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Breaking down barriers to self-employment
Freelancing should be more accessible
Kara Detwiller
September 12, 2024
Today’s edition of Wishful Working is a 4 minute read.
Early in my career, the thought of working for myself seemed like an unachievable goal. It felt too risky and unstable and overwhelming. And a disastrous one-off freelance project as a recent college grad put a bad taste in my mouth about the whole thing.
My eventual path to full-time freelancing involved overcoming a number of barriers, both through hard work and through random life circumstances. A lot of stars had to align for self-employment to be a viable option for me.
Over time, it has become abundantly clear to me that this path is simply inaccessible for many, and frankly, that sucks. In this newsletter, I want to address some of the things that prevent people from choosing the self-employment path and propose some ways of overcoming those barriers.
Barrier #1: The On Ramp
Problem:
The beginning of the self-employment journey can be rocky, and it can take a while to earn enough to cover bills and expenses.
Solutions:
Start doing freelance projects before you quit your FT job, so you can build up a client base before taking the leap.
Before leaving your FT job, save enough money to cover expenses for several months.
Get a part-time job, so you have some income to augment your (possibly meager) self-employment income.
Reduce your living expenses — move in with parents, relocate to a lower cost of living area, rely on a spouse’s income, etc.
What I did:
Like many people, I did a combination of things. I had some money in savings to cushion the beginning of my journey and cover early expenses (like the new laptop I desperately needed), and I have a spouse whose income can cover our basic living expenses (which are fairly minimal because we live in a rural, LCOL area).
Barrier #2: Healthcare
Problem:
In the USA, healthcare is tied to employment, and paying for healthcare coverage as a self-employed person can be prohibitively expensive. Some people may want to work for themselves but can’t justify foregoing employer-sponsored health insurance.
Solutions:
Honestly, the main solution here is for the USA to catch up with basically every other developed nation (and many developing countries) and offer some sort of universal healthcare. 🤷
Until that happens, aspiring freelancers and consultants will have to do their research to find a suitable health plan and include that as an expense when preparing for full-time self-employment.
What I did:
My path is not exactly the most relatable or replicable, but I married a Canadian and moved to Canada, where health coverage is free and not tied to employment status. (No, I was not specifically looking for a Canadian to marry. It just happened that way. 😂)
Barrier #3: Income Variability
Problem:
Freelance income can be unpredictable, and it often varies from month to month. It can be hard to cover expenses in lean months, and it’s stressful.
Solutions:
Reduce the variability by taking on retainers, building in recurring (“passive”) income, or taking on a part-time job.
Embrace the variability by saving up to get through lean months.
On a more systemic level, something like a Universal Basic Income could help reduce variability and enable more people to become freelancers and entrepreneurs.
I cover this idea in more depth in these newsletters — Riding the Income Roller Coaster and RIP PTO.
What I do:
More than two years into freelancing, I still don’t have this one nailed down. I am experimenting with ways to diversify my income streams, and I keep a decent chunk of change in a HYSA to help cover expenses during slow months. But I would like to save more to feel more stable.
I dream of a future where more people can become independent contractors and entrepreneurs without facing such undue stress and precarity. Yes, it’s hard work, but I believe many people have the grit and determination to be successful.
And I believe we’ll get there.
See you next week,
Kara
Wishful Working is inspired by my desire 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.