Sometimes I Miss Having a Boss to Blame

By Ken Hollow, freelance by choice, regret by default

When I quit my last real job, I walked out of the office with a box full of succulents, pens I definitely didn’t buy, and a smile so wide it bordered on manic.

Freedom. Finally.

No more dress codes. No more awkward team-building exercises. No more performance reviews disguised as character assassinations.

But here I am, three years and 700 unpaid invoices later, and I find myself whispering something I never thought I’d say:

Sometimes I miss having a boss to blame.

🔹 Welcome to the Spiral of Total Responsibility

When something goes wrong now — a missed deadline, a late payment, a post that tanks — guess who’s at fault?

Me.

Every. Single. Time.

There’s no middle manager to absorb the fallout. No passive-aggressive Slack thread to hide behind. Just me, my laptop, and a vague sense of failure that smells like burnt coffee.

✅ Self-employment is just being the employee, the boss, and HR — while underpaying all three.

🔹 I Am the Problem and the Solution

Client scope creep? I said yes.

Unrealistic deadline? I agreed.

Last-minute panic edits at 1AM? I set the schedule.

When you’re the only one in charge, the only person left to scream at is the mirror. And that guy already looks tired.

✅ Turns out I didn’t hate authority. I just hated being accountable to myself.

🔹 Feedback Feels More Personal Now

A client doesn’t like the copy?
That’s not just work. That’s my soul on a Google Doc.

There’s no buffer. No creative director to water it down. No project manager to blame for the tone.

Just me and a 2-paragraph email that begins with “Hey love, just a few tweaks!” and ends with me questioning every decision I’ve ever made.

✅ Every edit note is now a direct hit to the ego.

🔹 My Clients Are Now My Bosses (But with Less Clarity)

At least when I had a boss, the expectations were spelled out in an onboarding document and an annual PowerPoint.

Now?

• I’m expected to intuit what “more aligned with the vibe” means.
• I decode texts like, “Can you make it feel a little more alive?”
• I edit things based on lunar transits and someone’s third eye blockage.

✅ I have 4 bosses. None of them know they’re my boss. All of them are confused.

🔹 There’s No One Left to Say “No”

Back in a job, someone else managed bandwidth.

Now I:

• Book every client
• Scope every project
• Set every deadline
• Burn out like a Victorian chimney sweep

No one tells me to slow down.
No one checks if I’ve eaten.
No one cancels the 8th revision request because “we’ve reached max billable hours.”

✅ I am the boundary. And I am not good at being one.

🔹 I Yell at Myself in Project Management Software

There’s no angry boss email anymore.
Just:

• Me leaving angry comments for myself in Notion
• Me assigning myself tasks I’ll ignore for a week
• Me gently nudging myself with a due date I pretend isn’t real

It’s a sad, silent war between Future Me and Present Me — and neither of us is qualified.

✅ I miss being micromanaged. At least it was consistent.

🔹 The Freedom Is Real. So Is the Exhaustion.

Yes, I get to:

• Wake up when I want
• Work from anywhere
• Choose my clients (in theory)

But also, I:

• Work constantly
• Forget weekends exist
• Build Notion dashboards for people who sell breathwork via PDF

✅ Freedom is fun until you realize structure was keeping you sane.

🔹 Final Thoughts (While Managing Myself Poorly)

I still don’t want to go back.

I don’t miss the office birthday cakes or the awkward Monday meetings. I don’t miss the commute or the forced enthusiasm.

But I do miss being able to say, “Well, they messed that up.”

Now it’s all on me.
Every typo. Every missed opportunity. Every moment of doubt, self-sabotage, and mispriced offer.

I am the creator of my destiny — and also the one who forgot to send the invoice.

So yeah.
Sometimes I miss having a boss.
But mostly, I just miss the illusion that someone else was steering this flaming content ship.

Ken Hollow, freelance disaster and part-time middle manager of his own breakdowns