10 lessons after 1 year of being my own boss

On this day last year, I handed in my corporate laptop and badge and trod barefoot into my new office. My home office—just steps behind my kitchen.

I had a handful of amazing clients I’d been working with for a few months, so I knew exactly what I needed to do on that very first Monday of my new entrepreneurial life. Except, I knew, and I didn’t. I had no idea what was going to happen the following week or the next month.

There were so many questions swirling around in my head. Uncertainty, creativity, and inspiration were my new modus operandi. This was a definite change of pace from rush, commute, meeting, do some work, more meetings, rush home, make dinner, get the kids to bed, and start working again.

In honor of my one-year-entrepreneur-versary, I spent some time reflecting on where I’ve been in a year, the lessons I’ve learned and where I’m headed next.

Here are the most important lessons:

  1. Just because you work 50 hours at an office job doesn’t mean you can do it at home. Working for yourself is very different when you work at home, mostly alone on most days. There’s no gathering around the craft beer tap or La Croix fridge to chat about the weekend or the weather. There’s me, my laptop, and my projects. I learned very quickly that my weekly max is 20-30 hours a week. If you’ve read the book Deep Work by Cal Newport, you’ll also learn that most of us can focus for 4-6 hours a day.

  2. Die Empty. Also one of my favorite books from Todd Henry—as much as I love my clients and the words I get to create for them, I dedicate a portion of every day to my writing. That could be my blog, a new book, writing for my website, or creating a new offer. I like to die a little each day… in a good way.

  3. Track your time. Having worked in management consulting where we had to track our time down to 15-minute increments, the habit stuck with me. And tracking my time is more important than ever. I know how long it takes to write a blog post each week, how long it takes to write a proposal, and how long it takes to write and edit a sales page, about page, or website. Time—track it.

  4. Get out. By the third day of being my own boss, I realized the only humans I had seen were my husband and the kids, and maybe the UPS guy. Now, I make it a point to work from somewhere else once or twice a week. Changing up the scenery with a new cafe keeps things fresh.

  5. Clean your desk off every night and at the end of each week. There’s something about the act of putting everything in its place at the end of the day to signal that it’s time to stop working. Same with the end of the week. Physically wrapping up a week’s worth of writing feels good.

  6. Plan your week on Sunday. Each Sunday, I look at the meetings for the week ahead and the work I need to do then figure out what I’ll do on each day to map out my entire week.

  7. Celebrate the wins. Every new client, fresh new project, opportunity, or surprise was jotted down on a special spot in my office. And each day, I write down all the things I’m grateful for, even if it’s a surprise check in the mail, a great connection with a potential new client, a mention on social media. Focusing on the wins constantly brings more wins.

  8. Have a plan. This one was hard for me because I’ve always been one who likes to wing it. It works out for me though, because I expect it to. More on this another time. When my business coach forced me to sit down and think through how much writing I was capable and willing to do each month, I could see what was possible.

  9. Get help. A long-time perfectionist, Jacq-of-all-trades, and someone who says, “I can do that myself,” more often than I should, hiring help is hard. But, you can only go so far on your own. In the past year, I’ve hired someone to do the tech stuff I hate on my website, someone to do bookkeeping, an accountant, and also a designer. By giving the work I don’t enjoy to people who do enjoy it, we all win, and I can focus on what I love to do.

  10. Unplug. I’m working on this one. The pull to work around the clock is always there. I very rarely work on weekends. If I do fire up my laptop, it’s to do some writing on a personal project. On most days, I keep my phone in airplane mode until I’ve had my coffee, written morning pages, and have done at least 30 minutes on a personal writing project.

Year 1 of being my own boss was pretty fantastic all around, and I’m even more excited and energized going into year 2.

Are you just beginning your entrepreneurial journey? Have you been on this ride a while? If you’re stuck and something’s not working quite as you’d expect, send me an email and let me know.

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