Truly Scary Bosses You Shouldn’t Be To Yourself

Three ways that you’re showing up as a terrible boss to yourself.

Sophia Sunwoo
3 min readNov 30, 2021

I’ve had a couple of moments of burnout this year. I didn’t overwork or overextend myself, I was just exhausted between mentally juggling running a business, navigating a global pandemic, and so much more.

These past 19 months have been a marathon, ripe for burnout for absolutely everyone. I just watched a friend document her 14-day quarantine in a hotel room where she couldn’t even open a window — it was jarring to watch, to accept this variation of a new normal. This new reality we’ve been rushed into has deeply changed me this year and has shone a hard mirror on who I am as a business owner.

One thing I’ve deeply felt this year is that I am a pretty terrible boss to myself. I’m great at it when I’m managing other people, but I suck at it when I’m bossing myself around. This is what I’ve been reflecting on lately when it comes to being my own boss —

“Figure It Out” is Neglective

I once had a boss who didn’t know how her employees ran her business, so she had a “figure it out” demeanor when it came to training new hires. As a new hire, I was in a perpetual state of stress and anxiety, terrified I’d royally mess something up.

I unfortunately have now become this boss to myself. I tell myself to “figure it out” all the time and throw myself into stressful situations when I don’t have to.

“Figure it out” is a neglective way to train a new employee and it’s a neglective way to treat yourself while running a business. Ask for help, hire experts, and join support groups who have already figured out what you need.

Clocking Out Early Is Encouraged

The same boss didn’t like it when her employees left the office before 7PM and didn’t clock in 10 hours. I worked hard at that job and found this unspoken expectation absurd, so on the days I wanted to leave at 5PM my co-worker and I would stand watch for each other and run past her line of sight so that she wouldn’t see us leave.

Today, I get annoyed at myself if I clock out before 5PM — I feel guilty that I didn’t do more that day. I remind myself that I’m here on this earth to live, not work.

I remind myself that when this expectation was set on me by someone else, it felt absurd. Clocking out early is strongly preferred and I should continue to strive for that.

Work Should Be Inspiring

When I’ve hit a wall at past jobs, it has been because the business lost its initial glimmer and I hadn’t received a second dose of inspiration to keep going.

This injection of inspiration has been long overdue for me at my business. No wonder I’ve felt burnt out, I’ve been seriously slacking in motivating and inspiring my #1 employee — myself.

Creativity around merging my work with what I’m currently passionate about outside of work has been one way I’ve been bringing more fire to my business. Work shouldn’t just be a means to paycheck, it should also be a source of inspiration and meaning.

I write thoughtful, personal Friday morning emails called The Crux to help entrepreneurs turn their startup chase into a victory lap. Join here to get my best musings in your inbox.

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Sophia Sunwoo

I create moneymaking brands with womxn entrepreneurs who refuse to settle for mediocre. www.ascent-strategy.com