Starting a Business? Learn Lessons From These 3 Big ‘First Year’ Mistakes

October 7, 2015


One of the biggest lessons that I’ve learned from starting a business is that mistakes are inevitable. In late 2013 when I left my job to pursue my content writing side business, I knew that I would encounter obstacles—and that, statistically speaking, the odds were against me succeeding as a solopreneur.

Terrified of the ‘unknown,’ I put a lot of pressure on myself during my first year. I worked 16 hour days and spent all of my free time working on my business. I did everything in my power to take command of my destiny. On paper, I had a great first year in generating six figures in revenue. Off the record, I probably took 15 years off my life by letting myself succumb to anxiety, poor eating habits, and relentless intensity.

I was—and in many ways, still am—the worst boss that I ever had. I put myself on a self-destructive path and needed to course-correct.

Now in my second year as a solopreneur, I’m taking efforts to course-correct my bad behaviors. Step one of this process involved sitting down and confronting my worst habits. Here’s what I’m learning from my biggest rookie mistakes.

Mistake #1: I completely let myself go

In devoting my entire heart and soul to my business, I stopped taking care of myself. I ate takeout almost every day, pushed myself to sit for 16 hours a day, and developed horrible anxiety. Between an infinite customer pipeline and people wanting to ‘pick my brain,’ I was letting the pressures of the world control me, at the expense of my greatest strength—my optimism, happiness, and passion.

One day, I decided that enough was enough. Within the span of a weekend, I overhauled my eating habits, signed up for a kickboxing class, and connected with a personal trainer. After about two weeks of taking care of myself—even on days when I just wanted to stay home and work—I noticed a dramatic change in my mood. My anxiety was almost gone, and I felt a low-grade, constant sense of euphoria.

Not wanting to lose that feeling, I’ve continued eating right and working out—sometimes, up to 10 hours a week. I feel energized, healthy, and closer to my personal best. I’m more relaxed, clear-headed, and a better entrepreneur.

Mistake #2: I was chained to my fear of failure

When I became a solopreneur, I did everything in my power to reduce my probability of failure. I diversified my client portfolio, only hired freelancers instead of full-time employees, and encouraged my significant other to stay in his job. For the first six months in my new role as a founder, I monitored job boards for ‘backup’ opportunities.

In hindsight, my behavior was the equivalent of penny-pinching. I became obsessed with the idea of ‘outrunning’ a potential for failure that was nonexistent—when I should have been focused on expanding my business.

It took me six months to overcome this mindset. Every day, I practiced taking small risks—investing a tiny amount of money in certain stocks or ‘taking a bet’ on an experimental initiative that I didn’t know would work. I mustered up the courage to take one of the biggest ‘leaps of faith’ that I have ever taken in my business—asking my significant other to quit his steady, well-paying job to join my company as co-founder.

While I haven’t figured out a way to outsmart failure—the potential is still very real—I don’t let it hold me back. I rarely think about my backup plan if my business were to fail, and I’m comfortable making judgment calls without second-guessing them. I’ve begun to look at my failures as personal growth opportunities.

It’s not so scary anymore.

Related: Suffer from nighttime panics? How to keep them under control.

Mistake #3: I became obsessed with my numbers

Every time I lost a customer, I freaked out. Any time that I anticipated a dip in revenue, I would sit my co-founder down for a ‘serious talk.’ I checked my projections and expenses multiple times a day—even when I had no changes to analyze or report.

Related: How to cope with losing a big freelance client

I was wasting time, missing out on life, and forgetting why I went into business in the first place. Eventually, my co-founder knocked some sense into me by helping me realize that money isn’t everything.

Since this moment, I’ve weaned myself off my forecast spreadsheets, which I now check once a week. While I monitor expenses and growth opportunities, I am relatively hands off until the end of each quarter, when it’s time for my co-founder and I to pay estimated taxes.

I feel mentally free and am now making progress with my co-founder to pursue the direction in which we want to grow our business—by building a product.

Final thoughts

The biggest change in my attitude has been my mindset towards mistakes. At the end of the day, I am lucky to be in the position that I’m in—to be able to make a mistake in the first place. Mistakes keep me down to earth, make me smile, and help me remember how much I love the challenges that life brings my way. As an entrepreneur, I hope that I keep making, learning, and growing from them.


about the author

Freelance Contributor Ritika Puri is a San Francisco based blogger who writes about trends in business, internet culture, and marketing. She's inspired by the intersection between technology, entrepreneurship, and sociology. Follow her on Twitter.