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5 Regrets from My First Month of Self-Employment

Updated on February 3rd, 2022
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Self employment is a victory for people who value setting their own priorities and schedules.

But it’s not without shortcomings. Drawbacks include lack of paid vacation or benefits, tax season nightmares, confusing or fickle clients, inconsistent work and many others. Until we address these setbacks, we’ll tread water and cut profits.

This article describes my own learn-the-hard-way methods so you can avoid the same blunders.

But first, a disclaimer: Different things work for different people. Take my experience with a grain of salt, because only you know you. What held me back could be your greatest opportunity.

5 Regrets from My First Month of Self Employment

1. I timed my leap around a “meaningful” date.

I became self employed in January 2016. Why? Because it coincided with the new year and was the equivalent of a nice round number. New year, new me. That’s a terrible reason to pick a date. Choose to leave your full-time job when you’re ready to leave your full-time job, not when it “seems like a good time.”

Here’s one problem with that strategy: many of us need these kinds of arbitrary deadlines or we’ll never depart status quo. If that’s the case for you, instead of picking a nice-sounding start date, pick a different metric: income. Break down your budget and determine the minimum consistent, predictable income you need every month to make it. Once you consistently attain that number with your side gig, it’s time for your two weeks. Remember, if you leave without a sizeable side income, you’re not self employed; you’re unemployed.

2. I didn’t have a hard stop.

Unlike many who choose self-employment, I enjoyed my day job. When it was time to leave, it was hard to say goodbye. So I didn’t. For the first two months I worked at my old job for 15 hours a week. My attention was split and my creative output compromised beyond measure. It was an enormous personal strain for little professional reward; I felt like I was just getting by. As much as I liked my work, it would have been better for my company and for me had I put a hard stop on my time there.

3. I didn’t work for half of self employment.

I had surgery that left me bedridden and loopy for a few days, and a week later I went on vacation. The surgery was bad enough, but unavoidable. The vacation timing, which had been planned far in advance, was within my control. I should have quit my full-time job at least a month or two before taking a vacation, or I should have waited to quit until after the vacation. Or I shouldn’t have gone.

Hopefully no one else is naïve enough to think that you’ll get work done in Patagonia. Once I returned, it took me a week to re-acclimate and return to my old industriousness. You may think that when you’ve been working really hard you need a vacation, but physics disproves this: it’s called momentum. If you’ve been working hard, not getting anything done and suffering from burn out, it’s time for a vacation. But when you’re on a roll, vacation saps you of your fuel and spits you back at square one.

4. I decided to learn a new field.

I decided I wanted beautiful, crisp illustrations to accompany my blogs and articles. So I decided to buy a drawing tablet and learn Adobe Illustrator. Why then? Sometimes self employees suffer from imposter syndrome: we convince ourselves that we have no idea what we’re doing and no skills. So we furiously gather new talents with the hope that people won’t notice how incompetent we are.

Instead, I should have focused on my writing—what I know and love and profit from. When you make the leap, remember the one or two skills that made you unique and valuable. What do you call yourself? Writer? Plumber? Stick to one thing. No one is a writer-plumber—at least in her first month of self employment.

5. I got a partner.

Invigorated by infinite opportunity and equipped with newfound time, I partnered with a Twitter connection for some marketing consulting. The partnership was eventually distracting, and it was frustrating to be so split between my freelance work, developing my own personal brand and my partnership. The whole point of being self employed is to be on your own and not beholden to other decision-makers. Give yourself that freedom before jumping into bed with more obligations.

But, ultimately, we can’t wait for the stars to align before taking the leap. The most important thing I did in my first month of self employment was to do it. However you choose to make it, I wish you foresight or, at the very least, the power to learn from your mistakes.

Caroline Beaton

Caroline Beaton

Caroline Beaton writes on the psychology of millennials at work. With equal parts statistics and story, she helps twenty-somethings stop wasting time, figure out their purpose and create a livelihood around the life they want. She writes for Forbes, The Huffington Post, Psychology Today and her blog, The Gen Y Mind, where she covers early career crafting, self-development and young entrepreneurship. She also provides high-end consulting and content marketing services for brands seeking to connect with millennials.

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