Year One: 9 Smart Moves + 10 Rookie Mistakes
By Jim Thompson / BrightTrail.biz
The second craziest thing I’ve done in my life was in 2004.
I hopped a plane to St. Louis with no hotel and no game plan. I handed my last $400 to a scalper — aka The Chicken Man — in an alley for a ticket that looked fresh off an HP Deskjet.
But the ticket wasn’t fake.
The Chicken Man came through.
And I saw my beloved Red Sox win their first World Series since 1918.
Sometimes you just have to believe.
Now, the craziest thing I ever did?
That was one year ago. I left a pretty good gig on Madison Avenue with a successful media publisher to start my own personal branding agency.
It wasn’t The Chicken Man this time — it was my wife, Jen. She backed me every step, even the ones that tightened our monthly budget so I could test drive a dream of telling people’s stories my own way.
I learned a lot in Year One.
So if you’re launching a project that scares, challenges, and or excites you, these could be helpful.
Year One: What I’d Do Again
Prepare: Website, LLC, bank account, logo, payment processing — the scaffolding matters.
Prospect: Your first job isn’t to land clients; it’s to learn what’s holding them back. Join the rooms where they gather and listen.
Mentor: SCORE connected me to wisdom that shaved years off the learning curve. I have the best in Stellario D'Urso. And I still can’t believe his advice is free.
CRM: It’s not optional you need one. I chose High Level — affordable, complete, and worth the learning curve. (Full disclosure: if you sign up through this link, I get a small referral credit.)
Learn: Read the top three books in your niche. Then go back and read them again. My favorites: Atomic Habits (James Clear), Building a StoryBrand (Donald Miller), The Four-Hour Workweek (Tim Ferriss), Influence (Robert Cialdini).
Think Long: Assume 18 months before real traction. Save up a runway or line up clients to survive that stretch. Even better, do both.
Know Who You Help: Be able to describe your ideal client in one clean sentence.
Know Your Value: Define exactly what problem you solve and why you’re qualified to do it.
Lock in Testimonials: Don’t be afraid to ask your first happy clients for testimonials and referrals.
Year One: What I’d Do Differently
Website: Start simple. A single-screen landing page beats six months of perfectionism.
Logo: Obsess less, hire a professional (h/t Stephanie Apessos).
Social: Fewer platforms, more consistency.
Tools: Rent monthly until you know you’ll actually use them.
Prioritize and Sequence: Do what’s important first in the order they are needed. Don’t focus only on the parts you enjoy.
Pitch: Have your answer to “What do you do?” ready and memorized. Adjust it if blank stares persist.
Business Cards: Yes, they still matter.
Vendor Partners: Build those relationships early. Yes you’re paying them, but you’ll need them.
Your Network: Don’t ask for business — ask for introductions.
Plan, Prep, Go: Waiting two years was too long. Yes I was preparing, but I was also procrastinating.
The Takeaway
Starting Bright Trail was the craziest thing I’ve done.
And the best.
Because in a world full of noise, people need experts they can trust.
They buy why you care first.
They buy the story that proves it next.
And if Year One taught me anything, it's this:
Sometimes you just have to believe.
Now if you need a little professional help growing your customer base or building your personal media brand, let's talk. Just reserve a 30-minute chat. I promise it's a free, no-judgment-zone experience.
Pathfinder is written by Bright Trail founder Jim Thompson who's grown digital audiences for some of America's top media brands including Fox Interactive, Billboard, Hollywood Reporter, Modern Luxury and Gary Vaynerchuk's personal brand.
