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I’ve struggled for a large part of life with my desire to do, try and learn a wide variety of things.

Many of the things I’ve tried were totally unrelated to what I’ve previously done and lots of them required starting from scratch. Not to mention the new professions or areas of expertise that take more than two hands to count.

I’ve learned from hard, personal experience that trying to go against your nature is a losing battle. Some people can temporarily win that battle because the rewards for achieving work goals are large and the risk and uncertainty of abandoning ship are unbearably high.

Jack-Of-All-Trades Are Making a Comeback!

It’s unfortunate that nowadays the jack-of-all-trades is looked down upon and the specialist revered—as well as interviewed for soundbites. It’s important for polymaths to not put too much value in how others perceive them and aim for their own long-term happiness instead.

These aren’t the best circumstances for generalists, but it’s also a great time to learn from lots of different disciplines. Having broad knowledge that resembles a liberal arts curriculum is especially useful when it comes to investing and having a latticework of mental models to pull from.

Let the specialists continue with their knitting—which on occasion is interesting to hear about is small doses—but most of the time if a conversation partner keeps going on about the same subject it’s yawn-worthy.

Don’t get me wrong, there are lots of very interesting and happy specialists that should be specialists, which we definitely need in our society.

Growing Up and Feeling Like a Round Peg Surrounded By Square Holes

When I was younger I felt out-of-place since I wanted to do it all, but I felt pressure from family, friends, society, and the media to decide (or settle on) what I wanted to do for a living.

As a teenager, I lacked control and had too many projects going on at one time, most went unfinished (my parent’s front yard and driveway looked like a junkyard since I owned 6 or 7 cars, most weren’t running).

Now when I look back it was clear that I was taking on too much for where I was in my development or didn’t yet possess some basic skills (or have access to YouTube or Google to figure things out).

As I’ve grown I’ve learned to balance and prioritize what’s on my plate more, complete more projects, reach more milestones, and push through challenges (even after losing that initial intense interest).

I ended up graduating college with a degree in Finance & Investments when I was 28 (!!!), I made sure to take some time to travel, explore different types of work, read, think, and experience before biting that bullet.

It also helped that I tore my rotator cuff and broke some bones while working on an organic farm to get me back to school—again.

I didn’t put that degree to work directly and later leveraged my analytical predisposition to land in the corporate world.

“Mo Money Mo Problems” If You Mix Up Ends & Means

And as a former corporate employee that specialized more and more for more and more money, I realized that there’s an abundance of repressed generalists and polymaths out there. Many have chosen to turn their curiosity off or tone it down dramatically (and pursue their passions as hobbies, occasional indulgences or put it off till some unknown future time) to perform at a high level in ever-narrower work niches.

For me going deep into analytics at the enterprise-level at one political organization after another eventually became unbearable.

But some more living had to happen before accepting who/what I am.

Fast-forward 6 years…

Embrace & Love Thyself

I’ve recently fully embraced my need to have a broad set of interests and skills while seeing it as a positive. I’m unabashedly adding more skills to my “toolbox” regularly, while taking on more projects than I should, but I’m also getting more projects done than ever before…

What led me to take the leap and totally embrace being a generalist was:

  • Doing a budget analysis (in a spreadsheet) of my current and future expenses to figure out how I could make it work and for how long
  • The circumstances in my life after my divorce made me much more comfortable with the minimal risks involved
  • Prioritizing my current and long-term happiness over large financial rewards in the present (and pushing the timeline out a bit to hit my financial milestones)
  • Starting to work with my body more and realizing I love working with my hands, being a great dad, investing, writing, working on the computer, reading, cooking, baking, gardening and so much more… And I did not need to pick just one, and that can have it all, but have to juggle a bit and space things out, while giving myself some slack and not feeling guilty if I have to shelf projects

What’s truly blissful for me is regularly trying different things, messing up, and taking on new learning curves (which is love/hate for me). From the other generalists in my life, it seems like that’s a pretty common theme.

“The Best Is The Enemy of The Good”

Being aware of my perfectionism and regularly butting heads with it also helped. My high standards made things intimidating if I couldn’t do something perfectly (or at least “perfectly” from my perspective).

Giving myself the space to mess up and not demand things be perfect relieved lots of pressure that previously left me paralyzed and unable to take the first steps to begin projects.

Trying lots of things and not settling on what seems like the right thing to pursue for the sake of others is actually a statistical advantage, since the more things you try the more likely it is you’ll strike upon something you love doing AND are good at.

I don’t know what I’ll be doing 10 years from now, but I know what I want to focus on for the rest of this month and year. I will gladly renew at the end of the year if it continues to challenge, fulfill, and excite me or readjust if things change.

That’s one of the wonderful perks of being a generalist, having a choice to continue or stop doing something.

Living Below Your Means & Financing The Luxury of Choice

By living below my means, having an awareness of compound interest, and investing the surplus I’ve relieved the pressure to earn lots since my material needs are pretty basic and my expenses are NOT constantly growing, while my assets and investments are constantly growing.

Being in a relatively low-cost situation like this gives me (and you) options and a powerful feeling of being in control, and is much easier for people with average incomes to achieve than making gobs of money (don’t get me wrong, I have some of this in me, but I know my numbers and what I need to retire before turning 45, so even if I don’t end up with massive financial surpluses I’ll be well off, the surplus would just be the “cherry on the top” that provides a larger cushion and some extra luxuries, not a critical milestone needed to achieve financial freedom).

This freedom to explore like a child helped me find myself again—after a long hiatus—and I’m grateful for this luxury and wish others can rekindle some interests and skills that they’ve nearly forgotten about.


Progress: 7 of 9 posts completed (2 left)
Words written (target 750 – 1250): 1,242

Note: This post, which is part of my 30-day procrastination challenge, was one day late. It was one of those more personal posts that some parts were hard to even write down knowing it will be public and for a brief moment considered stopping the challenge. I got over that quick. It was also a bit of a mess since it turned into something different than what was originally intended as I progressed. I’m very happy with the final piece, even though it took a lot longer than normal to edit (so it wouldn’t be total poop on a screen).