5 Things I've Learned from My First Year as a Solopreneur

This month on June 13, The 5th Sense turned one year old!

I'd like to tell you that I threw myself a cute little business birthday party, but that would be a lie. I was back in Tennessee—where I grew up— for the week for my brother's wedding, and it was nice to return home, reflect with family and realize how far my business and I have come since I posted this blog 365 days ago

Anyone who's run a business from scratch on their own will tell you that you learn an infinite number of lessons in the first 12 months, and I'm sure that they'll continue pouring in through the years that follow. However, I do remember how much I enjoyed reading posts like these when I was just getting started— and I still do now! So today I'm sharing 5 of the biggest things that my first year of running my own copywriting business has taught me. 


I talked about this some here and here, but I can't say this enough— the only way to succeed in owning your own business is to be as self-aware as possible. There's a lot of advice on the internet— and plenty of it is great— but not every method, tip or piece of advice is going to work for you and your business.  

Here are some questions I would consider asking yourself and the people who know you best. Revisit them again every couple of months to be sure you're being honest with yourself. 

  • What are your strengths and weaknesses? (in business and personally)

    • Are there business weaknesses of yours that could be better outsourced?

    • Are there books you can read to help with those personal weaknesses?

  • Do you work better in a structured environment or can you truly be productive at home?

  • Are you the type of person who will feel isolated working from home? If so, how will you combat that?

  • Do you handle rejection well? If not, what are ways you can pick yourself back up after a loss?

  • Are you providing a service that the market truly needs? Or did you choose your services based on what you think is best instead?

  • Are you good at saving money for a rainy day?

  • Is there a new skill you can learn to better service your clients?

I've found that many of these answers can be found by taking the Myers-Briggs test (try out a condensed version for free here) and others can only be discovered through trial and error. The most important thing is to be honest with yourself— if something isn't working, stop doing it and find another solution. 


I explained some of the preparation that I did to launch my business in my three-month check-in post, but there's definitely lots that I've picked up on since. There are plenty of other resources out there about getting an LLC, starting a business bank account and filing your taxes. I'm not here to discuss that kind of preparation. 

The kind of prep I'm talking about it beyond that. If you're reading this, you've probably read a few of the thousands of posts discussing the benefits of running your own business, but have you read up on the drawbacks? 

It's easy to picture a blissful world of choosing when you work, how you work and who you work with. And all of those things are great. But, I would urge anyone considering going out on their own to prepare themselves for a different reality.

  • Do you know WHO you're really targeting? (Hint: "everyone" isn't an acceptable answer)

  • Do you have a sales plan to steadily find new clients so you aren't out-of-luck (and money) when one ends their contract?

  • Do you have a plan to retain the clients you currently have?

  • Are you ready to hear no a lot?

    • Do you have a strategy for staying positive when faced with rejection?

    • Are you prepared to change things up when enough no's show you that an idea isn't working?

  • Do you have a back-up plan or savings for months that you're down?

These aren't meant to be negative, they're meant to be realistic/honest (see point 1). 


If I haven't reiterated it enough— no matter how great your business idea is, you're going to hear "no" a lot. Sometimes you'll work your butt off to close on a client and lose it last minute. Other times you'll have one quit unexpectedly for reasons that may be out of your control. It's one thing to prepare yourself for it, but it's another thing entirely to be able to forgive yourself after it happens. 

I've gone into this story pretty in-depth in this post, but to sum it up— I hit a "business rock-bottom" at the end of last year. From a combination of things that were and weren't within my control, I wasn't motivated, taking care of myself or investing time in finding the right clients. As a result, I lost some business, had to dip into our savings and felt super defeated. 

None of that got better until I went back to step one (KNOW YOURSELF) and finally forgave myself for having that set-back. Ebbs and flows are an inevitable part of running a business, but being able to forgive yourself and bounce back is what matters most. Say it with me, "My worth as a person is not entirely measured by the success (or lack of) in my business." Say it again. Keep saying it until you believe it. 


 I swear, half of running a business is asking yourself where all the time goes. With no boss or department dictating your day-to-day, it's easy to get lost in distractions or what I like to call "productivity porn"— which is basically when you spend your day reading articles about business strategy or being productive, but you don't actually accomplish anything.

Without a boss to keep you on track, you have to monitor yourself. The best way to do this is to track everything— your time, your expenses, your incoming sales, your work flow, your work-wins, everything. To fix any problem— be it a structural, time management or something else— you have to first be aware that it's even there to begin with. Tracking is a great way to start. 


This is important. Arguably the most important— YOU MUST BE YOUR BIGGEST ADVOCATE. If you don't believe in yourself and your business, how can you expect anyone else to? 

I know, sometimes this kind of self-love advice can feel hippie-dippy and unproductive. But it's not. When you enter a room, you need to be ready and WILLING to sell yourself. If you don't believe that you've got the best services out there, how can you hope that anyone else will buy into them? You can't wait around for someone else to instill this confidence in you or sell your business ideas to others on your behalf. You built it yourself - now go show people how f*cking awesome you are by advocating for yourself. 

What's the biggest lesson you've learned from your job (entrepreneurial or otherwise)? Let me know in the comments!