It’s become quite clear that pursuing solo-entrepreneurship and starting Peak Frameworks has been my overall best career choice.

It’s given me financial freedom, time freedom, and geographical freedom. 

Entrepreneurship is the anchor that allows me to organize the rest of my life. It’s also completely renewed my sense of joy for work and allowed me to pursue music seriously.

Like every path, entrepreneurship is not for everyone. But for the right kind of person with the right kind of tenacity, it is by far the best possible (and most fun) option. 

I’ve run my own company for 6 years now and I think people overestimate how “scary” it can be.

To me, “scary” is living a life that continually undermines your genuine goals and desires. “Scary” is looking back on your life through a lens of bashful shame, with a litany of questions regarding your potential that you can no longer answer.

I believe that most capable employees can start a successful one-person business.

I genuinely believe almost every person I worked with in private equity and investment banking has the intelligence to build something valuable.

If you tackle a problem people already pay for, use a proven business model, and leverage some of your niche competence, you’ll figure it out eventually. Sell high-margin stuff that has consistent demand in an industry you sort of like.

What most people who consider entrepreneurship lack is not the skills or hard work, it’s the courage and self-belief.

In this post, I’m going to discuss a few signs that I think suggest entrepreneurship is right for you:

• Sign #1: Your motivation is much lower than it has been in the past
• Sign #2: You are being under-utilized at work
• Sign #3: Your ideal career path doesn’t seem to exist
• Sign #4: You are constantly thinking of new schemes/side projects

Sign #1: Your motivation is much lower than it has been in the past

The archetype I mourn the most is the former star student who dwindles in a job they neither enjoy nor excel at. That was me!

There is so much untapped potential in this category of person, often trapped behind the bars of misaligned incentives.

And guess what? Aligning your incentives is actually super, super easy if you have meaningful equity and run your own business.

In contrast, I think it’s tricky to be properly motivated if you’re just a salaried employee. Why would you put in 100% effort to make someone else disproportionately rich?

It may be useful to ask yourself:

• Did you used to take pride in your achievements?
  
• Have you ever really cared about something “just because”? Maybe school, sports, a side-hustle, growing a social media account or newsletter?
  
• Do you commonly pursue excellence in other areas of your life, but not necessarily in your job?

If the answer to any of these is yes, I would wager that you simply don’t have a proper vehicle for your career ambition.

I would wager your job is misaligned from your personal goals.

I’ll bring up school and owning a house because I think they’re good examples.

In school, you have 100% equity in your marks. You are the sole beneficiary of your effort (…and maybe your parents, if you count bragging to other parents).

If you work harder, you get better grades and thus it’s generally easier to be motivated.

Owning a house is similar: you become more compelled to improve your surroundings and do the dirty work, as you’ll directly accrue the benefits.

Salaried jobs for the most part are not like this.

Your reward for good work at a job is typically just more work. Maybe some mild recognition or if you’re lucky, a moderate discretionary bonus.

In truth, you’re incentivized to minimize the amount of time spent to meet a minimum threshold quality.

This is a horrible, humiliating incentive system for people who like to excel.

Sign #2: You are being under-utilized at work

Most employees need to generate more profit for their company than whatever their salary is.

That means that there’s value you are generating that you are unable to capture (typically due to your lack of equity).

This under-utilization is even more evident if you feel like you have extra time or energy to give that your employer simply does not want.

If your ideas are being shot down, if you’re being limited for advancement, or if some of your work is being lost to process… you are definitely leaving money on the table.

I think this is particularly true if you have some unique permutation of skills.

For example, I really enjoy writing, making content, and writing little guides.

But there’s virtually no job at a private equity firm that would properly compensate me for how good I am at those things. The only way to be compensated for my odd mosaic of skills is to start a company at that cross-section.

In my opinion, if you are very good at two non-related skills, it’s extremely likely that some facet of your skillset is being underutilized.

We are often not the specific shape that jobs require us to be.

Sign #3: Your ideal path doesn’t seem to exist

This brings us to the observation that rung truest to me – if you have seemingly unique desires, you may need a unique path to realize them.

I find that the people with uncommon outcomes either had an uncommon headstart or are willing to pursue uncommon approaches later in life.

When I was starting Peak Frameworks and Arial Ten, I couldn’t find a single person to reliably “guide” me. I looked pretty hard too.

Most people I talked to thought the finance prep market was completely saturated and couldn’t listen to my dream of becoming a musician without smirking. Now I get to do the smirking.

What I eventually realized is that the Path is the Path because many people can walk it.

The common Paths are designed to comfort a common denominator of ambitions among a varied group of people. But people are way more unique than that.

When I meet people with financial freedom, I see a huge variety of pursuits. You get to see how different people’s underlying ambitions and interests really are.

I know people who travel full time, pursue niche hobbies like competitive video games or surfing, or who want to continue stacking their wealth.

Main point being: if you have a specific unique goal or want an uncommon life setup, you’re not going to find an exact playbook.

Sign #4: You are constantly thinking of new schemes/side projects

The last tell I’ve observed in almost everyone who’s switched to entrepreneurship is the compulsion to investigate new schemes or side projects.

The schemes don’t always have to be profit-oriented or successful. It’s just that weird, unshakable need to investigate and pursue things during your down time.

I was looking back at my time in NYC and I had an… interesting array of failed side projects and curiosities.

I of course dabbled with e-commerce, crypto, and music production. I was already writing janky PDF guides about my recruiting process into private equity and investment banking.

Me and my friends applied for a marijuana store license when Ontario was first privatizing it.

And probably the most hilarious: I first learned how to edit videos in order to clip Simpsons episode highlights for YouTube ad revenue (a strategy which no longer works).

If you just like doing… stuff in your downtime, I think you have the right personality for entrepreneurship.

If you enjoy being productive, learning new things, and being a beginner, I think you have the right mindset.

Conclusion

I don’t want to come off as preachy or braggy. I know starting a company isn’t for everyone.

I know many people who have tried entrepreneurship and hated it. Some people enjoy structure, dislike uncertainty, or simply don’t have that dog in them.

But I know many of my close friends are smart enough and determined enough to figure it out.

I know there’s a mid 20’s version of me out there somewhere looking for precedents just like I was. Some jaded finance guy trying to do the same calculus I did.

And selfishly, I think my life would be a lot better if I had more friends doing lifestyle entrepreneurship.

I need more people to play basketball with at 3pm and go on extended group trips with.