When you’re thinking about your life and your career, I suggest you pause and ask yourself a few key questions.
The Short Version
If you prefer straight to the point, here are the cliff notes. If you’re looking for the how-to, skip to Part II. But whether you’re already in business or just thinking about it, take the time to read this first.
80% of businesses fail in the first five years. When I asked my mentor Tom why, he said most people get distracted by life and fail to consistently focus on what actually moves the needle. Sometimes it’s because those things are uncomfortable. Sometimes it’s because they don’t have a mentor. But in his experience, it’s usually because they didn’t have a big enough why. I’ve personally had to shut down a business—I get it.
Being in business is phenomenal. No sugar-coating. I’m in it for the freedom, the choices, the impact, and yes, the income. But to make it work, you’ll probably have to do things you don’t enjoy. You’ll definitely have to change. And you’ll need a reason bigger than just having fun or liking what you do—because when things get tough, that why is what will carry you through. So before you start, ask yourself: Why?
(We’ll go over the ABCs of getting your business running in Part II.)
Oh, and if you’d rather read this in Polish—you’re in luck. Thanks to Witold Rugowski, this article has been translated.
A Question: Why?
I asked my dad a tough question when I was 25:
“Now that my sister and I are adults and you see who we’ve become, what would you have done differently raising us?”
He paused for a long moment and finally answered,
“I would’ve taught you to dream beyond college. We pushed college hard, thinking you’d figure out the rest on your own. But we didn’t help you prepare for what came after.”
It wasn’t what I expected, but I knew exactly what he meant.
I went through five different majors in college—not because I struggled (I was a 4.0 student), but because I had no idea what I wanted out of life. My sister had panic attacks leading up to graduation. We had the drive and skills… but no vision. No dream. No why.
So I ask you now: What’s your why?
And not just “why do you want to be a business owner?”
One of my early mentors took me to a conference where I heard Mark Victor Hansen (the Chicken Soup for the Soul guy) say something that stuck:
“Most people go to school, get a job, earn some money and time, and then try to carve out whatever life they can. The problem is, that’s backwards. Truly successful people start with the life they want. They ask themselves what they want to do, have, and become. Then they find someone who’s living that life, ask how they got there, and—if it’s legal, moral, and ethical—follow their lead.”
I remember asking Tom afterward,
“What if the path is selling toothbrushes or shoveling shit?”
He laughed and said,
“If shoveling shit got you everything you wanted out of life, wouldn’t you be happy?”
He had a point.
There will always be parts of the work you don’t like. Olympic athletes don’t love every training session. Nurses don’t love cleaning bedpans. The real question is: What do you want out of life—and are you moving toward it?
If you don’t know, start by writing it down like we did. I found it hard. My wife Julie, on the other hand, fired off 140 items in one sitting. She’s an amazing visionary. I got to about 20—surf more, travel more—before I showed Tom. He looked and said, “Needs more detail. Dreams need detail.”
So I started over.
Now my list has over 100 things on it—and the wild part? I keep crossing them off. I know I’m living a life of purpose. (You’ll find my list at the end of this post.)
The Dream
Most mornings, I wake up when I want. I surf. I meet amazing people. Julie and I go for midday swims. I work from coffee shops. I face incredible challenges, serve Fortune 500 clients, and make a solid living—far more than we ever could as employees. And we work from home.
It’s about freedom, choice, making an impact, and generating income. Simple as that.
Is it right for you? I can’t say. For that freedom, we trade stability. Some day, maybe that comes too—but nothing is guaranteed. Even big companies don’t offer the certainty they once did.
It takes serious focus, a willingness to learn, to change, to do hard things, and a strong work ethic.
Can it be done? Absolutely. We’re living proof—and so are many others.
What Made Me Choose This Path?
Back then, I was a part-time teacher and programmer who had bounced around jobs. Truthfully? I was a mediocre employee. I didn’t like being told what to do. But I loved surfing, connecting with people, building things, and most of all—freedom.
So when I met Quinn McLaughlin, the timing was perfect.
He was sitting at Lulu’s, typing on the smallest laptop I’d ever seen. We geeked out over tech stuff. He had just closed his video game company, Osiris, and was living life on his terms—kiting or biking daily, working from coffee shops or the beach. He made enough to live comfortably in Santa Cruz (no small feat) and still traveled for months at a time. He was living my dream.
I pestered him until he gave me a shot. He introduced me to my first client and lent me his credibility. I’m still grateful.
Then I met Tom, who taught me that being a contractor meant owning a business—not just being a freelancer without benefits. He and his wife had built multiple businesses—some big, some small—and developed systems that allowed them to step away and still have the business run.
In short, they were free. And they showed me that business can be a path to freedom, impact, and financial security. That vision is what drives Julie and me today. We want others to come play with us.
The What
On my first day with Tom, we talked about how to evaluate a business opportunity. Three ideas stuck with me—and I still use them today:
- “Your income will match the size of the problems you solve.”
Big problems = big income. That’s why heart surgeons earn more than stock clerks. Ask yourself: What problem does this business solve? - “Timing is everything.”
Smart entrepreneurs see trends and act early. Ask: Will more people need this next year than this year? - “Find someone who’s succeeded and has a vested interest in helping you win.”
Nothing beats having a mentor who’s truly in your corner.
I could write books about each of these. (Maybe I will someday.)
If you already know what you love—go do it. If you’re still searching, look for something that keeps you up at night because you’re so excited. Then figure out how to turn that into a business.
What do we do? We solve problems. Sure, Peter and I play with computers, but that’s just how. The real heart of what we do is about impact.
Bonus: My Top 100 Things I Want to Have, Do & Become
I made this list the same year I started my business. We’ve achieved many—and still have a long way to go. I’m sharing it because Julie’s list inspired me to stretch, and maybe this will do the same for you.
The Top 100 Things I Want to Have, Do & Become
I wrote this list the same year I started my business. We’ve accomplished a number of these and have quite a way to go on others. Every time I see this I still get emotional. I’m sharing it because seeing Julie’s list inspired me to stretch to make my own. Sometimes you need to see someone else do it for inspiration.
- Julie has the option to be a stay at home mom
- Julie gets her PhD
- Buy a house
- 5br / 4ba home on the ocean overlooking good surf, with palm trees, mediterranean style, outdoor shower & hot tub.
- Honeymoon on a warm tropical location
- Buying Julie’s wedding present cash
- Get completely barreled in an aqua-marine hollow reef wave
- Time to read fun books
- Own 12 properties
- Camping in Baja on a good south with close friends
- High Proformance 9′0 longboard
- Have 6 months expenses in savings
- Remodel our kitched with limestone counters with fossils in them, old spanish tile floors, cheery cabinets, high end pro-gass range & stainless steel appliances
- Heli-boarding through deep powder
- Romantic diners with Julie at 5 Star Restaurants
- Surf a tidal bore
- Sunshine streaming into the windows of a new house I build or designed myself
- Scuba dive with hammer head sharks
- Give ‘Edward Bloom Days’ to people around me
- Die in peace with a smile
- Visit my parents often
- Spend time with Orianne
- Climb a 5.11
- Climb Mt. Kilamangaro
- A cute puppy
- California King Bed
- A home in a spanish speaking country
- Live in Nanny
- Play flamenco guitare
- Safari in Africa
- Eat wierd animals at the carnivore club
- Fall asleep every night knowing Julie is proud of me
- Be a leader of men
- Help provide a moderate presidential candidate – financially conservative and socially liberal by today’s standard
- Heal my back pain
- Grow an herb garden
- Eat grain fed beef
- Learn salsa dancing and go out with Julie
- Pay cash for daily living
- Light weight laptop
- Go deep see fishing and catch a marlin
- Surf whenever and where ever I want
- Ride horses through mongolia
- Tour New Zealand on bicycle
- Teach my kids to dream, set goals and push through failures
- Donate time and money to set up a teens entreprenurial project
- Donate time and money to set up a parent & child finance management class
- Support Julie’d charge for justice
- Have a strong friendship with my kids
- Create and teach a semester course on leadership to graduate students – after all they teach our kids
- Own a huge personal library
- Make Julie feel loved & love to my Julie often
- Surf Sunset beach
- Speak in front of a 100,000 people
- Get massages whenever I want
- Have friends all over the world
- Our kids feel like winners and know their parents are too
- Julie loves, respects and edifies me to others
- A car with air conditioned seats (I hate sweaty back)
- See my Abs on last time
- Make my children laugh & be the shoulder they can cry on
- Make people smile every day
- Inspire others to push beyond their own fears
- Take cooking courses with 5 star chefs in six countries: Italy, Morocco, Thailand, Japan, France, Lousiana
- Never run out of clean sox or underwear
- Buy Julie sexy Lingerie
- Take Julie somewhere with a beach, private cabana, reef, where its warm and she can wear those sexy clothes
- Sail around the pacific & ride amazing unridden rights
- Go to a couples retreat every years
- Have big weekend BBQs with friend on patio
- Good friend to share workouts with
- Never worry about the cost of medical
- Develop a strong relationship with mom and dad
- See antartica
- Be 20 feet away (safely) from an Orca in the wild
- See mardi-gras in new orleans
- Hike the trails in Machu Pichu
- Own a vehicle with a navigation system
- be positive and uplift people
- Help friends (& even strangers) in need
- See arches, zion and grand canyon
- Expand my circle of close friends
- Sit around and spend time with multimillionaires
- Go through pre-race / defensive driving school
- Surprise Julie with gifts
- Stay at the closest hotel to each business event
- Have lunch with Mark Victor Hansen
- Have dinner with John Gray
- Take a long walk with Joe Caruso
- Wake up to Julie’s genuinely happy laughter in the morning
- Overcome my fear of loosing my relationship
- Make my own furniture with dad
- Provide seed money for inovative business ideas
- Have time to cultivate intimacy
- Fly my kite with Julie & kids on a field of flowers basking in the sun
- Fly to good waves when its flat at home
- Live a life of purpose surounded by love
- Have on demand hot water and get pruned every day
- Take singing lessons
- Court my wife until the day I die
- Surf santa cruz island
- Go abalone diving and eat one
- Get 2 meal tickets at the culinary olympics
- Own a billboard on a major freeway where I can write whatever I want. Make people pause and think.
- Receive an x-mas card from the whitehouse