Are you an Entrepreneur?


I love being an entrepreneur. I love the freedom of being able to do what I want, when I want, to set my own schedule and set my own course in life. I couldn't imagine myself following any other path (the rare times in life when I did, it usually didn't turn out particularly well.)

Being an entrepreneur is also incredibly hard.

Entrepreneurship often comes with a heavy emotional toll. It's all consuming and takes over your life in ways you can't imagine.

It's a jealous lover that doesn't like to share. 

Here's some straight talk on entrepreneurship, from someone who's been doing it for 19 years. 


When you run a business, it occupies your thoughts all of the time. There's always a problem you're dwelling on, a goal that you're thinking about, an idea that's buzzing around your cranium.

I run a fairly stable company, and I look after my mental wellbeing with daily (OK, almost daily) yoga and meditation. I use productivity tools and apps to keep track of projects and objectives, and try to dump all of my ideas and preoccupations into those tools so they don't occupy my brainspace, but my company is still on my mind most of the time. 

Every entrepreneur I speak to echoes my sentiments. Entrepreneurs are a driven bunch, and because of that drive they're always thinking about their companies.


See the previous point. Most partners find it difficult to relate to or live with someone who is so damn preoccupied. It's a constant struggle to balance your company with the rest of your life (yes, work-life balance is a struggle for almost everyone, but most people who earn a steady paycheck can leave their work at work.

Entrepreneurs don't generally have that luxury - work follows them wherever they go.

And when you're in startup mode, you'll probably work 60 to 80-hour weeks, which is brutal on intimate relationships and hell on your social life. 

it's a crazy rollercoaster.

With my company, I've twice stared bankruptcy right in the face, and had to contemplate losing everything I had worked so hard to create and build. With so much time invested in building a company (years and years of one's life), it's akin to breaking up with a loved one, or the death of someone close to you.

Even now, with revenues approaching $2M/year and a reputation as the #1 company in our industry, I still don't feel any sense of stability or certainty with my business. That said, the highs still outweigh the lows. 


Want to know the 15 apps and tools I use to maximize my productivity? CLICK HERE


Do you have what it takes to be an entrepreneur? I mean, do you really have what it takes?

I'm not talking about the t-shirt-business-on-the-side kind of entrepreneur, I'm talking about making running a business your full-time job and primary income stream.

I'm not saying this to suggest entrepreneurs have some sort of magic ability that the rest of the world lacks, just that entrepreneurship requires a special type of person and a special kind of personality. Not a better person, or a smarter person, just different from the type of person who feels comfortable with a steady paycheck. 

If you want to start a business and make it your life's work, you'd better be able to check off a few of the following traits or you'll find life way too stressful and difficult.

you're comfortable with uncertainty.

If you want to be an entrepreneur, you'd better be OK with uncertainty, because there's precious little of it in the world of entrepreneurship. And with technology developing at breakneck speed, the world in constant flux, and the barrier to entry for entrepreneurship lower than ever before (i.e. lots and lots of competitors), there's less certainty then ever before.

Almost overnight, trends can broadside you like a tsunami; a small change to Google's search algorithm can wipe out 50% of your organic web traffic; a competitor can secure $5M in venture funding and steal all of your clients. Nothing's for granted in the world of entrepreneurship anymore, and you have to be OK with that.  

you're happiest when taking risks.

No business succeeds without taking risks. Indeed, risk-taking is at the very heart of entrepreneurship.

If you want to be an entrepreneur, you'd better be someone who has a history of risk-taking - ideally calculated risk, not just crazy risk-taking for risk-taking's sake - and have benefited from the successful risks and learned from the unsuccessful ones.

you're willing to sacrifice a lot of other things to be successful.

When other people are punching out at 5pm, you'll be in the office or at your laptop putting together yet another spreadsheet, mocking up another wireframe, or figuring out how to fire a toxic employee. Entrepreneurship is not a 9 to 5 calling. 

I've managed to build my company to the point where it runs well without me, and I don't have to log 80-hour weeks anymore, but there was a time when 80-hour workweeks would have felt like a vacation to me. My company still inordinately occupies my waking thoughts, but I've developed a comfort level with it and I'm able to let go more and more.

you can handle the heat - without passing the buck.

As a founder/CEO, the buck stops with you. Always. You can point the finger at your employees, your customers, suppliers, whatever... but ultimately, all of the responsibility falls on your shoulders. You need to realize that when you're the owner, there's no one above you to pass the buck to.

you're comfortable with conflict.

As an entrepreneur, you can't run away from problems. There's no rock you can crawl under, no island you can escape to, where your problems won't find you. You have to get comfortable facing them head-on, or they will bite you in the ass every time. I know this from years of experience (and I'm still working on this one - it's probably my biggest weakness as an entrepreneur).

YOU're driven and probably a little bit unstable.

All of the successful entrepreneurs I know are incredibly driven: driven to succeed, driven to make a difference in the world, driven to make ideas come to life.

Many of them are also a little bit unstable, broken or slightly insane: that drive comes from a place of dissatisfaction with the real world, or with themselves, and they use that drive, and their businesses, to fill the void. At its worst, this can be extremely unhealthy, but at its best, entrepreneurs can find deep fulfilment along with some sort of balance with the rest of their lives.


Despite all of the drawbacks of entrepreneurship, most entrepreneurs I know (I'd go as far as to say almost every entrepreneur I know) wouldn't have it any other way. The price they pay is worth it for the freedom, for the privileged ability to bring ideas to life on a daily basis, and for the ability to make a lasting imprint on the world.

With most entrepreneurs, once they get through the first few crazy startup years and find some sort of stability, they've crossed the Rubicon and there's no turning back. Even if their business fails, they may take a regular job to pay the bills for a while, but meanwhile their wheels are still spinning with the next idea, and it's only a matter of time until they launch their next business. Entrepreneurship becomes the only means to scratch that burning itch, an itch that always needs scratching.


Are you looking to start a business? Are you an entrepreneur already? I'd love to hear your thoughts on this post in the comments below!


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