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The best (and worst) boss I’ve ever had
Spoiler alert: It’s the same person
Kara Detwiller
October 17, 2024
Today’s edition of Wishful Working is a 3 minute read.
Yesterday, October 16, was Boss’s Day. Throughout my career, I’ve had good bosses and mediocre bosses, but there’s one boss who stands out as the best boss I’ve ever had.
Funnily enough, she actually started out as the worst boss ever.
Honestly, she didn’t really know what she was doing. To be fair, she was a new boss and had never managed anyone before.
She was really hard on me and held me to impossibly high standards. She had some old fashioned ideas about work and productivity, and it led me to the brink of burnout a few times. She also kept me busy, so I didn’t have a lot of time to explore areas of interest and develop new skills.
But as time went on, she became a much better boss.
She helped me figure out when I’m most productive during the day, and she became very flexible with my schedule. She encouraged me to take time to follow my passions, and she adjusted my workload accordingly. She gave me lots of opportunities to grow and even a few raises!
If you haven’t caught on yet — I’m talking about myself.
I’m my own best and worst boss ever.
Some of the best advice I stumbled on early in my freelancing journey came from a podcast episode entitled “Rethink Work.”
“Most of us, when we step out and we have the freedom to shape our freelance businesses, we really have to do a lot of work and a lot of unlearning from the patterns and habits we’ve learned from employers.”
In the same episode, Megan also mentions that, as freelancers, we have been conditioned to treat ourselves the way that employers treat us.
Whoa. 🤯
Before going freelance in 2022, being an employee was all I had ever known. The longer I worked for myself, the more I realized I needed to stop treating myself like an employee and start seeing myself as a boss.
I also started questioning everything I knew about work. I stripped my work life down to the proverbial studs and rebuilt my schedule and processes in a way that works for me, to hell with tradition.
I’m still hard on myself, and I still sometimes find myself trying to measure up to other people’s definitions of success.
But I love having full ownership of creative and business decisions, and I even love wearing many hats in addition to my main “writer” hat — operations, project management, sales, accounting.
I love creating and curating my work environment, from my physical office and desk area to where I hang out online and how I network.
Most of all, I love aligning my work with my own personal values and goals, not corporate and shareholder priorities.
Basically, I love being my own boss. And I’ve become a damn good one. ✨
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.