The Mistakes I Made in My First Year as an Entrepreneur

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Even though I’m well past my first year of running my own business as a freelance writer, I frequently reflect on that first year. I’ve found that by looking back on the mistakes I made during that first year of entrepreneurship, I can learn some very valuable insights. Luckily, these mistakes aren’t all that hard to avoid if you know how to look out for them. Keep reading to learn from my business mistakes!

Mistake No. 1: Being Quiet

If I could go back to my first year — actually first day — in business, I would rent a megaphone and start spreading the news. I was so nervous that I would fail as a freelancer and need to go back to working a 9 to 5 (please note there is no shame in the consistent-income game!) that I didn’t share the news of my new business with my professional network. It took me six months to get up the courage to post a simple LinkedIn post. Within minutes of sharing that post, a connection reached out to inform me she didn’t realize I’d left my job to freelance and that she wanted to hire me. To this day, I still work with that brand, and they have commissioned thousands of dollars' worth of work. That revenue would have made a big difference in those early months — not just financially, but confidence-wise.

Mistake No. 2: Not Outsourcing Work

No entrepreneur can do it all, and as tempting as it is to hoard the profits you worked hard for, investing in your business is worth it. I did everything on my own that first year, and I now realize how counterproductive that was. In my second year of business, I hired an accountant to make tax season way less stressful, and doing so has given me so much peace of mind and saved valuable time.

Of course, I can’t hire professional help for every area of my business that challenges me, but I do pay for a few different softwares that make running my business more manageable. My latest splurge is a monthly subscription to a voice-transcription software. At first glance, the annual cost wasn’t something I was eager to pay. But after just one month of using the software to transcribe interviews I need to conduct for my stories, I’ve already profited from this purchase by saving hours of my time that would have been spent on tedious transcription work.

Mistake No. 3: Saying Yes to Everything

In the first year, I said yes to every opportunity that came my way, including working with clients who didn’t align with my goals, taking too low rates in order to gain experience or exposure, and agreeing to way too many coffee dates and networking calls that led to nothing. Sometimes saying no leaves the time and space for more important endeavors. I’ve found that every time I let go of a lower-paying opportunity, I have more time to pursue higher-paying projects. As a result, my income shoots up!

Mistake No. 4: Setting Too-High Expectations

As a creative freelancer, I’ve noticed there are certain unfair expectations of what running my business should look like. While many of these expectations come from outside parties, I have been guilty of fueling these fires, as well. When working for yourself, it’s easy to fall into a trap of expecting every area of your new work life to be better than if you worked for someone else.

Once I let go of the idea that running my own business had to equate to high pay, amazing work-life balance, and zero stress, those goals fell into place. But I needed to relinquish them early on in order to focus on the work that needed to happen to build a business that could support all of those goals. The first year of running any business will be exceptionally challenging and that is an important fact worth accepting. Just know that it will get easier.

By the time my second-year business anniversary rolled around, I was making three times what my last salaried job paid, had great work-life balance, and only worked with clients that I loved. I sure wish I learned to trust the process sooner!

Tags: Tips from Women Executives

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Written By

Jacqueline DeMarco

Jacqueline DeMarco is a freelance writer based in Southern California who graduated... See Full Bio

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