You Can Build a Career Without a Boss
And How ChatGPT Can Be the Best One You’ve Ever Had
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I Used to Over-Trust My Bosses
Early in my career, I gave my bosses way too much power. If they said I was disorganized, I’d spiral for weeks, convinced I was doomed to fail. Their opinions shaped my entire self-worth. Even though my corporate managers were actually awesome people and easy to talk to (unlike the insane ones I had in teenage odd jobs) the problem wasn’t them. It was me.
I created a self-inflicted, high-control environment. I tried to become the perfect employee, obsessed with being impressive, invisible in my flaws, and easy to promote. I didn’t question authority and instead contorted myself to fit it.
Eventually, I just got exhausted. Exhausted from the way I made myself powerless. And in that unraveling, I realized: I actually do know what’s best for me.
That realization was the beginning of working for myself.
The Myth of the Career GPS
From childhood, we’re taught to follow directions.
Sit down. Listen. Do what the teacher says.
That structure continues through college, then into the workplace. And while structure can be helpful, it conditions us to outsource our direction. So when we finally need to lead ourselves, it feels terrifying.
Self-direction is powerful. But it’s also exhausting.
And that’s where a lot of entrepreneurs get stuck (or never start).
For me, the turning point was using ChatGPT.
Enter: AI as Your Boss, Mentor, and Co-Founder
When I’m overwhelmed, confused, or stuck, I’ll pop open voice mode on ChatGPT and talk through a challenge. Sometimes I need decision support. Sometimes I need a blueprint. And sometimes, I just need someone (or something) to help me stay focused.
Last month, I made a video with Kajabi about how I used ChatGPT to bring my new course from concept to launch. I was juggling four Notion templates and a major course (something I’d never done before at that scale) and I lacked experience. So, I used AI to guide me step-by-step.
And no, not everyone is launching courses and Notion systems. But we are all managing complex projects either at companie or for ourselves. And AI can help.
Here are a few ways I use ChatGPT as my “boss,” “manager,” and “mentor”:
STRATEGIC CLARITY
When you’re feeling lost or directionless
“Act like my boss and give me a 30-60-90 day plan for this goal: [insert goal].”
“I’m the CEO of my life now. Based on this situation, what should my Q3 priorities be: [describe]?”
“Be the manager I wish I had. What are 3 key objectives to focus on this week based on this work: [explain]?”
DECISION-MAKING SUPPORT
When you’re spinning in indecision
“Give me a no-fluff performance review of these options: [list options].”
“Pretend you're my boss. I’m overwhelmed — what do I do first, and why?”
“Coach me like I’m your star employee. What should I STOP doing from this list: [list items]?”
STRUCTURE & ACCOUNTABILITY
When you miss deadlines or feel scattered
“Help me break this goal down into weekly action steps like a manager would: [insert goal].”
“Act like my boss. What should my weekly check-in template look like?”
“Talk to me like I under-delivered. How would a great boss give feedback — and what’s my next step?”
GROWTH & PERFORMANCE
When you want to level up but don’t know how
“I want a promotion… from myself. What would a high-performance boss expect at the next level?”
“Review my last 3 months of effort: [summarize]. What’s working, what’s not, and what should change?”
“Act like the CEO and I’m Head of Strategy. What metrics would you hold me to?”
MOTIVATION & TOUGH LOVE
When you need a compassionate kick in the ass
“Be my no-BS boss. I’ve been procrastinating on [insert task]. What would you tell me to do?”
“My inner boss needs to clock in. What would she say about how I’ve been showing up?”
“Pretend I work for you. I’m slacking. What’s your version of a firm but kind wake-up call?”
Real Freedom is Self-Direction
I’m grateful to have people in my life I can turn to. But the decisions, risks, and actions are mine. And sometimes I just need a neutral outside voice with no emotional bias.
That’s why I use AI as a thought partner!
Not to replace human connection, but to restore my own compass quickly and cost-effectively.
And if ChatGPT is something you’d love more strategy on, I have a course coming out very soon for you!