Full Disclosure: 12 Reasons You Probably Shouldn’t Be An Entrepreneur (The story no one tells)

Full Disclosure: 12 Reasons You Probably Shouldn’t Be An Entrepreneur (The story no one tells)


“Don’t compare your inside to someone else’s outside.” – Unknown

In Pursuit of the Honest Entrepreneur…

A couple months ago I was wandering around the streets of Mykonos, Greece and came across a little scarf shop. I peeked inside and saw this woman working away. She was so focused on her weaving that at first she didn’t even notice the sunburned foreigner in the doorway staring and smiling.

The pieces she was producing were gorgeous – they covered the walls making the whole shop look like an endless painted canvas.

But what struck me most was the smile she gave when I asked if I could take a picture (I opted to share the one of her working instead of posing). I could feel the warmth in her smile that seemed to bleed right back into the thread as she just kept creating.

She was easily in her 70’s or 80’s, and despite it being 9:06pm, it didn’t look like she had plans to go anywhere for a long time. Nor did I get the feeling that she wanted to. She seemed so at home.

She just looked so damn happy, proud, focused and calm. I noticed myself even a bit envious of how simple her life probably was.

But then I caught myself.

I was doing what I always tend to do – following the pattern most the world does without even realizing it.

For a few moments I fell in the love with the sliver of her life that I was able to see, giving no thought to the rest of the story.

I’m all for being inspired by the possibility of what people do for work, and that’s why we profile so many of them on LYL. Believing in possibility is where the journey has to start.

But what concerns me is that most of us tend to stop there. We give all the attention to the part of someone’s life that represents our own dreams, that we forget to notice what’s real.

And it might be the most dangerous with entrepreneurship…

The challenge is twofold:

  1. With today’s social tools, it encourages people to only post and share the top 5-10% of their lives. And since the spotlight is bigger and brighter the more successful and well-known you get, it only becomes more distorted over time.
  2. As humans observing our surroundings, we naturally seem to assume people have it better than they actually do. We magnify the glamor and marginalize the truth. When these two factors combine, it can be incredibly misleading.

So today I want to offer another look at it. An entrepreneurial reality check of sorts.

Because most of us know the glamorous stuff all too well. That I’m able to write this from a little cafe in a small beach town in Greece. You know about the freedom, travel and adventure. The influence, owning your own calendar, having no one to report to, choosing your own destiny and having unlimited possibility in how you build, create and apply yourself to the world.

That it’s actually possible to double or triple your income in a year (or a month) by getting creative with a new idea or approach. And to do all of this while feeling like you’re actually doing something that matters – and helping people in a unique and meaningful way. We hear about this stuff a lot.

And yeah, like we talked about last week, the possibility is downright mind-blowing, and I’m so damn grateful to be living right now as opposed to any other time in history. I wouldn’t change a thing.

But having false expectations and me painting some BS rosy picture doesn’t do any of you any good either.

Because if you go into it thinking it’ll be a lot easier and more glamorous than it is, you’ll start things for the wrong reasons and probably give up way too early.

That’s not what this community is about. That’s not what you’ve entrusted me to do. It’s about shedding light on the path, on what’s possible – warts and all.

The reality is entrepreneurship isn’t for most people. Sometimes I even wonder if it’s for me. The emotional and actual swings can be crazy – often times they are.

A while back one of our readers asked me…

“Didn’t you ever want to bawl your eyes out at some point back at the beginning?”

So I figured I’d shed some light on the side of the story that never gets enough attention.

crazy people work here

12 Reasons You Might Not Want to Be an Entrepreneur – or at least fair warning of the party you’re joining…

1. My short answer is yes, I did feel like bawling. And at times I actually did. I still get the feeling more often than I’d care to admit. The speed at which momentum can appear and then disappear is hard to get my head around. People doubt me all the time. I doubt myself too. Lots of people around me don’t understand what I do, or why I do it. It can make it hard to relate to others.

2. Sure I can travel more than I used to, but I’m turned on and connected more than I’d like to be. A lot more. Sometimes I miss the days of being able to go off the grid for a couple weeks, but even today if I did that technologically, I’d still be connected mentally, because for better or worse I don’t ever really stop thinking about what I’m building.

3. I constantly have to be innovating and reinventing. I wonder if the way I’m doing things still makes sense or if it’s time to change. I don’t know what this business or my income will look like in a year.

4. And while no job or career is anywhere close to certain, as an entrepreneur I am very very aware of that uncertainty every day. Often times it excites me, but every now and again it brings me to my knees.

5. There is no being off the clock. If things need to get done then you keep working.

6. You often go a very long time before getting any recognition. Almost no one paid attention to my work for the first four years. You have no idea what that can do to one’s confidence and conviction, especially when others are doubting you at the same time.

Gandhi says, “First they ignore you, then they laugh at you, then they fight you, then you win.”

But no one talks about how tough it can be to stomach those first three steps. And that the fourth is the only one not guaranteed.

7. Some mornings I wake up lost in what to do next. Or where to start among the endless and growing list. I can get crippled by the constant decisions, huge and tiny, that must be made with imperfect information.

8. Self motivating can get unbelievably exhausting. Sometimes it’d be nice to have someone to just tell me exactly what to do next.

9. Every day I realize there’s more to learn and seems like there’s less time to learn it.

10. I wear more hats in a day than I thought I’d wear in a lifetime. I got into this business because I wanted to help people find and do work they love. I didn’t realize I was signing up to be part-time manager, CFO, artist, writer, event planner, designer, box checker and box creator. I’m now grateful to have a team, but that still doesn’t make all my hats go away.

11. Your identity can become so tied to your business that it’s hard to distinguish between the two. A decrease in sales or traffic or growth sometimes impacts my own confidence and self worth. Even though intellectually I know one is not the other.

12. Wondering how sustainable the business is can be incredibly terrifying. The pressure of thinking how my ideas will support my family over the years is intense. That can keep me up at night and chase me out of bed in the morning.

If every moment were only like this innocent sign we came across in the little Greek isle of Paros…

no stress be happy

Not exactly. At least not all the time.

It turns out there is a not so glamorous reality of being an entrepreneur, of taking a stand, walking your own line and pursing what matters. And this is just scratching the surface – a mere nibble of what I’ve experienced in the past few years.

And I know I’m not alone, despite how few creators actually talk about it.

I’m beginning to think these experiences aren’t boxes you check as you grow. They’re more like cycles you experience in different ways on different levels along the way.

It’s like the path to mastery… Every growth and progress phase is followed by a plateau. But before the next growth phase there’s a dip. A phase where confidence wanes and you wonder what the hell is happening. Then more progress – at least that’s what we hope.

But don’t worry, this isn’t how it always is.

I pinch myself every day thinking of the possibility I get to be a part of. Of how I get to help and impact people with the work we do – and the meaning and life it’s provided for me and so many others. I’m grateful for all of that on levels I can’t describe.

But you deserve to see both sides. So that when things get crazy, you’ll expect it and welcome it as a part of the path you chose – as part of the party. So you’ll lean into it instead of darting for the door.

And it’s not all about going at it on your own.

I know many of you plan to build your own thing and a lot of you already are, which is awesome. The world needs it!

But remember, loving what you do comes from aligning who you are with the difference you want to make in the world. Whether that’s on your own or with someone else makes no difference. What matters is that it’s you.

Maybe you strike out solo from day one. Maybe you find a partner, or join a business already having the impact you care so much about making. In our lifetime we’ll all likely start with one and end with the other. And then perhaps do it all over again – backwards. It’s all possible. That’s the fun part.

It just depends on how crazy of a ride you’re looking to get into. 🙂


P.S. I was thinking of putting together a little quiz to see if you’re meant to be an employee or entrepreneur. Would that be helpful? Tell us in the comments – and let me know if you’ve experienced any of the above!