Two Weeks Off

Like many entrepreneurs, I love running my business. Even though I have other interests, I have so much fun at work that I struggle to turn it off and take a break for more than a day or two.

So, this holiday season, I decided to unplug from it for two whole weeks. No email, no project, no helping my team at all. Here's what I learned:

1. The Team Doesn't Need Me Every Day

For the most part, I'm not involved in day-to-day tasks. We now have 8 full-time team members (10 in January), so they can cover most of the critical job functions on their own. While the team is new, they've been around long enough to answer 95% of the questions they might have without me.

This made me feel really good.

2. We Still Need More Redundancy

While I was out, one of our teammates in a customer-facing role had a personal issue that led to an unplanned absence. I would normally have been the backup, so we dropped some balls while trying to backfill here.

We need more redundancy in our key roles, but we don't quite have the budget for two people and a team lead in every function.

3. Some Tasks Are Really Hard to Delegate

For example, I'm trying to move to a new payroll provider and get the core team on W2s. Dealing with state and federal tax agencies, filing paperwork, and proper accounting can only be outsourced so far. I still had to answer some questions on my own and it's hard to imagine how a part-time person could do all of this without my input.

As always, building a company is a never-ending project, but my goal this year is to get to a point where I can take 4 weeks off without issue. This will be a great testament to my team's ability to self-manage and ensure that I'm not the bottleneck on any critical parts of the business.

If you've gotten to this point, let me know. I'd love to hear your tips/thoughts!

Karl Hughes


Software Engineering