What I've Learned in My First Year of Freelancing

I can hardly believe that I am sitting down to write this. In the way that life tends to go, I feel like I sat down to write the post from my first month of freelancing yesterday and the post from the first six months of freelancing two years ago.

For me, crossing this milestone means a few things. Most importantly, it means that the mind game I’ve been wrestling with and which has been telling me that after the one year mark that I'll finally have a “real business,” can be silenced. Apparently, 365 days is when I feel I have arrived and no longer need to spend as much time trying to convince others this is real. More than anything else, this feels like it is a “whew” moment.

The “yay!” moment is that all of the sudden it also seems easier to imagine where I want to be in year 2, 3, 5, and beyond. I tend to be a milestone/celebratory kind of person in general, but I would say this is one of the biggest milestones I have encountered up to this point in my life. For that reason, I not only wanted to acknowledge the significance but also reflect on what I’ve learned in the past year.


Being your own boss is a special kind of blessing/struggle. I think what I notice most in this post vs the two similar ones I wrote earlier this year is that they were focused on processes and specific mindsets, whereas today I am more looking at the bigger picture, the lifestyle, how to do this and enjoy it for years to come.


This is a big one and, at the risk of sounding dramatic, is one that once it caught up to me, it took a while to rebound and correct. The best way I can describe it, is that it felt a little like getting a new car. At first you can’t stop drooling at the shiny exterior, feeling a little surge of excitement every time you put the key in the ignition, and basking in that wonderfully indulgent new car smell. But after a few months, the smell starts to fade, the car payments begin, and then the kicker…you spill your coffee all over the driver seat when you're running late. Now, before I linger on the negativity too long, my point is that the excitement of starting a business fades just like everything else. After all, you can still love your car and not want to vacuum it out once a week like you did when it was new.

My advice here is to make sure you set up sustainable systems for yourself. In the first few months, I was riding on this entrepreneurial high. I was checking everything off my list and then some. Looking back, I literally can’t believe that I rebuilt my website in addition to regular blog posting and constant social media management, not to mention handling client work. The only way I could manage that was by working nearly all the time. I wouldn’t say that I experienced an extreme burn out, but the process I created for myself simply wasn’t practical. I was working a regular 5 day week, doing some sort of administrative work on Saturdays, writing blog posts on Sunday nights, and networking or working on client work into the night regularly on the weeknights. It was a formula to accomplish A LOT, but as soon as I started to slip on maintaining this rigorous schedule, things started to fall by the wayside, primarily priorities for my business. My motivation levels were fluctuating and the rest of my life was wanting some attention too.

The fact is that when I started to realize that the tasks I was working on were things I would always have on my to-do list, I became a little disenchanted with what I was doing, a dangerous and unfortunate place to be. This is the part that took some time and effort to correct. The good news is, I learned a lot from that experience, but I would advise avoiding this mistake and really taking your systems and workflow into consideration from the get-go. Framing your on-going tasks as things you will have a long term relationship with is a great start - make sure you can hang for the long haul!

Have a life!

Similar to the above point, balance as a business owner is going to be a key component of living a happy life. For the first few months I was ok with, and proud even, that my business was my hobby. I like working hard, so why wouldn’t I like doing that all the time? (Feel free to insert an obvious answer here).

After all, it’s a fortunate position to be in, to want to spend time on your business and value the growth enough to prioritize it, buuuut I got bored. I tend be a person who needs a lot of variety so I was surprised by my initial laser focus. Then, I was less surprised when I needed to mix it up.

Since graphic design is my career and my business, I don't do as much as I used to in my free time, but I still love to create, especially hands on projects. I have thrown myself into some rewarding DIY and home makeover projects in the past few months and have found it is the best way to keep my creative juices flowing and my feelings of stagnation at bay. I would absolutely suggest seeking a hobby that excites you to keep things fresh!

Evaluate, Evolve, Grow

You never stop evolving - and it’s a good thing!

In the first couple of months, I had this confidence in my process and presentation. I was so sure I had it all figured out. Check check check - mic drop! While it wasn’t entirely untrue, that feeling began to fade as I started to challenge myself more. In those first few, very vulnerable months, it was important to tell myself I had the perfect, secret formula. It was the boost I needed to put myself out there. I encourage finding those pockets of confidence and trusting yourself but NOT at the expense of evolving, learning, and improving as a business and as a business owner.

For example, every couple of months I have been evaluating my branding package. While the deliverables look about the same, the process and presentation have come a long way and each development has improved the client experience. Now, I know to anticipate this always being the case. Finish one project, then evaluate how it could be done it better.

You learn the value of money

This is simple, but I couldn’t make this post without mentioning finances at least once. When it’s there, it’s great. When it’s not, it’s the worst. The stress of being entirely responsible for your financial well-being is something I believe will be with me for as long as I decide I will continue being in business for myself. I should mention that I am coming at this from having a loving and unbelievably supportive spouse, which in a way alleviates some financial stress but in a totally different way adds the burden of guilt over pulling your own weight. No matter your scenario, this will come up. In the last twelve months, I have been fortunate that the extent of this stress was a weight on my mind at times rather than a reality of making rent or buying groceries.

But the fact of the matter is, when you are in charge of your income, you have the ability to recall a story about where every dollar came from, how you earned that business, and the hours that went into those dollars. It is equal parts all consuming, stressful, and (best of all) empowering and satisfying. Like I said, I don’t think it would be very honest not to mention that regardless of how it works out for you, the finances and the many burdens associated with it can’t be overlooked as a freelancer or business owner.

You might complain less

Honestly, it's kind of random that I noticed this at all, but once I did, I decided I would make this a focus. I first noticed when I was going through the process of renewing my license plate tags. The long and short of it is that it was a long, annoying process. Somewhere along the course of this three-month long undertaking, I realized I hadn’t seen anyone except my husband consistently enough to give daily updates on this car debacle.

That was when I realized, if I had seen this or that person every day, I would have complained about this issue to them. They would have heard every juicy (ehem, boring) DMV detail, every frustrating setback, and my every over-the-top emotion about it. Honestly, once in a while, this lack of outlet frustrated me, but eventually helped to train my thoughts to be ok with processing this or that internally and reserving valuable friend time for more significant updates.

You might have to be more intentional about spending time with others

Directly correlating to the above observation is this one, and honestly, the above statement has been my way of putting a rosy face on creeping feelings of isolation. On the one hand, I think we can all agree it’s great to complain less. However, in reality that meant I was sharing less with people in general, simply because I was seeing people less.

One of the challenges I hear a surprisingly little about is that being a solopreneur means you are solo. Being a fairly extroverted person and coming from a very close knit office setting, this has been a hard adjustment for me. I became used to having a core group of people that I saw at least 8 hours a day, 5 days a week. We chatted throughout the day, shared things about our lives with each other, and became close in a way that is hard to avoid when spending that much time together.

I know that there are plenty of people who aren’t bothered by this, but if you are one of them, I would say it is extremely important for your long term mental health to have a solution that works for you. For me, the most effective answer has been to join a coworking space (seriously the best!). In addition to that, making sure I don’t neglect happy hour with friends or lunch with a new colleague has been huge. Basically, as I work on fine tuning my work flow, it’s meant shifting some of that focus to intentionally spending quality time with others.

You might meet some really amazing people

My favorite unexpected development? Because I'm a person who thrives in a tribe, I knew from the get-go I needed my own little “Good Day Tribe.” I have been so fortunate in meeting some really amazing people, some of whom have become great friends in the last year simply because of the overlap in our business ownership. The reasons for having business besties is huge, but some of the people I've met have extended far beyond a business camaraderie and have become friends to not only share business wins/losses, but to share life with. These people are friends AND role models, and that is more than I think I could have hoped for.

Just keep putting yourself out there

Two weeks ago when I published a blog post, I turned to the colleague sitting next to me and confessed, “This still makes me really nervous. Every. time.” Then cringing, I hit publish. (And today. And next time...)
Being a business owner is extremely personal. Being a solopreneur may be even more so. Everything you do is literally directly connected to you…which at times makes every decision feel like it will make or break your company. The reality is, that’s almost never true. The biggest thing I have learned is to continue to trust yourself. You go into business for yourself for a reason and the common thread among every type of business and every individual is that we believe we can offer something valuable related to our own expertise. Don’t forget that! Then when you do forget, cut yourself some slack and remember.

Are you in business for yourself? Are you thinking about it? What are your fears or stories of successes? Please share, I would love to hear in the comments below!