24 Short Lessons from 24 Months of No More Bosses

For many, quitting a well-paying corporate job in their 40s to pursue self-employment is nuts. Well, call me crazy then.

Although largely unintentional, I left corporate two years ago to head back to the pathless path of entrepreneurship.

Unintentional because it never crossed my mind then. Even though I had five businesses under my belt, I also know the tolls it exert on one. I don’t have that stamina anymore.

But an argument at work made me throw the letter (or rather email). Still, that wasn’t the final straw. I was still adamant about remaining in corporate. But that came when an interviewer remarked that he was concerned about my influencer status.

I did not bother rebutting. I smiled and wished the meeting could end soon.

Even though the private sector might be better than the quasi-government entity I was with, it still seems like trading one kind of bull shit for another.

I withdrew from all other job interviews and decided to take another leap into the uncertainty abyss.

And it has been almost 24 months since.

Has it been all rainbows and butterflies? Hell no. I’ve faced numerous challenges and obstacles over the past 24 months as a solopreneur. 

But I can honestly say I have never felt more alive.

Fast forward to today, I:

• Work 30 hours a week with two HR tech clients on retainer.
• Co-host Work It by CNA.
• Ad hoc commissioned work as writer, speaker, moderator and/or influencer.
• Working from home, I wake at 9:00am (after my post-school run morning nap) and start work from 9:30am. Work ends at 4:30pm
• have an online-demand course on how I scale LinkedIn
• Multiple sources of income.

While everyone’s path is different, I hope these bite-sized takeaways resonate with kindred spirits bitten by the entrepreneurial bug who feel unfulfilled chasing someone else’s definition of success.

There were many sleepless nights filled with doubt, but deep down, I knew…

I was meant to do this. To create my version of work-life balance and financial freedom. And know what? You probably can, too.

So brew a cup of coffee (or pour a glass of wine) and soak up these 24 lessons from my first 24 months of self-employment:

1. Validate demand before you build – it reduces risk. Sell before you create. I “sold” before I even incorporated my business entity.
2. Be ruthless with time management and work discipline. They are your competitive edge.
3. Because you don’t like to work 40 hours for others, it does not mean you need to work 100 hours for yourself. 
4. Lifestyle business is achievable even in an expensive city.
5. Make peace with huge fluctuations. Unlike stock prices, they do not reduce your worth by one bit.
6. There is never a perfect plan. Often you just have to take a leap and build the parachute on the way down.
7. Solopreneurship is lonely. Find your tribe of people to walk together.
8. Leverage your superpower (i.e. past experience and skills) – it makes the transition smoother.
9. Not everyone may understand your path. Stay humble and focus on your own journey.
10. Appreciate others’ work and build genuine relationships – screw networking.
11. Perseverance and grit can help you overcome challenging circumstances. Persist even when things seem bleak.
12. Trust your gut instincts until proven wrong.
13. Celebrate small wins.
14. Failures and setbacks as opportunities to learn and improve. (Refer to the Beckham documentary I mentioned below)
15. Avoid comparing yourself to carefully curated social media highlights of others. Focus on your own definitions of success.
16. Know what are shiny new objects to you and shut them out of your work life.
17. Surround yourself with people who uplift and believe in you during periods of self-doubt.
18. Sometimes all you need is a change of work environment. Cafes work well for me.
19. A good pair of Active Noise Cancellation headphones is a great investment. Check out Poly Surround V80.
20. Make time for learning. Schedule them into your calendar.
21. Technology is the next best thing to cloning yourself.
22. A bad day does not equate to a bad career choice.
23. Unless you need publicity, remember that publicity does not pay bills.
24. Recurring revenue provides stability alongside client work.

I hope these bite-sized takeaways resonate with others bitten by the entrepreneurial bug.

While everyone’s path is different, you can create work-life balance and financial freedom on your own terms.

Brew some coffee and soak up these lessons from my first 24 months of self-employment.

What’s holding you back from taking the leap?