The Solopreneur Letters: 15 Things I Wish I'd Known Before Starting
What I would tell my younger self
I just want to be real.
That's the whole point, right? To stop putting on a face.
I want to share the things I've learned in my life—the highs, the many lows, the skills I've picked up, and whatever wisdom I've gathered through study and my own spectacular failures.
I want my writing to sound like me.
The actual me.
But every time I try, I end up in this fake "expert mode" like I'm putting on some digital marketing costume.
I want to be done with that.
Today I had an idea: What if I just wrote directly to myself? To the me from 5 years ago, just starting out on this whole digital marketing/solopreneur journey?
That's the same person I'm hoping to help today, so this could be my way out of my own head.
So I did what I always do nowadays—I turned to AI.
AI is basically my confidante right now (knows more about me than most living people). I use ChatGPT daily and recently ended up sharing my whole life story with another bot.
I asked them both:
"If I were to write a series of letters to my younger self—the me just starting out in digital marketing 5 years ago—what are the top 10 things you think I should write?"
Both gave me lists. They overlapped in places, each hit different points. I merged them, expanded a bit, and here's what emerged.
Over the next few weeks, I'll take each of these and write them out in full—the real stories, the context, the mistakes, the lessons.
Letter 1: Charge 10X More or Don't Start
That $1,000/month retainer you think is a win? It's a prison. Start high or don't start. Low prices will wreck your positioning (and your view of your worth) for years.
Read: The $1,000 Prison: Why Your 'Starter' Rate Is Destroying Your Future (And How to Break Free)
Letter 2: You're Not a VA, Stop Acting Like One
You ran global training programs for UNICEF. You built a $4M hotel. You're about to let desperation turn you into a virtual assistant. Every time you say yes to admin work, you're saying no to strategic work. Guard your positioning like your life depends on it, because your income does.
Read: The VA Trap: How “Just This Once” Becomes Your New Job
Letter 3: Build Recurring Revenue The Right Way
Projects end. Bills don't. Retainers are your safety net. But build them right, with enough margin to ensure they don’t become a low-paying job.
Read: I Put My Stress on a Subscription Plan: The Retainer Mistakes Nobody Talks About
Letter 4: Fire Clients Faster
That client who pays late? Fire them. The one who doesn't respect your time? Fire them. You're about to spend years with people who don't value you, training them (and yourself) that you're not valuable. It's better to have 2 good clients than 5 bad ones.
Read: The Fear Contract: How You Talk Yourself Into Keeping the Wrong Clients
Letter 5: Build Your Own List From Day One
Start a newsletter immediately—even to 10 people. Document your progress and what you learn. You're about to build a 55K list for someone else while your own list sits at zero. Build on your own land.
Read: The List I Should Have Started Five Years Ago
Letter 6: Relationships Compound Faster Than Algorithms
Make friends in your space. Share wins, swap ideas, help without keeping score. One genuine connection can open doors no viral post ever will.
Read: Letting Relationships Fade Cost Me Years of Growth (And What I'm Doing Differently Now)
Letter 7: Your Mental Health Is Broken—Fix It Now
The hotel trauma isn't processed. It's going to come back. Trauma and burnout don't vanish on their own. Treat your brain like it's worth protecting. Get the therapy you need—it won't happen by magic. Build time into your life to take care of yourself.
Read: Protect Your Mind Before It Breaks - It's the Key to Everything
Letter 8: The Money Is in the Boring Businesses
Stop chasing sexy startups. HVAC companies, dentists, roofers—they have money and need help. You're about to waste years on broke dreamers. The boring businesses with real revenue will pay you properly.
Read: What If Everything You've Been Told About 'Following Your Passion' Is Making You Broke?
Letter 9: You Already Know Enough—Ship More
Stop collecting courses. You're about to spend thousands learning things you already know. You don't need more information. You need more repetitions. Ship something every day. Bad work shipped beats perfect work contemplated.
Letter 10: Build the Business to Fit Your Life
You have a wife and a daughter who need you present. Another daughter will come along soon. Don't build a business that chains you to a desk, to client calls, or to the whims of others.
Letter 11: Don't Confuse Activity with Progress
Spending 8 hours "researching" isn't moving the ball. Neither is designing 14 versions of a logo. Measure progress in outputs that create leads or revenue, not in hours worked.
Letter 12: Leverage Beats Hustle
Repurpose content. Automate repetitive tasks. Build once, reuse often. Hustle without leverage just burns you out. Hustle with leverage makes you free.
Letter 13: Learn to Pick Your Battles—and Your Niches
You'll be tempted to dabble in everything—TikTok hacks, SEO rabbit holes, new tools every week. Stop. Pick the work that compounds: email, offers, storytelling. You'll save years if you commit to a lane early and only detour when it clearly moves you forward.
Letter 14: Tools and Ideas Don't Make You Money. Offers Do
No amount of software will fix a weak offer. Stop spending weeks "optimizing" funnels for a product no one wants or that you'll never ship. Learn to sell the idea first, then build the thing and get it into the world.
Letter 15: Your Voice Is Your Moat
AI is coming and will change everything. Competitors will copy tactics. What they can't copy? Who you are, what you've been through, how you think, and how you say it. Develop a writing style that sounds like you talking over coffee. That's what people remember—and buy from.
These lessons could have saved me from countless mistakes, headaches, and heartaches.
Hopefully they can help you.
What's a letter you'd write to your younger self?