How I got started as a freelancer

Today’s newsletter is a response to a question I got through my Ask Me Anything form! 

Let’s start with a “your mileage may vary” caveat. Each person’s situation and journey is so different. What worked for me might not work for you. But I’m happy to be transparent about my own experiences.

Years before freelancing

I earned a BA in Advertising, but you absolutely don’t need a degree in marketing or advertising to be a successful freelancer. I know many freelancers with degrees in something different, like education. I know other successful freelancers with no college degree at all. 

My first few post-college roles were more design-focused, but I also got experience with content writing, social media, SEO, PPC, and other marketing disciplines. Again, relevant full-time experience is helpful but not strictly required for success. 

My pal Sam freelanced part-time while interviewing for full-time roles after college, and she ended up becoming a full-time freelancer. She’s never had a traditional 9-5 job, and that works great for her! (Sam’s newsletter, Rough Draft, is one of my favorites. I recommend her recent post, Every freelance gig I’ve ever had.)

Right before freelancing

At the end of 2021, I quit my full-time job at a marketing agency in Des Moines, Iowa, got married, and moved to my husband’s hometown in rural Saskatchewan, Canada. 

Yeah, it was a lot of change in a short amount of time. 😅

Because of the immigration process, I wasn’t authorized to work in Canada for a while. I could, however, work remotely for US-based companies! Thus began my on-ramp to freelancing. 

Full disclosure: I was able to take basically five full months off between my full-time job and my freelance launch. This was only possible because I got married and my husband and I could live off of just his income for a while. I know this is not typical or feasible for many people.

If you’re single or otherwise can’t afford an unpaid sabbatical, your runway to freelancing will look different:

• You can find freelance clients and build your business before quitting your full-time job, like my friend Alyssa, who freelanced on the side for years before quitting her 9-5. (Her newsletter, Time Intentional, is another favorite.) 

• You can save up a nice cushion before quitting your full-time job to take some pressure off.

• You can get a part-time job that brings in a chunk of reliable income while also giving you time to freelance.

• You can move in with family, get a roommate, or move to a lower cost of living area to decrease your expenses (When my friend Lex, who is self-employed, moved from California to Georgia, life got a lot more affordable).

What I don’t recommend is quitting your job one day and launching your freelance business the next. There are many ways to start freelancing, but you need an intentional runway and some sort of cushion/safety net so you’re not immediately panicking and scrambling to pay your bills.

The first few months

1. Get organized

You don’t need much, so don’t overthink it. There are a million and one tools out there, but I recommend starting with the bare minimum: An email account, a LinkedIn profile, a simple website, a way to manage projects/deadlines, and a way to get paid.

I personally use Framer’s “mini” plan for my website and Moxie for basically everything else (project management, time tracking, accounting).

2. Find clients

This can of worms should (and probably will) be its own post, so I’m not going to camp out on it here.

My quick tips:

• Sign up for a few freelance jobs newsletters. My favorite by far is Freelance Opportunities (most of you already know that one because it's a major referral source for Wishful Working). I also like WriteJobsPlus, which costs $5/month but is well worth it, imo.

• When applying for jobs or cold pitching, share 2-3 highly relevant samples, not just a generic portfolio link. I’ve gotten multiple gigs simply by showing potential clients that I can do exactly the type of thing they’re looking for.

• A lot of clients find me through LinkedIn, so I highly recommend being visible and active there (posting, commenting, and connecting on a daily-ish basis).

3. Find community

Freelancing can be very lonely. You need to find your people!

• On LinkedIn, follow the freelance thought leaders and experts, but connect with peers — people who started freelancing around the same time as you and are on a similar “level.” These people will likely be more open to casual, virtual “coffee chats” where you can learn from each other.

• Twitter had a great freelance community circa 2021/2022 (RIP #FreelanceChat), but I believe there are groups of friendly freelancers on Bluesky and Threads now. I’m finding it difficult to juggle different social platforms since Twitter’s demise, so I’m focusing my energy on LinkedIn.

• I live in the middle of nowhere, so I don’t have much advice about in-person networking and coworking. But it sounds lovely lol 🥲

In my experience, success in freelancing requires a perfect storm of circumstances and a good deal of luck. Shoot me a reply or submit your follow-up questions anonymously.

See you next week,

Kara

Out of Office

What I’m doing when I’m not working

• My small town’s main librarian is on vacation, and guess who the substitute is? I’ve been working a few shifts lately, and I really enjoy it. Shelving books is so peaceful. Doing a storytime and craft for preschool children is less peaceful, but fun nonetheless. 😂

• Chappell Roan’s new song The Subway features a Saskatchewan mention, and it feels like our 15 seconds of fame. Have you heard it yet?

• I am not normally into cooking and baking, but I recently decided to attempt a basic white sandwich bread loaf. It turned out so freaking good. Shoutout to my friend Caitie, who sold me her beautiful yellow KitchenAid mixer. 🍞 

P.S. Got a question about self-employment, anti-hustle culture, business books, or something else?

Kara Detwiller is a writer and creative based in small-town Saskatchewan. She specializes in long-form content writing for enterprise SaaS, cybersecurity, and manufacturing clients. She is also working on her first novel, among other creative pursuits. To connect, reply to this email or find Kara on LinkedIn. To support her work on Wishful Working, share this email with someone or buy her a “coffee.”

Why Wishful Working? I write this newsletter because I want to see more people enjoy a life not centered around work. For some, the path to freedom and flexibility is through self-employment, but we also need to challenge cultural norms and champion healthier working conditions and work/life balance for all types of workers.