I love it when my team takes time off to ensure they are well-adjusted, balanced humans.

No, never mind I actually hate it.

An honest confession from a founder who is bootstrapping. It’s just how I feel.

Every founder who is bootstrapping knows their cash position better than their 3rd child (love you, E!). When you pay someone to not work in the early stage of a company, you feel it.

Do I want my team to take time off? OF COURSE! But it’s tough to cover, both financially and logistically. I don’t know if I’d feel the same way with a full-time team of 20+. I can’t quite remember what it was like when I was building alongside a larger team that had found a to summit an insurmountable workload. I do know this, though. Right now, if I want to show a profit / get momma some new shoes / get a babysitter and enjoy a nice date night, I can’t hire anyone to pick up the slack.

What it looks like when people on my team take time off:

• All the work + meetings fall on the founder’s lap… As if we don’t have enough going on already.
• If your company has a service component that helps fund other aspects of your business, your “billable” team members taking time off is a double (no, a triple) whammy.
• The few clients and partners you have feel the missing presence and ask, “When is so and so back?” I complain right along with them.
• The occasional silver lining. You realize you can do without… so you plan for a more profitable future without that role.

As an employee, a teammate taking PTO is an inconvenience. As a founder, it’s far more existential… pointing out the fragility of the business you’re trying to build. In the early stages threats lie everywhere.

The biggest threat to your model may be your best people taking a few weeks off. Here are a few valuable questions to ask yourself before you get too far down the path:

1. What happens when employees 3 & 4 both need PTO at the same time?
2. Can the company handle one of the key employees having a family emergency?

Embarrassingly, I didn’t think through those question as soon as I should have when I was starting Firm Studio. I hope you can think those answers sooner than I did and put yourself in a great early stage position.

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