9 Thoughts On Entrepreneurship (After Five Years Of Owning A Business)

_{[Read time: 5 minutes]}

Your opinions can change.

Your perspective can change.

Your beliefs can change.

It’s called learning.

I’ve learned so much since leaping from employee to entrepreneur in 2019.

Next month will mark five years since I started running a business full-time. While I’ve stressed that years are not the best indicator of experience, I consider five years an important marker for assessing (deeply) and evolving.

If you’re behind me in your business journey, use these thoughts as navigation beacons to keep going (and do better than I have).

If you’re ahead of me, use these thoughts as a reminder of how you once felt (or still feel today), and take a moment to assess your path.

Regardless of where you are, this is your reminder that reflection is a catalyst for progress.

Because if you’re an entrepreneur like me, progress is happiness.

#1 — I used to think the goal was to win, but now I realize the goal is to keep playing.

Terms like best, champion, or #1 belong to competitive, finite games.

Entrepreneurship is an infinite game. It's fulfilling, elegant, and demanding. But it can be played forever.

The goal is sustainability, not ability.

I firmly believe Michael Jordan would trade in every championship ring and award to play the game (at the highest level) forever.

#2 — The 5 stages of entrepreneurship are accurate (at least, I can attest to the first 4)

I was aware that every single entrepreneur will experience the 5 stages below. Even armed with this awareness, I still fell into the trap of each.

• Uninformed optimism → super excited but totally ignorant of reality

• Informed pessimism → realize it’s not all that simple

• Valley of dispair → convinced nothing works (or will ever work)

(here is where most pivot, crash, or give up)

• Informed optimism → reality is clearer, and so is the path to the upside

• Proof of achievement → it’s happening (profitably and consistently)

This game may be beautiful, but it is mentally taxing. One day is fantastic. The next, you’re questioning everything.

Keep going.

Here’s my favorite quote on the topic:

“Entrepreneurship is a bumpy road that ends smooth.” (Daniel Priestley)

(speaking of ending smooth…)

#3 — Entrepreneurship has no defined success metric; it's about where you choose to stop.

If you want to build a lifestyle business around you, you can stop there.

If you want to build a massive, multi-dimensional, and sellable business.

Or something in between.

It’s your choice.

#4 — Having entrepreneur-like qualities is very different than being an entrepreneur.

One earns an income; the other generates revenue.

Big difference.

But don’t take that as a discount to employees with entrepreneur-like qualities. If I were to go back, that’s exactly who I would hire.

If you're fortunate to lead a team of them (or even one), consider yourself super lucky — because it’s an asymmetric bet. They have the company's protection on the downside and the ambition to solve a sticky problem with uncapped upside (all while being relentless in the pursuit).

Give them autonomy, resources, and projects to explore without a roadmap, and they will make you look good.

#5 — Entrepreneurs are money-focused and not afraid to admit it, but that doesn’t make them greedy.

“Profits, revenue, margin, scale, and growth” are terms of endearment.

Despite this, entrepreneurs see money differently. It’s a tool that drives them toward a feeling. And it’s “that” feeling they keep searching for.

#6 — Forced participation is the enemy of entrepreneurship.

Force entrepreneurs to do something they don’t want, and they will rebel. Make it their idea, and they will do it better than anyone else.

I remember how I hated some classes in grad school because they were graded based on participation. I seriously loathed them — not because I was nervous about speaking (I actually love speaking and sharing insights)…but because they rewarded surface-level statements.

I cared for real insight, not progress-less words.

This is why I’ve learned that the highest-valued aspect is autonomy.

#7 — Entrepreneurship is filled with contradiction and irony because persistence is the most common trait among the highest achievers, yet most started as quitters.

Quitting is not a bad thing.

If you do it with clarity and awareness, it’s a strategy.

(along the same lines as quitting…)

#8 — If you want to really understand an entrepreneur, don’t ask them ‘what they do’ or ‘how they do it’ — ask ‘how they started.’

My definition of entrepreneurship is broader than most → if your profession is owning a business (whether you operate it or not), you’re an entrepreneur.

That means a small business, big business, freelancer, consultant, coach, start-up founder, bootstrapper, or even solopreneur.

That said, these subsets are a snapshot of the current moment. I have found that the best way to understand an entrepreneur is by how they started.

There are thousands of paths to choose from, but there is only one starting point. Here are four types:

1. The Leaper → a former employee who quit (dropped everything) to start a business from scratch

2. The Transitioner → a former employee who eventually quit once the business showed some potential

3. The Part-timer → the employee who has a side hustle business but wants to keep their job

4. The Original → the one who never had to quit because they were an entrepreneur from the start

I’m a leaper. By the way, there is no wrong door to enter.

#9 — If the entrepreneur had a mascot, it would be the duck.

Methodical and confident above the water, with feet moving chaotically below and always on the hunt for 'bread.'’

Quack. 🦆

I’m grateful you took a few minutes to read this post. I know how valuable your time is, so thank you.

See you next week.

Peter

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If you missed last week’s post

Last week, I wrote:

When The 80/20 Rule Goes Wrong

It’s about how creative and intellectual domains (e.g., business) should consider the impacts of Price’s Law, not relying on the 80/20 rule.

Read why Price’s Law impacts even the smallest companies (and teams).

One final link worth clicking

I mentioned my favorite quote above in #2 from Daniel Priestley.

Here is an incredible deep dive (with Daniel and Ali Abdaal) into building a business.

Hey, if you’re new here

I’m Peter, a former Harvard strategist turned entrepreneur — I help businesses and organizations make the strategic decisions that move the needle.

Here are 2 ways I can help you:

1 — Want to become a better business thinker (or build a team of thinkers)? Book a free 20-minute call with me to learn about how you can channel your mental firepower into your unfair business advantage.

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