The Three Things I Wish I Had Known When I Started My Business (Including the One That Damn Near Brought Me Down)

I perched on the edge of the bed, feeling the thin, cheap mattress sink beneath me onto the plywood board beneath it. Laptop on my lap, my fingers hovering over the keys in sync with the butterflies hovering in my stomach.

I was about to send in my very first paid piece of writing — and I was wildly, disproportionately nervous about sending this $3.25 assignment in.

As I hit send, watching the page cycle for what felt like ages because my Internet was barely hitting 1990s standards in 2009, I had no idea that this would be the moment that set me on a course that would see me running a business, traveling the world, and sitting here right now writing this to you from a fancy-pants roof garden.

I wouldn’t trade what I do for the world — but there were definitely some parts of the journey I could have done without.

So let me share with you the three things I wish I had known when I was sitting back there on that mattress:

#1. This is consuming

I can’t state this enough — because it’s one of those things that you read and you’re like “Oh yeah, I get it, it’s consuming.”

But no, it’s seriously, life-alteringly, wake you up in the middle of the night consuming. Starting a business requires so much more of you than I ever expected mentally, emotionally, and physically.

And as romantic as that can sound when you’re starting out, there always comes a time when you look up from the middle of a laptop with 65 tabs open on it, scribbled notebooks strewn around you and day four hair and think, “How did this become my life?”

If you stick with it, you figure out the systems and support you need to make sure that your life doesn’t stay like that — but I have yet to meet anyone who hasn’t had at least one moment where if they weren’t already sunk so deep into the process of starting and running their business, they probably would have walked away.

#2. Bootstrapping does not make you a better person

Oh did this one hold me back forever. So I had this idea that since I was founding this business, I should learn how to do everything in it — and I mean everything. I taught myself basic coding so I could build my first WordPress website. I taught myself social media management. I tried drafting my own contracts.

And while there is some merit in making sure you know how things work in your business, there’s only so far that DIY-ing it can take you, and when you hit that ceiling, you tend to hit it hard.

So I wish I had known to hire as much help as I could as early as I could, especially for things that (1) I’m not good at and (2) big picture strategic thinking, because it’s damn near impossible to get an accurate read on your business’s direction and potential when you’re that deep down in it.

#3. Ignoring the scary stuff is the worst thing you can do

True story: I once set the record for fines at my local library by paying over $100 because I had gone out of the country for three months with a library book and somehow couldn’t bring myself to go online and renew the damn thing until the window for renewal had passed.

Things like that — financials, legal stuff, the big scary stuff that a lot of us more creative entrepreneurs tend to get the shivers over — I tended to ignore. Or slap a Band-Aid over whatever issue was arising at the time and call it good.

And now-me looks back at then-me and wishes she could say “Do not do this, because it is going to bite you big time down the road!”

And it did. By not dealing with my fear of figuring the money thing out, I put myself in the type of tax situation that has you looking back through three years of statements, bewildered at that one month where you apparently kept Amazon in business single-handedly and absolutely terrified that the IRS is going to come and take you away with a bag over your head.

Luckily I eventually found the two best accountants in the world (because when I screw up, I screw up big, and actually had tax obligations to two governments), and they helped me sort it all out … for way, way less than I would have ever imagined.

So the lesson here? Don’t ignore the scary stuff. If it’s business-foundation stuff, things that involve governments and courts (aka legal stuff, financial stuff, etc.) get good help with it as early on as you can. It’s never as scary once you actually look the issue in the face and get some good help on your side.

 

I’ve come a long way from that terrible mattress and 1990s Internet — and I know you can create that kind of change in your life and your business too. You’re going to screw things up. You’re going to have moments where you wish you could walk away. And you may just end up with two governments asking you where their money’s at.

But, ultimately, you’re so much stronger, creative, and resourceful than you think. You’ve got this. Now go do great things!