Why some freelance advice sucks

Last week, fellow freelancer (and fellow Saskatchewan resident) John Loeppky shared his thoughts on knowing the limits of your expertise as a freelancer. Or, as he elegantly pitched it in his initial message to me, “How one handles when freelancers talk out of their ass about how the industry works on LinkedIn.” Lol.

John described a few reasons why people spread misinformation* about the world of self-employment. (*I won’t say “lies” because it’s not always deliberate.) In my experience, these ass-talkers fall into one or more of the following categories:

Naive Newbies

These are the folks who jump into freelancing and immediately start sharing advice based on their limited experience. I actually don’t notice this very often, but I was once subtly accused of being a naive newbie early in my freelance journey: 

In a Twitter thread, I shared that I typically work 15-20 hours per week. A seasoned freelancer said that wasn’t realistic and implied that experienced freelancers work 40+ hours/week. 

Joke’s on him because I’m still happily and successfully working 15-20 hours/week. 😇

Manipulative Marketers

These are people who deliberately share misleading or untrue information because they’re trying to sell something. I see this one a lot. A certain LinkedIn ad comes to mind, one that says you should stop calling yourself a freelancer and become a “Premium Ghostwriter” (barf).

There are also a number of guys (yes, they are usually men) who are essentially “selling the dream” — boasting about their success so that they can sell a course that teaches you how to succeed like them. Spoiler alert: their success comes from selling courses to suckers. 

I call it the pyramid-schemification of freelancing.

Clueless Conformists

Some people just repeat what they’ve heard before without critical thinking, fact-checking, or acknowledging nuance. Here are a few things I often see parroted:

• You need an LLC!

• The best way to scale is to start an agency!

• You have to niche down to be successful!

• Never charge hourly!

• Start your day at 5am!

• Post more videos!

• Post more carousels!

• “Freelancer” makes you sound cheap because it has the word “free” in it! (I hate this one.)

These things can be good advice, but they’re often presented as universal freelancing imperatives and they simply aren’t. There is very little one-size-fits-all advice in freelancing.

I want to be clear that I’m not trying to be a gatekeeper or the LinkedIn police. You can post what you want, and you don’t need to censor yourself for fear of getting it wrong. Here’s what I will recommend: 

Humble confidence.

I first came across this phrase in a hiring post from one of my favorite apps, YNAB. Every role they advertise asks for a “Humbly Confident ________.” (Ex. Humbly Confident Content Writer 😉) Is it a little corny? Maybe. Is it a great way to frame the balance of self-assurance and willingness to learn? Absolutely.

Humble confidence looks like sharing what you know while acknowledging that you don’t know everything. It means being open-minded and open to feedback. It might also mean simply not weighing in on a topic if you don’t know what you’re talking about. 

I really like the exercise John presented in last week’s newsletter. He identified three truths about his work life and is using those to guide what he shares online. 

Here are three truths about my own work life that guide my online presence:

• My worth is inherent and not dependent on productivity, output, or outcomes.

• I share my personal experiences and things I’ve learned while avoiding prescriptive, one-size-fits-all advice.

• I’m actively de-centering work in my own life and encouraging others to reject hustle culture.

These truths represent my values. If I post things that align with these truths, I’m pretty sure I’ll be posting things I’m proud of.

This is a great topic that gave me a lot to think about. Big thanks again to John for starting this conversation last week!

See you next week,

Kara

Out of Office

What I’m doing when I’m not working

• I was in Canada for July 4, which felt weird. My extended family back in Iowa always does a big get-together, and I hate to miss it. However, I spent time with my husband’s family instead, and it was a really nice day! My mother-in-law even made apple pie for the occasion 🥧

• I’m going to visit my family in Iowa next week! It’s a 17-hour drive to get from Saskatchewan to Iowa, and we usually split it into two days. It’s a lot of driving, but I love a summer road trip!

• We started painting our house (exterior) a month ago, and we’re still working on it… It’s a big job! The north and south (front and back) walls are now finished, which feels great! I got unreasonably excited to buy new door handles, outdoor sconce lights, and house numbers last week.

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.