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5 Things I Learned After One Week of Self-Employment

{Spoiler Alert: It's my dream job but it wasn't all a dream.}

“That’s not your school anymore, Mommy,” my three-year-old reminded me as we passed by my old building on the way to daycare.

The parking lot was filled with teachers’ cars; I recognized every one of them and longed to stop in, say hello, see how much my kids had grown over the summer. It was the first day of school, and I’d usually be welcoming new students at this time, but today, I drove right past, rocking an oversized sweatshirt and unbrushed hair (and no bra, mind you).

One of my old coworkers brings her daughter to the same daycare as ours. As I unloaded Theo, then Viv, she pulled into the driveway. She wore a dress and her hair was combed into a neat ponytail.

“How’s your writing going?” she asked.

I paused. I thought long and hard and tried to reach into my brain for something inspiring.

“It’s… it’s… well, I look like this,” I said, making a sad sweeping motion around my person.

What I was trying to say was:

  • The writing is going hard, and

  • The writing is going slow, but

  • The writing allows me to wear forgiving waistbands!

Let me try to be more eloquent here than I was in the daycare driveway. Here’s a list of 5 things I learned this week since leaving my job as an educator to work as a freelance writer, and some encouragement for you, too, if you’re new to being your own boss.

  1. The day goes by really fast, so make a plan. On the first day of my new life, I got groceries after dropping the kids off. When I got home, I put them away and prepped a lasagna for some friends. By the time that was done, I was hungry myself, so I ate lunch, then remembered I need to work out, and so on. My brain pinged from one task to the next and I was carried through the day on a current of chores. When the day was done, I had managed to squeeze in approximately 20 minutes of actual ‘work.’ Is this how it’s going to be? I lamented. It didn’t feel like a very auspicious start. The next day, I made a plan. I was going to be in control, not all the whimsies floating through my head. I made a list of the big, job-related things I needed to accomplish, and set a time to do them. I filled in the margins with household chores and enjoyable activities, and BAM! I knew how the day was going to go. I breathed a sigh of relief - organization is remarkably liberating.

  2. Tackle the difficult jobs first. Midweek, I spent an entire day agonizing over a difficult task that I needed to complete but desperately wished to avoid. I scheduled my easiest jobs first, telling myself that I’d get rid of some mental clutter by crossing those things of my list right off the bat. But it didn’t work. Instead, my mind was filled with the angsty clutter that inevitably comes with procrastination. I couldn’t commit myself to the tasks at hand because that undesirable job was looming ominously at the end of the day. The next morning, I decided I needed to just get ‘er done. I tackled the hardest task on my to-do list and found that the rest of the day had a sense of airiness and ease to it. I did a hard thing in the morning, and I got to revel in the relief that it was done for rest of the day.

  3. Throw perfection out the window. It can be crippling, I tell you, to sit at the starting line and try to figure out how to write a book or create a business or grow an audience from zero. There are too many options - it’s like one of those Choose Your Own Adventure books. [I always read all of the endings as a kid - I preferred to be sure that I had, in fact, chosen the best adventure. I’d like to do the same with my career - sigh.] Since they haven’t made a way to skip to the end of our life’s work yet, I realized I had a choice to make: I could keep sitting immobilized at my desk, listing every foreseeable obstacle, failure, and shortcoming, OR I could lunge ahead. I’d probably leave a wake of mess and mistakes in my path, but at least I’d be making some forward momentum. I imagine that when it comes to creating something new, giving ourselves permission to toss perfection out the window and allow for some mess is really the only way to keep moving. So I’ve committed to choosing that option.

  4. Take time to do the learning. I’m an educator through and through, so you’d think that I’d be all about learning new things. But as it turns out, it’s one thing to be the teacher, and another thing altogether to be the learner. Learning, I rediscovered this week, is HARD. And it is slow - so, so slow. I hate slowing down. I’d rather bulldoze my way through life. But there are some things that are worth taking the time to learn. Things that will help us advance toward our goals, or reach more people, or grow our knowledge or hearts or character. This week, I slowed down to learn how to:

    • Write sales copy

    • Use Substack

    • Understand bookkeeping basics

And as much as it pained me to pump the brakes to spend the time learning these things, and although I have nothing glitzy to show for it, I have a quiet sense of accomplishment that I now know more than I did on Monday.

5. It’s important to note what’s being gained (besides money). When I made the decision to make a career out of writing, I also made the decision to walk away from a comfortable salary (and health insurance). This has been hard for me. When I was earning a salary, I felt proud of the contribution that I was able to make to our family’s finances. It gave my days a feeling of value and worth. It gave me the feeling that I could treat myself to fun ‘extras’ like facials or new clothes because I was bringing in income. This week, I received my last teaching paycheck. Done. Finito. I’m not gonna lie to you - it hurt. While I know that my value to my family goes beyond how much money I’m able to make, my achievement-oriented personality needed to do some reorienting. To help with that, I made a list of all of the things that were gained this week as a result of this decision to work for myself. Here are just a few:

  • Theo and Viv got to sleep late this week and we got to read books together in the morning rather than rushing out the door.

  • Our family got to eat supper together at the table. The food was homemade and healthful. [Our three-year-old ate a Brussels sprout - win!]

  • I was able to move my body and exercise each of the five days.

  • I read for fun.

  • I had the flexibility to bring family members to appointments.

  • I was able to handle tantrums with more patience and love because I felt more rested.

  • I did not experience the Sunday Scaries.

Money is an important thing. I like making it. But it helps to remember that money is not the only important thing, nor the most important thing.


With any life change, there are pros and cons. As Emily Freeman wisely noted in her last Instagram post, we don’t have to be 100:0 about our decisions in life. We can be 51:49 - in other words, we can recognize that our choices are not all good or all bad - some of them are just a little better than the other, and we have to embrace the wins without lamenting the losses too much. Do you work for yourself? What have you learned along the way? Comment with your tips and hints to help all of us newbies!

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