4 Essential Life Lessons I’ve Learned Through Running a Business

I could write a book about all of the new business, management, and sales skills I’ve gained in my four years of running Word of Web. But the most important things I’ve learned are more personal and more abstract than that. Here are some of the biggest life lessons running a business has taught me.

1) Let yourself feel the highs and the lows

Running a business creates really high highs, and really low lows. It comes with the territory. Nothing feels better than closing a big deal or producing an exceptional result for a client. Conversely, nothing feels worse than losing the deal you spent months pursuing, or getting tough feedback from a client. Early on in my Word of Web journey, I decided (subconsciously, I think) to dissociate from the lows so that they wouldn’t affect me as much. Whenever I started to feel disappointed about something, I simply boxed it up and put it away so that I could move on to the next thing. Although I think this is a healthy practice to some extent, what I found over time is that it made me feel apathetic about the highs, too. All of the sudden, I wasn’t feeling much of anything with my business. It all became a bit stale. In my attempt to numb out the hard stuff, I had numbed out the good stuff, too. Over the past few months, I have worked hard on letting myself feel each emotion fully – no matter what side of the spectrum it falls on. I won’t claim to know that this is the right strategy for everyone, but I will say that it has made a night-and-day difference in my business and my life.

2) Be brave (and humble) enough to apologize

Mistakes happen. They just do – no matter how hard you work, how many hours you spend checking, or how many eyes you have reviewing the final product. I’ll never forget the first time I made a mistake on a client’s project. I was horrified and spent hours thinking of how I could somehow pretend the issue had never happened – or that it wasn’t our fault. Honesty is one of my biggest values, so ultimately, I decided to be frank with the client. I explained the mistake, accepted full responsibility, apologized profusely, and offered a path forward (with some financial reparations included). I braced myself for a verbal thrashing, but instead, something amazing happened. The client thanked me for owning up to the mistake and accepted our new proposal without question. I’ll never know for sure, but I’m convinced that if I hadn’t owned up to the mistake, I probably wouldn’t be working with that client anymore. Client relationships are a lot like personal relationships – you’re only as good as your word.

3) Be accommodating, but not deferential

I used to be a big-time people-pleaser. I rarely stood up for myself or did anything that would rock the boat in social situations. (I thought that this was the easiest way to keep the peace and avoid confrontation). But being the CEO of Word of Web has knocked those tendencies right out of me. After all, you can’t run a successful business if you’re constantly letting people walk all over you. Throughout my Word of Web journey, I’ve learned to challenge comments about my age, stand by my pricing, confidently express my opinions, and speak up when a client insults me or one of my team members. And interestingly enough, I’ve started to see these skills pop up in my non-work life. It’s like I’ve developed a new muscle – and now its strength is showing up in ways I had never imagined. Time and again, I’ve seen that standing up for myself doesn’t come at the cost of making people happy. Being assertive is not the same as being antagonistic.

4) Don’t blindly accept someone else’s idea of success

I have never dreamed of turning Word of Web into a billion-dollar business empire with hundreds of employees, investors, or offices across the country. I love that we’re a small business that can develop a close relationship with each of our clients and maintain a close-knit team environment. But throughout my time running Word of Web, I’ve felt a ton of pressure to grow and scale and sell. I’ve felt guilty for “only” working 8-hour days, for taking vacation, and for wanting to stay lean. Admittedly, some of that pressure is internal, but a lot of it comes from news articles and podcasts glorifying business owners who fit the typical entrepreneurial mold. To be clear, I’m not saying that archetype is bad. In fact, I think it’s great for certain types of people and certain types of businesses. What I am saying, however, is that fitting into this mold is not the only option. It is not the definition of success. As a business owner, it’s on you to craft your own idea of success, and build your business accordingly. It’s the same with your life.

Final Thoughts

I always knew that businesses reflect the people who run them, but I’ve been surprised to see how much my business has guided my personal growth. This is my list of reflections as of 2023 – I’m looking forward to seeing what it looks like a decade from now!

PS – check out our new podcast, The Founder Factor, to hear other entrepreneurs speak to topics like this.

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