The Entrepreneur Struggle Is Real*

*Caveat: actually, it’s not

Photo by Lauren Mancke on Unsplash

I jumped right into entrepreneurship at the deep end.

But that’s what you have to do, right? Leap, and the net will appear. Even right back at the very beginning, the words of Jen Sincero rang in my ear, reassuring me I’d done the thing I needed to do — that I was a “bad ass” — because I’d jumped before I was ready. Because (and here’s the secret) — you’ll never feel ready.

So there I was. In the deep end from the beginning. House sold, embarking on a new worldwide adventure, launching my online business. Deep in relentless doubt, uneasiness, fear, and the newness of it all — and clinging on to it in that seemingly endless free fall.

For a good long while, what felt like an eternity, that became my new normal, my new comfort zone.

Is this a familiar story? For me it seemed like the rites of passage every entrepreneur must go through. Being scorched by the searing flames of entrepreneur initiation.

All the business books I’d read referred to it in some form or other. All of the personal development ones too.

And as much as I’d love to say otherwise, there’s no shortcut through it. Not one that I found anyway — other than to say the first 2 years of business were an exponential learning curve.

By comparison, in the same period of time, law school doesn’t even come close. I can’t remember a single useful thing I learned in those 4 years that I can use today.

But like law school, it challenged me and pushed me further than I thought I could go.

To chase “the dream”, to work for myself, I had stepped away from my extremely decent full time job — to have more time, to have freedom.

But in the early days, instead of living the dream, 150% of my time was taken up with overwhelm:

  • free training,
  • paid for training,
  • reading,
  • coaching time,
  • mastermind time,
  • list writing,
  • list reviewing, and
  • list staring.

The last on the list involves using as much precious time as possible to peer at the ever growing lists of tasks that never get done, perpetually rolled over, and growing longer by the day, stewing in increasing anxiety and overwhelm.

It went on for like that for a bit.

Like 2 years of leaping, free fall, and waiting for the net not just to appear, but to also remain in place.

There were good months, bad months, and scary months.

There were months when I asked for help, and was told (like this month), with a sincere apology, that I “should be managing”.

But in those first 2 years of business, in that deep end — that’s a big ask.

Most people aren’t managing at the best of times.

And the hard truth about the first few years in any business is that it can be a rollercoaster.

Not all of it was easy, or nice, or comfortable. On a daily basis I had to buckle in my seatbelt, occasionally reinforce it, or talk myself off the ledge and not hit the emergency eject button.

But I’ll say this — it was worth it.

That digital nomad wanderlust thing didn’t turn out how I was expecting, not at all.

Our first 4 weeks were spent in Montenegro — I envisioned getting fit, spending my days hiking, getting tanned, and spending 1 — 4 hours per week with my clients, gracefully earning lots of money and sustaining this fabulous lifestyle.

Reality check — it was 44 degrees Celsius even after Heatwave Lucifer turned down the dial.

Running a business takes a fair degree of effort — probably more than the four hours per week that Tim Ferris sold me on.

I left whiter than when I landed (I think), scarred from countless mosquito bites, traumatised from the temperatures (I am Scottish), I was sleep deprived, and getting fat because I was too lazy to learn the Montenegrin for “I am Paleo” , and smoothies still hadn’t made it big yet.

Even on the darkest days, not really.

I got travel weary — yes. Living out of a suitcase is one thing, but running a business out of a suitcase that contains all your worldly belongings takes it to a whole different level. I cart my life around with me, and that gets exhausting.

But there are ways to minimise that pain — slow travel, long term house sits, giving myself a few days or a week each time to ease into new places (that’ll be my next post…. Travel Tips for Introverts.)

I doubted myself for a long time — yes. And after two whole years of living with it, it only recently subsided.

But there was a moment last year, while I was having a beer at the spa hotel in the mountain resort I had just checked in to, it dawned on me.

This isn’t that hard.

I actually caught myself trying to convince myself that life, business — everything — was such a struggle.

But here’s the thing.

Hard is the story you tell yourself.

Yes, things might be challenging.

But you make it twice as hard when you constantly repeat the injury to yourself.

Very few of the things that any of us need to do are actually hard.

Taking action is most likely the easy bit.

The hard bit is all the worry, the anxiety, the limiting beliefs, the doubt, the fear, the overwhelm.

Doing all of the tasks, doing them unsupported — yes that can be hard. But what is much harder is just not doing them — and then berating yourself because you haven’t done them.

In his book, The War Of Art, Steven Pressfield calls this the resistance.

Resistance is hard.

But everything else is actually, most likely, easy.

So the struggle isn’t real — not as real as it seems anyway. The struggle is usually in your mind.

The sooner you can come to terms with what it is you are resisting — and my bet is that it’s owning your own brilliance and putting it on display for the world — then you can start to take action, build momentum, and enjoy the ride.

That’s right around the point that your business takes off.

And finally, after all those times you thought you needed it most, that’s when the net appears.

Founder, feminist, entrepreneur, coffee + self care

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