From Resignation Letters to Resilience: My Bumpy Road to Self-Employment

Key Phrase: Bumpy Road to Self-Employment

Earlier today, I read a post by a former civil servant who once imagined that quitting her job would usher in stylish freedom—complete with a sleek office, confident attitude, and flexible schedules. But what she discovered instead was a truly bumpy road to self-employment, filled with more tears than tea breaks.

Her story reminded me so much of my own.

More than ten years ago, I quit my demanding microfinance job, fired up by motivational books like Rich Dad, Poor Dad and Awaken the Giant Within. In hindsight, I probably didn’t fully grasp what those books meant. But the message I clung to was clear: failure can be your biggest turning point.

What I didn’t know then is that the road ahead would be anything but smooth.


A Decision That Changed Everything

I still remember the first resignation letter I wrote. I sent it to my branch manager — and she talked me out of it. The second time, I didn’t consult anyone. I had already started a small grocery business and hired a young man to sell for me. When I finally resigned, I took over full-time at the grocery.

The dream? Independence.
The reality? Customers ghosting me. Rotten supplies. Long, lonely hours.

I got bored, frustrated, and soon — broke. It wasn’t long before I started job hunting again. The role I got paid so little, it stings even now to recall. I eventually bounced through a few other unstable jobs, never quite finding the security or satisfaction I needed.


Back to the Hustle: A New Chapter, Same Challenges

I returned to business — again selling groceries — now with a one-year-old baby to care for. It was survival by wit. Rent piled up. Stock moved slowly. And once more, I was forced to close shop and start over.

After months of struggling, I finally landed a job and decided to run a side hustle alongside. This time it was egg wholesale, and I found a helpful young woman to manage sales. Things looked up — until she left for college just three months in.

Now I was working full-time, mothering, and selling eggs. Because my home, business, and job were in close proximity, I made it work — barely. I’d take orders in the evenings and deliver when I could.

💡 Hard lesson: The biggest challenge wasn’t the workload. It was separating business money from personal money. That thin line blurred constantly.

📘 Affiliate link: Cash Book for Small Businesses on Amazon
📗 Affiliate link: Budget Planner for Hustlers
📙 Affiliate link: Egg Business Success Guide


Motherhood and Hustling: The Untold Weight

Being a motherpreneur isn’t just a job. It’s a balancing act on a tightrope with no safety net. Between diapers, delivery runs, unpaid debts, and unending restocks, the pressure was unmatched.

Eventually, I found myself jobless again — this time with two children, more responsibilities, and debts I couldn’t ignore. I had to return home and rebuild from scratch. Again.

But now I had something I didn’t have before: endurance.

Support Is Not a Weakness

In this phase of my life, one truth has become crystal clear: The support of others cannot be understated. From that helpful egg seller to relatives who watched my kids, and even friends who sent customers my way — this road would’ve been impossible alone.

If you’re on this journey, I urge you to seek out support — whether it’s mentorship, partnerships, or just people to encourage you. The myth of the solo superwoman is just that — a myth.

🧭 Outbound resource: Motherpreneur Kenya Facebook Group

Updated Resource: Why Most Small Businesses Fail in the First 3 Years

Small businesses often struggle to survive beyond their first few years. A recent study highlights key pitfalls:

These findings apply directly to my journey: I underestimated working capital, mixed business with personal finances, and didn’t have a marketing or growth strategy aligned with my reality.


External Reads

  • Practical guide on why businesses often fold within their first 3–5 years 1stformations.co.uk

Blogging, Deras, and Cleaning — Starting Again

Today, I’m in business again. Selling deras, sharing my story through my blog Lobby Reflections, and laying the foundation to start a home cleaning and laundry service.

I may not have it all figured out, but I’ve learned to appreciate the process. I no longer chase success in leaps — I show up consistently, brick by brick.

Read more on my blog:

Selling Deras in Kenya

The Gift of Becoming

What the Bumpy Road to Self-Employment Has Taught Me

Lessons I’ve Learned on the Bumpy Road to Self-Employment

1. Dreaming Is Free — Building Is Costly

It’s easy to dream of entrepreneurship when you’re seated behind a desk. The cost — emotional, financial, physical — reveals itself only after you’ve stepped out.

2. Resilience Is Built, Not Borrowed

No book, quote, or mentor can hand you resilience. You build it through experience, failure, and getting back up… repeatedly.

3. Business ≠ Freedom Unless You Plan It

Many of us leave employment hoping for freedom. But without structure and boundaries, business becomes another form of slavery.

4. Support Systems Are Your Lifeline

From caregivers to friends to suppliers, business becomes manageable when you are not doing it all alone. Asking for help is not weakness — it’s wisdom.


Final Thoughts: Your Story Is Still Unfolding

If you’re navigating your own bumpy road to self-employment, I hope my journey shows you that falling down doesn’t mean failure. What matters is getting back up — wiser, stronger, and a little more determined each time.

You’re allowed to rest. To ask for help. To restart. What you’re not allowed to do? Give up.

Let’s keep walking this road — even when it gets bumpy.


💬 I’d love to hear from you:

What has your self-employment journey looked like so far? Are you a motherpreneur, side hustler, or someone rebuilding from scratch like me?

👇 Share your thoughts in the comments or message me on:
📍 Facebook Page
📍 LinkedIn

🧺 Check out my latest blog posts and deras: www.lobbyreflections.co.ke

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