Personal Finance (Not Investing) • A different kind of midlife crisis

It’s been about 5 years since I made this post and wanted to circle back with folks. I changed jobs ~3 years ago and my career shifted from a string of Fortune 500 companies to a private mining and extraction company with about $100MM in annual sales and 200 employees. I report to the owner of the business and have fantastic access to all parts of the business including banking, insurance, contract management, sales, and supply chain. This has been a lot of fun.

As to money, the salary is about the same as my previous Fortune 500 role and bonus structure can be better or worse (very nice EBITDA driven bonus vs. legacy of bonus+RSUs) and I was able to write my own contract. I had excellent benefits in my prior companies but less so now. Over the long term this may be an overall better or worse move financially, and it’s difficult to make that call now. As to flexibility, I have the freedom to do the job anywhere in the US and ownership has full faith I’ll continue to execute. This has allowed a greater ability to travel and we’ll likely relocate in the near future.

It’s been very rewarding and the role has provided new learning, flexibility and growth. There are days where the stress and challenge are high, but I can’t see going back to megacorp after this. I also believe there are many companies of similar size out there who need seasoned business professionals that are open to the “intraneurs” to borrow the term from SoAnyway below.

I wanted to give a shout out to folks who provided a lot of very helpful advice back in 2019 on entrepreneurship as I was just starting down this path. Below are the clips of the most help advice, and the guidance which has seemed to apply most to my journey. Thanks to each of you for taking time to write and I hope this is useful to others thinking through their next career move.

...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

There's a saying that "experience is a cruel teacher". But sometimes you need to try things to understand what's going to blow your hair back. Agree completely.

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

Appreciate that Klangfool points this out. When you move from MegaCorp to a small to medium sized business, you are not going to get white glove training and support. It is likely to be very sink or swim, and you need to be a self starter, good with people, and motivated to succeed. Just showing up is not going to cut it.

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.

This has not been my experience either, but you learn a lot when you go through difficult times in a company. Having worked at a megacorp through a Chapter 11 process and working at the struggling company I work for today has taught many important lessons.

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.

Agree with this completely. Don't take on a new challenge without great support at home...thankful to have this.

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.

Good advice. The idea of "safe" is funny actually as the last 2 companies I worked for were acquired shortly after I left and 95% of the legacy workforce was laid off for G&A synergy.

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....

This is the best advice I could have received in the thread. Thank you SoAnyway. The job I have today will be the template I use for future roles, and you helped clarify this in my search and experience.

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*.

Medium sized S-Corps like what you described are more likely to offer flexible terms for people they value....like working 3/4 time as in Thx1138's case. I didn't pick up on this at first but can see this now.

Statistics: Posted by ChowYunPhat — Sat Sep 21, 2024 3:10 am — Replies 61 — Views 8531

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