Most people start a business for freedom—freedom from:
- Bosses/Micromanagement
- Schedules/Lack of flexibility
- Income Ceilings
- Meaningless Work/Misalignment
- Policies and Bureaucracy
And who can blame us?
So off we go, building our own businesses to escape the five usual suspects—but then something awful happens.
- We become bad bosses. We drive ourselves relentlessly, never give ourselves a day off, and constantly criticize our work… demanding improvement.
- Then we work 7 days a week often for 10-12 hours a day.
- And we’re so worried about cash flow that we barely pay ourselves. Trying to keep enough in the business account so as to not go broke.
- Then we find ourselves doing EVERY job that needs doing, no matter if we’re proficient in that area or not.
- Finally, we start to unconsciously apply silly rules and restrictions to ourselves in hopes of keeping the business afloat. An example might be feeling like we need to be available to all clients 24/7 if they need anything.
And before you know it, we have undone the very reasons we became entrepreneurs in the first place. Yet, somehow it’s slightly more tolerable because we’re doing it to ourselves. 🤷🏼♂️
So what can we do about it? How can we treat ourselves better, create more scheduling flexibility, make more money doing work we care about, and kill every stupid policy we’ve imposed on ourselves?
My honest answer? Slowly, over time, and with a little hand wringing. Sorry!
Most of the above problems that we’re trying to escape when we leave the corporate world and then recreate for ourselves as business owners materialize due to fear.
- Fear we’re not talented enough.
- Fear the phone won’t ring.
- Fear this idea won’t work.
- Fear that if we don’t over-deliver at all times, we’ll go broke.
There are lots of ways we can work with fear, but it has been my experience (and that of my clients) that working through these fears takes time.
- First, we have to develop enough self-awareness so we can start to detect fear in real time.
- Then we have to understand that what our mind is telling us (the worst-case scenario) is not true. It’s just the mind making shit up. So we have to choose not to believe it.
- Then we have to make the decision to act contrary to that fear.
Developing a strong sense of self-awareness, catching the fear in real-time, and intentionally making decisions to act contrary are all skills that need to be honed over time.
Micro-practice for this week (5–10 minutes)
- Boss Audit: Write one sentence: If a boss treated me like I treat myself, would I quit? Why?
- Kill One Policy: Pick one dumb rule you’re imposing (e.g., “reply instantly 24/7”). Cross it out. Replace it with a sane rule (e.g., “reply within business hours; urgent clients have a hotline”). Test for 7 days.
- Pay Yourself First: Move a fixed % to personal pay this Friday—even if small. Protect it.
- One Job Off Your Plate: Delegate, defer, or delete one task you’re bad at (or hate).
Do this for a week and see how your work (and nervous system) responds.
Freedom isn’t a vibe. It’s a set of practiced choices.
If you try the micro-practice, hit reply and tell me which policy you killed. I read and reply to ALL emails.