February 28th, 2020
I took the last 3 days off (during the week) because I was hosting a friend in my hometown.

When I planned for this, I (naively) thought I would be able to squeeze in some work in the early morning or at night.

But I didn't. And the whole time I felt really guilty and had almost a feeling of withdrawal symptoms.

For me, I have a feeling of betrayal to myself when I take time off like this. I feel that for every "missed" day, that's important progress lost. I feel like I will have to make up that time, and now it will just take 3 days longer to reach my goals.

I also feel like I'm betraying my customers, sponsors, etc. What if they knew how much YouTube I watched or knew that I took the day off to go skiing? That time could be spent building a new feature or doing more marketing.

^^ I realize these thoughts are pretty ridiculous, but it's the truth.

I can't imagine that I'm the only one here. I can only think this would be even worse if you had a really tough boss you wanted to impress, or investors/mentors that had money on the line on your new company.

During my "time off", I legitimately had to step away for a couple hours and "catch up" with the business.

I told my friend to take a couple runs and I just sat in the car on my computer and caught up on email, etc. I literally sat in my car outside the ski resort and worked for two hours. How sad is that? After I got that work done, I didn't feel any better either.

And it's funny - doing this, I realized that almost everything could wait until I was back, and the sense of urgency I had was 90% in my own head. But it was less about emails piling up, and it was more about me feeling guilty that I wasn't working.

But it's not all bad, moments like these really help me realize what parts of my business rely on me, and that I need to continue to outsource/hire/automate so that it doesn't need me. I consider these to be "holes" in my business.

I also need to get better at planning time off. If I plan some time off in advance, it will actually inspire me to "get ready" for this time off and fix a bunch of things so that they can run without me. When I took 3 weeks off last year, I hired someone at Starter Story to manage most of the editorial process - they still run it and it has helped us scale so much.