal AI Engineer/Data Scientist at a large company to pursue independent work: working on an open problem in graph theory (Hadwiger's Conjecture) with some strategic guidance from a professor at MIT, some solopreneur work, and eventually selective consulting in AI/geospatial/remote sensing.

A big realization for me recently is that I have a very “spiky” / 2e cognitive profile, unfortunately. I perform well in highly aligned technical/research environments, but *REALLY* struggle in chaotic, meeting-heavy, management-oriented/social, ambiguous roles. I’m now trying to structure my life much more intentionally around that reality rather than forcing myself into environments that are ultimately a poor fit, where I might struggle/fail, and where I'm unhappy and feel I cannot contribute to the world in a meaningful way intellectually.

Financially, we're relatively okay, especially with the lower cost of living in Spain, but I'm not quite where I want to be yet. Assuming I work hard on these pursuits over the next ~20? years and learn what I need to (especially what I learned from my first startup!), I expect to achieve a meaningful income over time. However, I’m still adjusting psychologically to stepping away from a traditional career path and into a much more self-directed one.

I’d love to hear from others who have gone through something similar:

• transitioning away from high-income traditional work (~600k total yearly income) into more independent/intellectual/creative pursuits with less stable income
• balancing meaningful work with financial independence
• deciding when to do consulting and how many hours/week
• managing the psychological side of no longer having a traditional “job”. This has been a TOUGH one for me.

I’d especially appreciate practical advice from people who have already navigated a similar transition!

Thanks!
~David

 

[COcheesehead]

I went from a very structured corporate world into a world of little structure when I started my business from dirt.
I knew all along though that I was better dealing with ambiguity rather than a defined path.
My first year in business I paid myself $32,000, a far cry from making six figures. Over time though my income grew closer to $400,000 and stayed there until I retired. I enjoyed life more though my responsibilities were greater.
You know yourself better than anyone and you probably know the answer to what path is right for you. You just need to step across the line you fear. It’s very liberating.

 

[Koolau]

Sorry but I've always been more of a "sure thing" kinda guy. Once I got a j*b at my Megacorp, I got used to the money and security.

I got my "strokes" by teaching in my field at the local university.

Sorry, but I'm not certain I know what you actually plan to "do" in Spain while your DW fulfills her dream j*b.

 

[target2019]

I went from steady consulting paychecks to virtually nothing in the mid-90's as the mega-corp fell apart.

With two young children, and spouse back to work (healthcare insurance, but lowish pay) I decided to focus on the children, and their growing list of school and extracurricular activities. I have not regretted that at all. Eventually consulting in a different field came back as the kids aged.

With consulting I had better experiences with tasks and projects that were well-defined.

The consulting approach always fit me well, as I was never really that good following direction from others. Lol, that started in grade school.

 

[RetiredHappy]

We both went from high paying megacorp senior execs to starting our own company. We ran it for 8 years before selling it and retiring. Even when we started our own company, we were very structured and process driven. We went from making three-quarter million dollars a year to paying ourselves $6K a year and losing a couple of hundred thousand dollars for the first couple of years before becoming profitable. I cannot see running a business that is unstructured.

 

[tulak]

A few questions to ponder:

1. What will you do in Barcelona?
2. How long will you be there?
3. What are your yearly expenses? Will you wife's 58k euro salary cover this?

From a financial standpoint, at 3.3M, I would probably do it, assuming you don't need to pull more than 66k/USD a year from the portfolio (2% WR). At that rate, you'll still get significant growth, which will help you get to your number, and the experience of living in Barcelona (Europe) would be fun.

I'd invest some time figuring out if, "A wealth manager currently handles my finances/investing," is worth it in your case. You could be better off handling your investments on your own.

Sounds like a great opportunity!

 

[hesperus]

Hi everyone,

I’m 45, married, with a 3-year-old. My wife has an opportunity for a postdoc in Barcelona (~58k euro salary), and we’re seriously considering relocating from the greater Boston area. I currently have about $3.3M in savings/investments, no debt, relatively low expenses, renting a small house, and I’m generally not a big spender. A wealth manager currently handles my finances/investing.

Most of these savings came from a tech/software startup I co-founded and later sold. I also recently finished a graduate degree at Harvard. About 6 months ago, I left my role as a Principal AI Engineer/Data Scientist at a large company to pursue independent work: working on an open problem in graph theory (Hadwiger's Conjecture) with some strategic guidance from a professor at MIT, some solopreneur work, and eventually selective consulting in AI/geospatial/remote sensing.

A big realization for me recently is that I have a very “spiky” / 2e cognitive profile, unfortunately. I perform well in highly aligned technical/research environments, but *REALLY* struggle in chaotic, meeting-heavy, management-oriented/social, ambiguous roles. I’m now trying to structure my life much more intentionally around that reality rather than forcing myself into environments that are ultimately a poor fit, where I might struggle/fail, and where I'm unhappy and feel I cannot contribute to the world in a meaningful way intellectually.

Financially, we're relatively okay, especially with the lower cost of living in Spain, but I'm not quite where I want to be yet. Assuming I work hard on these pursuits over the next ~20? years and learn what I need to (especially what I learned from my first startup!), I expect to achieve a meaningful income over time. However, I’m still adjusting psychologically to stepping away from a traditional career path and into a much more self-directed one.

I’d love to hear from others who have gone through something similar:

• transitioning away from high-income traditional work (~600k total yearly income) into more independent/intellectual/creative pursuits with less stable income
• balancing meaningful work with financial independence
• deciding when to do consulting and how many hours/week
• managing the psychological side of no longer having a traditional “job”. This has been a TOUGH one for me.

I’d especially appreciate practical advice from people who have already navigated a similar transition!

Thanks!
~David

Relocating to Barcelona sounds like an incredible opportunity for your family. Adjusting to a self-directed path after a high-level tech career is definitely a major psychological shift. Take it one day at a time—finding that new structure takes patience.

 

[socca]

transitioning away from high-income traditional work (~600k total yearly income) into more independent/intellectual/creative pursuits with less stable income

In 2007 I transitioned away from a traditional engineering job to (1) a combination of independent/intellectual/creative pursuits generating (almost) no income and (2) running a family business (not in my area of specialization or interest) generating modest income.

balancing meaningful work with financial independence

In my first full year of self-employment (2008), my federal taxable income was $22k, my federal tax-exempt income was $44k, and my federal tax liability was a whopping $1.5k. As the family business prospered over the following years my taxable income increased, but only to the “comfortable middle class” level. With no mouths to feed except my own (didn’t even have a pet) and the proven ability to squeeze a nickel until the buffalo screams, I was happy as a clam. I thrive in an environment where there’s not some jerk in a corner office telling me what to do and defining what constitutes success.

deciding when to do consulting and how many hours/week

I invested as much time and energy in the family business as was necessary for the company to run like a well-oiled money-making machine. Being responsible means “doing whatever it takes”, so I never really had to “decide” how much time & energy to commit.

managing the psychological side of no longer having a traditional “job”. This has been a TOUGH one for me.

Jumping off the corporate hamster wheel was one of the best things I ever did for my mental health. I still had responsibilities and a title but much more freedom in deciding how and when stuff would get done.

 

[David Berthiaume]

Thanks for the responses, everyone! Some answers to the questions above:

"Sorry, but I'm not certain I know what you actually plan to "do" in Spain while your DW fulfills her dream j*b." What will you do in Barcelona? How long will you be there?

If my wife starts a postdoc in Barcelona, I will continue doing what I'm doing. Attempt to finish the proof and computational pipeline for Hadwiger's Conjecture. This is a major undertaking (> 150-200 page framework/proof) and has a huge upside if successful. This is right up there with Fermat's last theorem and the Poincaré conjecture. Continue to build deep geospatial/remote sensing + AI SaaS products, apps, and continue working on indie games (my passion!). Really lean into learning about business and marketing, take classes, and read as many books on the subject as I can. Learn from any mistakes I made with my first startup. I don't know if this is a pipe dream, honestly, but I was successful before here - an 8-figure sale of my startup, so I feel it is worth a shot to do this solo. I just met with my wealth manager, and he said we are all set. Even over the next ~25 years, as I work on this, I make 0 income from these efforts; we are likely perfectly fine. Of course, I don't plan on this, but as an extremely conservative floor, this is comforting. We would be in Barcelona for at least several years and maybe permanently, depending on how well it goes.

I picture these as 2 curves.
Curve 1: I stay on a steady corporate salary, flat line. (Assuming I can get a job in this market!) . More certain.
Curve 2: pursue the solopreneur route. Extremely low salary at the beginning, then the expected value rises over time as I build and learn, with much higher potential upside, but far more uncertainty. I have dozens of ideas here.

3. What are your yearly expenses? Will your wife's 58k euro salary cover this?
58k euros/yr in Barcelona is well above average. Given that we are minimalistic, this should cover most, if not all, of our expenses there. We would almost certainly be drawing at most 1% from my savings each year, and more likely actually contributing.

I thought about this more, and my overall mission statement. I really want to make an intellectual contribution to the world, and I feel that I should pursue this. This is my shot vs sitting through endless meetings and buying a big house + lots of stuff. That doesn't feel like my path at all.

 

[Love This Community]

Not everyone has big dreams and a very few take chances to pursue those dreams for various reasons. You are passionate about your pursuits, have a good grounding with finances, and more importantly, thinking about contributing to the world. If I were in your shoes, I'd just go ahead and live the dream. All the very best!

 

[COcheesehead]

Not everyone has big dreams and a very few take chances to pursue those dreams for various reasons. You are passionate about your pursuits, have a good grounding with finances, and more importantly, thinking about contributing to the world. If I were in your shoes, I'd just go ahead and live the dream. All the very best!

+1
Someone once said men fail not because they take too many chances, but rather too few.

 

[tulak]

Considering you have enough money, you can choose any path.

Enjoy Barcelona!

 

[NomDeER]

What are your wife's thoughts on all of this?

A big realization for me recently is that I have a very “spiky” / 2e cognitive profile, unfortunately. I perform well in highly aligned technical/research environments, but *REALLY* struggle in chaotic, meeting-heavy, management-oriented/social, ambiguous roles. I’m now trying to structure my life much more intentionally around that reality rather than forcing myself into environments that are ultimately a poor fit, where I might struggle/fail, and where I'm unhappy and feel I cannot contribute to the world in a meaningful way intellectually.

I am somewhat similar 2e. I ended up moving away from higher paying/earning potential jobs that required a lot of meetings, were chaotic, required a lot of social interaction, and often did not feel meaningful. (But, what I had been doing was what so many people thought that I was supposed to want and were jobs that others would kill for.) I transitioned to research-heavy jobs that I thought were more interesting, meaningful, and rewarding. Although I did a lot of mentoring, I avoided management. However, it was still fairly traditional work with decent pay.

I have a harder time being productive and efficient when I don't have clear assignments and deadlines. I need structure. (Plus, I would not do well with some of the more administrative and mundane tasks of owning and managing a business.) This is not uncommon for 2es. Do you think you are the same, and do you have a way to ensure that these things are not problems?

FWIW, I also don't buy a lot of expensive "stuff" and I live below my means. I thought that I was making career decisions that were not going to be very financially rewarding, and I even took a couple of no-pay sabbaticals, but I ended up doing fine financially and was able to ER. I was stressed at times, but I did not have your amount of savings and investments. Doing the math and carefully understanding your financial situation can help you and your wife realize that what you are thinking about doing is going to be fine financially.

 

[Diogenes]

If my wife starts a postdoc in Barcelona, I will continue doing what I'm doing. Attempt to finish the proof and computational pipeline for Hadwiger's Conjecture. This is a major undertaking (> 150-200 page framework/proof) and has a huge upside if successful. This is right up there with Fermat's last theorem and the Poincaré conjecture. ...

I'm not familiar with Hadwiger's Conjecture, but have elementary appreciation for the 4-color problem and of course for Fermat and Poincare. If you can tackle something like that, even as a proof limited to a special case, that's Fields Medal material right there. Worry about what to do with one's life, whether to work or not, retirement and so on... become, pardon the pun, academic.

Are you doing this for your PhD, or have you already completed that? Definitely finish your PhD, if you haven't already, because that is the segue into so many formal research positions. You shouldn't be thinking in terms of "career" for W2/1099 or your 401K and so on. That's nugatory stuff for folks whose main contribution to Mankind is just being a decent person and maybe making some widgets on the assembly line. If you're as talented as you say, your main focus should be on how you're going to advance the frontiers of human knowledge... and not whether you'll be getting ACA subsidies, or be able to fly business-class on vacation.

 

[livingalmostlarge]

Do it. You won't regret. If you don't love what you do then you'll just fail. sounds like you really love it so do it. The rest is all noise and will work out. If i sound like I'm just saying things i'm not. BTDT 2x for us. We seem to reinvent ourselves as we see fit.

DH is currently debating also leaving corporate because he hates it. he just needs to hire his replacement. Then we'll see. He says he'll be a professor, we'll see. I think that some of it will be figuring it out. And some of it will come from watching our kids launch.

but either way he's just sitting there deciding what to do.

 

[gauss]

Hi everyone,

I’m 45, married, with a 3-year-old. My wife has an opportunity for a postdoc in Barcelona (~58k euro salary), and we’re seriously considering relocating from the greater Boston area. I currently have about $3.3M in savings/investments, no debt, relatively low expenses, renting a small house, and I’m generally not a big spender. A wealth manager currently handles my finances/investing.

Most of these savings came from a tech/software startup I co-founded and later sold. I also recently finished a graduate degree at Harvard. About 6 months ago, I left my role as a Principal AI Engineer/Data Scientist at a large company to pursue independent work: working on an open problem in graph theory (Hadwiger's Conjecture) with some strategic guidance from a professor at MIT, some solopreneur work, and eventually selective consulting in AI/geospatial/remote sensing.

A big realization for me recently is that I have a very “spiky” / 2e cognitive profile, unfortunately. I perform well in highly aligned technical/research environments, but *REALLY* struggle in chaotic, meeting-heavy, management-oriented/social, ambiguous roles. I’m now trying to structure my life much more intentionally around that reality rather than forcing myself into environments that are ultimately a poor fit, where I might struggle/fail, and where I'm unhappy and feel I cannot contribute to the world in a meaningful way intellectually.

Financially, we're relatively okay, especially with the lower cost of living in Spain, but I'm not quite where I want to be yet. Assuming I work hard on these pursuits over the next ~20? years and learn what I need to (especially what I learned from my first startup!), I expect to achieve a meaningful income over time. However, I’m still adjusting psychologically to stepping away from a traditional career path and into a much more self-directed one.

I’d love to hear from others who have gone through something similar:

• transitioning away from high-income traditional work (~600k total yearly income) into more independent/intellectual/creative pursuits with less stable income
• balancing meaningful work with financial independence
• deciding when to do consulting and how many hours/week
• managing the psychological side of no longer having a traditional “job”. This has been a TOUGH one for me.

I’d especially appreciate practical advice from people who have already navigated a similar transition!

Thanks!
~David

If you don't need the income, volunteer opportunities are great for finding purpose and easier to establish alignment to your individual personality than job jumping IMHO. I found two (or rather they found me) since ER'ing ~12 years ago in my upper 40's.

The best volunteer opportunities from this perspective are ones with natural time cycles built in (ie annual).
That way you have an "out" on a regular basis as opposed to "owning" the position until you can find a replacement for the position.

It is also a good idea to view volunteer opportunities through a lens as primarily "blue collar" vs "white collar". This need not align with what you did professionally.


-gauss

 

[Markola]

One could challenge oneself to master Catalan.

 

[David Berthiaume]

'One could challenge oneself to master Catalan.' - yes, this WILL be a challenge!

 

[kgtest]

I find purpose in community. You may find it somewhere else. By me pursuing that purpose, my life has been really fulfilling and personally rewarding beyond what my working career is and will provide for me...personally.

I never had work as my singular identity, but certainly learned and become a skilled and trusted expert in my profession.

I never liked it when I was in a new social setting that was led with "Oh, so what do you do for work/living??"

I prefer "What are your three favorite hobbies?" If there is no answer to that...eeek

 

[timo007]

We moved from the United States to France in 2025. Salary went from six figures to less than $10k teaching at the local business school. We are now planning a move to another city in France that will have more job opportunities. I started a website focused on helping expats move to France and do some 1-2-1 consultations, but it was never going to be a salary, just a hobby.

There is a lot of opportunity in AI in Europe. I work in corporate finance, which is a bit less in demand...

 

[FD1000]

Let’s get realistic and down to earth.
What percentage of people have $3.3M at any age? Around 3–3.5%.
We could stop right there.
But let’s keep going, because you still have plenty of time and plenty of choices available to you.
You’re the only person who can make this “complicated” decision.

---

I was always very clear, even as a teenager, about what I wanted to accomplish.
I started as a programmer analyst/developer. Later, I became a team leader and quickly realized that management often involved politics, wasted time, and people justifying their existence, so I chose to stay technical.
From that point on, I became a chameleon.
I did what management asked. If I got busy, no problem. If assignments slowed down, no problem.
In my last few long-term jobs, I convinced my managers that meetings were usually a waste of my time and that I’d be far more productive skipping them. Honestly, those were the best years I ever had working in corporate America.

---

No, I never wanted to own a business.
But there was one thing I never compromised on: I refused to work more than 45 hours a week unless it was truly urgent. That worked well in 90%+ of my jobs.
I knew that if I kept working steadily, improved my skills, and saved consistently every month, I would eventually have enough money.
That mindset allowed me to maintain a great work-life balance, be involved in my kids’ activities, and travel the world.
I also understood the statistics around new businesses; most fail. And even when they succeed, the extra hours and sacrifices are usually enormous.

What do I really think about managers, especially upper management?
The quickest way to improve a company’s processes and profitability is to lay off 50% of the managers.
You just need to figure out which 50% to get rid of.
So much for political correctness and fairness.

Everything I’ve done since I was a teenager has been based on common sense, analyzing situations from every angle, and choosing the best approach by weighing all the variables logically without letting emotions drive the decision.
Once I found a process that consistently worked well, I stuck with it for decades.

Lastly, I always told my kids: don’t be spoiled, don’t be lazy, and always do your best. They took that seriously; otherwise my DW and I would have been all over them.

Good luck.

 

[NomDeER]

If you don't need the income, volunteer opportunities are great for finding purpose and easier to establish alignment to your individual personality than job jumping IMHO. I found two (or rather they found me) since ER'ing ~12 years ago in my upper 40's.

ITA. I do volunteer work in ER. But, you don't have to wait until ER. I took a couple of sabbaticals during my career - including in another country - and did volunteer work.

It's great when you can lend your skills and experience to those who really could benefit from it.

For some people, it also can be away to explore new career paths and also help others.

 

[mesnuc]

Much respect to anyone who seeks purpose in what they do. Purpose looks very different for all of us but I like the intellectual and community pursuits. I'm 48, retired military and currently teach brazilian jiu jitsu at a law enforcement academy. Currently working on the right balance of teaching via information processing theory and ecological learning theory in order to give students the competency of a set that can reduce injuries/death for both officers and subjects in a short timeframe while reducing injuries. My pursuits are pretty much lightweight as far as intellectual pursuits go, but it keeps my brain engaged, gives me a sense of purpose and keeps me physically active.

Since your wealth manager says that financially you're set, I say stay away from a job and continue your pursuit of proving the Hadwiger Conjecture.

 

[HI Bill]

The quickest way to improve a company’s processes and profitability is to lay off 50% of the managers.
You just need to figure out which 50% to get rid of.

This! I once worked under a VP. He revised my forecasts of my projects' profits in December so that it would look like the projects were going to make an outsized profit, and enabled him to get an outsized bonus. Come January, the forecasts were corrected. Come March, the VP was gone.

 

[YellowSubmarine]

Hadwiger's Conjecture...something to ponder. What are the ramifications of such a theorem? I watched a quick video on the topic, over my head as it sounded like a flip/enhancement on the binary code...impression only.
Good luck with your endeavors. After 8 years of employment, I started my own company and worked for 29 years. Plenty of challenges, no regrets; and my wife was supportive.