What does “success” even mean?

Today’s edition of Wishful Working is a 4 minute read.

Last spring, I wrote about my mixed feelings for the word ambitious. You can read the whole post if you want (it’s quite good, if I do say so myself), but I’ll give you the TL;DR:

I have never identified with stereotypical ambition in the context of my career. I do not desire a certain title, salary, or level of authority. And feeling alienated from the traditional, hierarchical career journey led to heaps of self-doubt and imposter syndrome.

Ultimately, I’m realizing I have plenty of ambition, but my definition of success doesn’t necessarily align with prevailing definitions. Especially since becoming a freelancer nearly three years ago, I’ve been thinking a lot about what success looks like for me in work and life. 

Here’s what currently comes to mind when I think about success:

• Success means having freedom, autonomy, and near total control of my schedule. I want to be able to do what I want, when I want.

• Success means working on projects (paid and/or personal) that are interesting, challenging, fun, and creative.

• Success means not having to check my bank account before making most purchases — because I have enough money, I don’t have many expenses, and I’m confidently aware of my full financial situation.

• Success means being mostly debt-free. I have some student loans hanging over my head, and I don’t think I’ll feel truly successful until they’re gone.

• Success means having warm, healthy relationships with my spouse, friends, and family members.

• Success means being able to travel a few times each year.

• Success means being stress-free and enjoying leisure time without any guilt or fear.

• Success means being able to give generously to support people and causes I’m passionate about — not hoarding wealth, but sharing it.

One of the things I’ve learned about success and lifestyle goals is that the bar can move in both directions. For example — Yes, I can earn more money to be able to afford the things I want, but I can also decrease my expenses and change my lifestyle to fit a lower income. And I can also decide to want fewer things.

Living in a super-rural, ultra low cost of living area doesn’t work for everyone, but it’s the situation I found myself in after meeting and marrying a Canadian farmer and moving to Saskatchewan. We might not live here forever, but while we’re here, our expenses are relatively low — as are our stress levels. It sometimes feels like a secret life-hack.

In one of their newsletters last year, Lex Roman mentioned their decision to reduce their annual revenue goal, a move that was only possible thanks to lifestyle choices like moving to a cheaper city, coliving, and happily forgoing homeownership, pets, plants, and kids.

I think many of us are sidestepping “keeping up with the Joneses” consumption and status signaling in favor of living in alignment with what we actually want in life. But it’s a constant battle, especially in a culture built on capitalism, consumerism, and competition. I am not a perfectly conscious consumer or minimalist, but I can tell I’m mostly living in alignment with my definitions of success because I keep having this “pinch me” moment:

I’m at home with my husband. It’s a typical evening. We’re in cozy clothes, and we’re making popcorn before putting a movie on.

“This is the life,” I say out loud, and I’m not being funny. I have everything I need. I’ve already “made it.” I wish I could bottle that feeling because it doesn’t always stick around.

We don’t need as much as we think we do, and we really don’t need to try to fit someone else’s definition of success. Pursuing success on our own terms is powerful and subversive, and operating from a place of abundance is life-changing.

What does “success” mean to you? I would love to know.

See you next week,

Kara

Kara Detwiller is a writer 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 or Bluesky. 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.