The Self-employment Struggle

Being self-employed can be tricky.  In the (nearly) three weeks I’ve been without a boss I’ve had days of huge productivity and days of zero productivity.  For a while I thought working for myself would mean a flexible schedule, with lots of time to do whatever I want.  Indeed if I so desired I could put 60+ miles on the bike every morning, wearing compression tights while I sit at my computer and code for the afternoon and evening.  Or I could travel all over the place, see friends endlessly, and live the good life.

What I’ve described above is the self-employment struggle — no clear deadlines or outside pressure, nothing but self-induced desires and goals.  The urge to stay-cation is huge, yet productivity is critical.  I should be the busiest I’ve ever been in my life right now.  The only way I’ll succeed is by building awesome shit, enabling me to have more meaningful conversations with investors.  I quit my job to give myself the time I need to prototype ideas and speak to investors.  I didn’t quit to get more free time.  Self-employment, at least the kind that will hopefully one day lead to a technology startup, is about working hard, not taking a vacation.

  • I was working freelance for a bit, so I had deadlines, but still had to manage my hours myself. 

    I think the tough part is really nailing down short term and long term goals. Starting at birdseye view, and then zooming in until you can have some yearly goals that can be broken up. Of course, each level can be modified as you go along but it gives you a feeling of direction. I have a 50,000 feet list (by the time i’m 90, what have I accomplished?), a 20,000 feet, and 5,000 feet (in three years, what have i accomplished?).

    Once you have some basic short term plans, you can create objectives to meet and break them down into actionable tasks.

    I recommend: 

    – writing 3 actions to get done each day, that makes you happy to leave “the office”- filling up your day on a calendar and abide by it
    – i mix personal and professional, so i have a jam-packed day, but i’m including my fun stuff too (“by when” i need to finish a book, my running goals, etc). And schedule free time, if you’re worried about having to packed of a schedule.