5 Mistakes I Made In My First Month Of Being Self-Employed

entrepreneurs mistakes

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—and what Fiverr readers and sellers can do to 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.

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. There couldn’t be a worse 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.” But here’s the problem: many of us need these kinds of arbitrary deadlines or we’ll never leave the 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 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 job.

3. I Didn’t Work for Half of It

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 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 and 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. My old ones needed some work:

Crispy illustration
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 skills 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. Though it ended up working out great, it was distracting and 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.

Thinking about taking the leap? Check out what Fiverr has to offer.

Katherine Penta
Brand and copy expert with over six years of experience developing brand personas, managing content, and writing copy for brands like Neutrogena, Visa, and Adobe.
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Fiverr helped me a lot to start on my own when I finished studies.
Thanks for this chance, the article is very nice as well!


Fiverr is my main income. I got some more orders compared to other sites when I first started with Fiverr. It helps to pay my bills. I thought I was on the right track and then I hope more orders to come but still same or may be not good at all, even though I satisfied my every customer and did my best. so I guess I have to evolve now.


my account is disabled what i will get it back please help me.


Hi Hamza,

Our Support team is ready to help you with this. Could you send a request over to http://support.fiverr.com/hc/en-us/requests/new



Thanks for this good tips


I was hoping for more general advice, these are quite specific issues that are unlikely to rise for most people. For example, I certainly can’t afford a trip to Patagonia…

Would have more useful to address real issues like, underselling yourself, awkward client meetings, panic about not being good enough. That would have been more useful.


good tips.


The world i would like to say i love Fiverr, it’s such a great and largest place to do part time job and also full tine.


Great article. Thank you


GOOD Article


So needed this … going through it now.


I think fiver is very best way of income. Thanks


very helpful article.


Thank you so much for taking the time to write this great article! It was very helpful.


We did lot of mistakes when starting freelancing. But I think this article helps to avoid mistakes and understand what are the mistakes when doing Freelancing.


it helps me lot. thanks