The Hole in the Boat

I went to a workshop one time about success as a woman in business. It was more life-coach-y than I expected, lots of woo-woo when I was hoping it would have concrete steps to success. However, one moment sticks out.

“Imagine yourself in a boat,” says the coordinator. “You’re going along like gangbusters in the boat of your business, but you have to keep bailing it out. There’s a hole in the boat somewhere! What is the hole?”

I immediately realized – it was internal stress about money.

Since then I’ve had “the hole in the boat” as a theme I needed to investigate inside my own psyche.


Even now, though, I’m ignoring it. I wrote the above and then abandoned this post. In the world of fight or flight, I am firmly prey, cowering and hiding from anything scary or difficult.


So what’s the deal? Well. I can sum it up in an anecdote. A chat with SS a while back, discussing options for my career. Do I stick it out at the job I’ve had since 1999? Do I try to find my way through being a small business owner in a small community on a small island? If I do, how does that happen? Leaving the security of a long-term job is a scary thing.

SS: So, what’s the worst that could happen?

Me: I could lose the house.

SS: C’mon, that doesn’t really happen! That’s like a boogeyman the bank makes up to frighten people.

Me: My parents lost their house when I was 18.

SS: …. oh.

My dad was an entrepreneur, and it ended poorly because he had problems running his business. I have a very similar makeup to my dad – a bit oversmart in some areas, a bit stupid in others, a lot distractible and forgetful and slack with details. Who’s to say I could do better than he could?

What makes me any different?


People talk about the huge amount of production and drive I have. I don’t see it. Instead I see dozens of opportunities I allowed to pass without follow-up. I see a to-do list that keeps getting longer, brilliant ideas sitting by the wayside. I see my inventory un-done and still incomprehensible to me. I see procrastination everywhere, and couch-surfing when I could be productive.

How can I possibly be capable of running my own business if I can’t manage to keep my socks clean and paired off?

Sometimes I feel like I could be a millionaire. I’m smart enough. I’m fast at production. I theoretically know how to market what I make, even if I don’t have time or follow-through. Other times – yeah. I figure if I lost a secure salary, I would drain our sad little bank accounts in no time.

The problem is this gap. The gap between Has A Full Time Job and Can Support Household With Business. The amount of work required to fill the gap is enormous (sometimes it feels mountainous and pass-less), and the time it would take to get things going, without a solid income but continuing bills, would leave us destitute. I could try to ramp up before I left the safety of my salary, but every attempt so far has made me exhausted – and discouraged at the lack of time in a weekend.

And there’s the other thing keeping the boat-hole open: security. Safety.  I don’t know if I can live without the security of a reliable paycheck.

Not to mention, I grew up relatively poor (not living on the street, but certainly without luxury) and I have rebounded into overspending. I have a stupid habit of buying things I don’t need. As a consequence, my credit cards give me the stink-eye every time I open my wallet.


Another question from that workshop was, “How would you do it if money was no object?”

I think about that a lot. I am not sure I have the answer. Which… maybe means entrepreneurship is not for me?


This is taking forever to write. It’s not finished. And the worst part is – there’s a block here. I have told this story more than once. And I’ve never gotten past this point. I’ll keep pushing at the wall, trying to find what it’s made of, looking for a weakness and a way through.