Having a clear goal is only the beginning of a dream. The real challenge is sticking with it especially when motivation runs low and life gets in the way.
But what if the missing piece isn’t hustle or talent, but a simple tool that gives your goal structure, direction, and momentum? I learned this the hard way.
The journey to self-empowerment rarely goes smoothly the first time around. Back in the mid-2000s, I threw myself headfirst into the deep end of creative entrepreneurship and I sank.

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The First Leap: Quitting Without a Plan
At the time, I was on my third job in two years. I lasted six months before my creative instincts started howling for attention.
One morning, I woke up, decided I’d had enough of 9 to 5 corporate dictatorships, and quit. No plan. No warning.
I was ready to follow my passion and write the novel I’d been procrastinating for months.
I gave a big speech to my family about “living my dreams” and “not wasting my youth.” They thought I was completely unhinged.
And looking back? They weren’t wrong.
The Harsh Reality of Dream-Chasing
I had no bills, thanks to living at home, no financial responsibilities beyond a phone plan and still managed to run out of money within two months.
Yes, I did finish that novel. But I also ran out of printer ink, phone credit, petrol and money for wifi. I asked my dad for cash. He said no. And rightly so.
I stretched things for another month by siphoning petrol from the family car and “borrowing” my mum’s phone credits.
Eventually, I went job hunting. It took three painful months to find a job. My parents were furious. I was defeated.
I hadn’t failed because I lacked talent. I failed because I had no plan.
The 4 Big Mistakes That Killed My First Dream
1. I Had No Clear Action Plan
I quit on impulse without a strategy. My only “goal” was to finish the book. I had no steps in place for what came after that.
2. I Had No Back-Up Plan
There was zero consideration for what I’d do if things didn’t go smoothly. Blind faith is not a strategy. It’s a gamble.
3. I Had No Financial Cushion
Even with no rent or major bills, I ran out of money fast. I hadn’t budgeted, saved, or figured out how I’d sustain myself long enough to see results.
4. I Was Naively Overconfident
I believed once the book was done, everything would magically fall into place. It was the kind of belief only a youngster without a mortgage could afford.
What I Learned the Hard Way
You can’t just leap and hope the net will appear. That kind of thinking leads to burnout, resentment, and broken dreams.
What you need instead is a clear plan, financial awareness, and a mindset that embraces structure over chaos.
Following your passion is not the hard part. Staying consistent when reality gets tough? That’s where most people drop off. But it doesn’t have to be that way.
The Second Attempt: What I Did Differently
Fast-forward to years later, and I gave my dream another go. Only this time, I had:-
- A 4-year plan I’d been working on in the background.
- A financial runway to support myself.
- A strategy to grow my writing business step by step.
It’s turned out to be the most fulfilling experience of my life. Failure didn’t mean I wasn’t meant to do this. It meant I had to do it differently.
Don’t Just Dream. You Need to Build a Roadmap
If you’re a solopreneur, freelancer, or dreamer with a vision, take it from me: dreams without plans are just expensive hobbies.
Want to get started the right way? Check out A Guide to Getting Started with a Plan.
Tips, tools and best practices for turning your dream into a goal and your goal into results.
Anna is a solopreneur, writer, and creative entrepreneur who left her 9–5 after paying off over $40,000 in debt to pursue a more intentional life. She founded The Writer Entrepreneur to empower others to build debt-free, freedom-driven lives through smart planning, goal-setting, and online income streams. She has been featured on HuffPost, YouQueen & Fitnancials among others. Learn more about Anna HERE.
This post may contain affiliate links which means I will make a small commission if you purchase through those links. Read full disclosure HERE.