When you've got a big ship, you're going to need a crew.

 photo by  Juli Arendash  for Cleveland Flea

photo by Juli Arendash for Cleveland Flea

I sit around, knowing that I have knowledge to share, but immediately doubting myself.

“Yeah, but who cares what I have to say?”

“I’m still figuring this whole thing out, I’m not an expert.”

“I have so much do to, shouldn’t I stay focused on my lengthy to-do list (much of which includes trying to be a good boss)?”

My answers to each?

I care what I have to say– and so will all the other people who are working diligently through issues like this.

Everyone is a work in progress, that doesn’t mean you haven’t accumulated knowledge and experience that makes your contribution valuable.

Most of my writing is inspired by what I’m going through today but also what I’ve managed to get through on my 6-year journey as a business owner. I’ve struggled mightily, always keeping my head down, feeling discomfort and questioning myself. And letting the voices of others question me.

I’m done with that. My constant re-curring thought after I get through something hard?

“Trust yourself.”

So, my writing will begin to celebrate my hard-won victories, questions that I’m struggling with and much more of my personal life (because, yes, I am committed to having a personal life AND a fast-moving startup).


I had no clue how big my business would be. I have this really funny characteristic that puts me in all sorts of sticky situations.

I believe in the impossible.

No task seems too big.

Nothing fires me up more than someone doubting me or telling me that something is impossible.

Impossible is an opinion.

Let me say that again. Impossible? That’s an opinion. It’s not fact. And I’ve been doing the impossible for my entire life.

But this belief of mine often gets me into predicaments where I’m doing things that require more than what I have– more experience, more time, more money, more patience, more sleep, more help, more understanding, more empathy, more of it all.

And I found myself running a BIG business (in effort not in the number of employees). In all honesty, I probably wouldn’t have it any other way. I want to make an impact on this world. And I’ve always been drawn to large scale shifts AND details. You see, I LOVE the details. I think that’s precisely why I’ve struggled the past 6 years as a business owner.

The scale of my project made the details almost impossible.

It’s what this work has asked of me. To let go of the minute in service of the large-scale. I didn’t want to take that lying down, obviously, so I worked myself to the bone. I exhausted myself in service of my desire to make the details obvious to others.

Sometimes I succeeded.

Most times I did not.

I thought I could do it alone. I thought I SHOULD do it alone. I thought I didn’t deserve support, that if I started this, I should fix it.

But I was sailing a big ship all on my own. Running from bow to stern, putting up the sails, steering the boat, cleaning and keeping passengers happy AND doing it all with little to no experience aboard a ship.

The seas were most always rough, just adding to my exhaustion but delivering me high confidence after getting through each storm. During them, mind you, I was terrified. But I had no choice but to keep my ship afloat.

I think this is often what it feels like to be a small business owner, and then the founder of a growing startup. I had no idea what I had gotten myself into.

But I rather like my ship now and I’m proud of her.

At some point, I resigned to the fact that I had to hire a crew. But I had no time. No energy. No experience. AGAIN.

And if you’re a small biz owner you know you’ll find yourself in this type of predicament over and over again. Lacking what you think you need in order to solve your newest problem.

You have two options.

  • Stay where you are, and stop moving.

  • Find a way to solve your problem and keep going.

I chose to solve my problem. It was super hard for me. But let’s see where I ended up.

In January of 2018, I began the season with a pretty battered ship. Everything felt torn and damaged and dirty and sad. I had luckily hired one person who believed in me with her whole heart. That was enough to sustain me. Plus, she knew a lot of really great people. And what she knew about them was that they loved BIG. They were kind and committed and talented. And she knew that was exactly the type of person I needed to hire coming off a particularly rough season.

Here’s how we prepared to hire.

  • I wrapped my brain around the fact that YES, I did want a team. I had been resistant until then. My brain was focused on how I’d support these people. I was scared. I let that fear guide me for far too long.

  • Once I was FULLY committed, I was able to find ways to create more time, more money, more knowledge. If you’re panicked or really scared, creativity does not come easily, if at all. But if you can coach yourself into a space of positivity, and love and excitement, clarity comes along with it.

  • I drew up job descriptions and made them pretty, actually. I like creating internal business documents that are branded to businesses. It gives me confidence that I’m getting to the details of things.

  • I also found a way to describe what I was looking for, and what type of business my company actually is. That’s a really hard thing to do sometimes. At least, I’d struggled with it. But I found ways to celebrate the type of startup that I was, that I wanted to be, that I sometimes had felt shame over in the past.

  • I carved out time in my schedule for the hiring process. It DOES take a lot of time and energy, truly. But I also believe that if you want to preserve (or in my case, create) company culture that you, The Founder, must do the hiring. I had wanted to make this other people’s problem for a long time. I didn’t want employees. Again, going back to my first point. I HAD to stop resisting my circumstances. I had a large small business. And a large small business requires extra hands.

  • I self-coached around my money thoughts. And I have to continue to coach myself daily. My negative thoughts around money made me not want to hire in the first place. Just because I now have a team doesn’t mean the thought has gone away. It’s now being threatened daily, so it fights back. When my staff makes mistakes that cost the business money, they say, “See? You shouldn’t have hired this person.” And to that I say, “Fuck you brain. People aren’t perfect, and there’s a training phase.”

You get the drift. The things that come my way as a boss are sometimes seen through these old money thoughts. I notice them though. And I question them.

Yes, it’s tough being the captain of a fast-growing startup. But it’s a lot better with a crew that helps steer the ship and enjoy the seas with you.

 photo by  Heidi M. Rolf  for Cleveland Flea

photo by Heidi M. Rolf for Cleveland Flea