Freelancing = running

A couple of Sundays ago, I ran my first big race: a 10K.

If you would’ve asked me a few years ago if I ever saw myself as someone who runs “for fun,” I’d give you a disgusted look and go about my day.

Today? I still wouldn’t say I’m a full-fledged runner.

But I did enjoy working toward a goal and can see why running is therapeutic (being alone with your thoughts on a long stretch of road leaves you no other choice than to question every life choice you’ve ever made).

I’m sure you can see where this email is going. Being a writer, I naturally found a theme between freelancing and running:

It’s a marathon, not a sprint.

How Running a 10K is Like Freelancing

It can take years to get the hang of freelancing.

Freelancing is not about quick wins and achieving your goals right away. There will be a lot of ups and downs throughout your freelance career — and plenty of times when you want to quit.

I felt the same way while running! A ton of ups and downs and many (many) times when I wanted to quit throughout the six miles.

Below is a glimpse into my inner monologue while running the race. I think you’ll find a lot of similarities to freelancing.

Mile 1: Let’s do this!

At the starting line running on pure adrenaline and excitement. I’m ready for this — I’ve trained and (I think) I know what I’m getting myself into. It’ll be fun, right??

Mile 2: Okay it’s getting hard already (but I can do this) 

Wow, I didn’t think it’d be this challenging this early into the race. How come no one warned me about that massive hill? At least this next mile looks flat, hopefully I can maintain a steady pace.

Mile 3: Oh no, everyone is going faster than me…am I behind?? 

Why does it feel like everyone is passing by me? I thought I was doing okay! Maybe I’m not doing enough.

Mile 4: I can’t do this 

Why did I decide to run this race? I’m cramping, I’m so tired, and this isn’t fun anymore. The finish line seems so far away…maybe I should just walk instead. It’ll give me time to think about a different hobby or form of exercise I should try, because running is NOT IT.

Mile 5: Alright, took a water break — maybe this isn’t so bad 

Turns out, I just needed a quick break. Now I feel refreshed and ready to push through.

Mile 6: I’m getting the hang of this!! I can go a couple more miles 

Maybe it’s knowing that the finish line is near that’s getting me through, but I finally feel comfortable and motivated again. Maybe running is fun after all?

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For me, these miles represent each year of freelancing. (A 10K is 6.2 miles, and I just so happened to have six years of freelancing under my belt, so this analogy worked out ~perfectly~).

Making the leap into freelancing is exciting. The first year or so is full new experiences, feelings, and learning skills you didn’t know you had.

The next couple of years is where it starts to get challenging. You start to experience the downsides of freelancing:

• Losing a client

• Chasing down invoices

• Paying estimated taxes (💀 worst part of freelancing IMO)

• Comparing your journey to other freelancers

• Burnout

By year four, you may or may not want to continue freelancing. For me, this is when I started to question whether I should continue or try to find a traditional 9-5.

It wasn’t until last year that I finally started to feel comfortable and confident in my career path.

These thoughts and feelings could also represent all of the ups and downs you experience during a hard year, month, or even a week. Freelance life is truly that unpredictable at times.

But it’s a long game. Freelancing gets better the longer you’re in it, the more comfortable you get marketing yourself, and the more you understand your skills and what you want out of your business.

• For Starters is one of my new favorite newsletters. It highlights small businesses and people pursuing cool ideas. If you’ve ever dreamt of starting a small business, reading these stories will give you a ton of inspiration and motivation (personally, my dream business is a combination book store/vintage shop/cafe — wbu?)

• my mind is actually a recommendation that came from the For Starters newsletter. It’s a bookmarking extension that lets you save literally anything you come across online. My aesthetic-driven self loves how visual it is!

• I just ordered this “invisible” laptop stand. Not terribly exciting but being in your 30s means your workspace has to be more ergonomic vs. aesthetic (unfortunately).

I’ll be back in your inboxes on April 29th 💌 In the meantime, let me know what you’re working on and how I can help!

Rough Draft is a bi-weekly newsletter where I share tips and musings on creating a freelance career from scratch. Subscribe here. You can also find me on LinkedIn, Twitter, Threads, or my website. 👋