Fifteen years ago yesterday, on August 16, 1996, I rolled over slowly in bed.
My head was throbbing. I could hardly breathe. I felt weak.
It was my first day as a self-employed person.
I was in the middle of a wicked bout of pneumonia, and at that point, all I knew was that I no longer could keep up the grueling pace of full-time corporate manager by day and non-profit Executive Director and martial arts instructor by night and weekend.
I had no idea that the choice to get back to good health would lead to some of the most exhilarating years of my life.
In fifteen years, my path has led me from consultant to large corporations to coach to hundreds of individuals wanting career change, to teacher to thousands who want to start a business, to author and speaker about leading in the new world of work.
I have learned a few things in these fifteen years, and most have nothing to do with the nuts and bolts of business plans.
- Your biggest weakness can become your greatest asset.
Let’s face it, I am a hippy. I like to do good in the world. I like to build meaningful relationships. I reduce, reuse and recycle. And I believe in reciprocity — giving at least as much as I get. At various stages in my career, mentors have chided me for not being more “hard,” caring less about impact and more about the bottom line. I have carefully weighed their advice and made significant shifts in my sales process and business strategy to make sure I am getting good value back for my investment in energy. I have also learned that focusing on more than the “hard” side of business has been a tremendous strategic advantage as I have built a large community of friendly, supportive blog readers and clients who care as much about making meaning in the world as they do about making money. My friend Dave Rendall calls this your Freak Factor in his excellent book of the same name. - Learn from your triggers.
When you get clear on the kind of business you want to run and how you want to run it, chances are you will also get clear on who represents the polar opposite of your style. You may be a master craftsperson and get triggered by a flamboyant marketing person. You may pride yourself on being tuned in and sensitive to the needs of your customers and get triggered by people who use saucy and abrasive language. I have learned from many years experience that very often, people who trigger me have very important things to teach me. And if I shut out ALL of their advice just because I dislike their style, I can miss out on tremendous opportunities to grow. The mentors I mentioned in the above point are examples — if I had totally rejected their advice to be more strong and clear on the “hard” side of my business, I would not have achieved the success I have. - You must define your own success.
I think comparison must be part of how we are hard-wired as humans. New babies probably check each other out in the nursery and think “Man, why did he get such a soft blanket when I have this scratchy one?” Distinguishing ourselves from each other helps to define our own identities. As we grow, comparison can eat us alive. Each one of us makes different choices about how we spend our time, how often we work, what we eat, what we create and how we make time for family. Comparing yourself to a peer’s output instead of your own leads to Success Dysmorphia. My definition of success is “enjoying living my life while I am living it.” What is yours?
- Nothing substitutes for substance.
It can be frustrating to watch new kids on the block zoom to fame and fortune after you have been slogging in the trenches for years. Sometimes they are lucky. Sometimes they are just frighteningly talented. Instead of wasting energy with envy, learn from the good things they do, and don’t worry about the superficial parts. I go grumpy old school some days because I know from so many years training martial arts that it is impossible to build mastery in a body of work without also building muscle. If you are marketing a crappy product, even with the best tools and persuasion techniques, sooner or later your market will find out it is crappy.
- Peers are oxygen.
I get a lot of questions from the press about the “ideal characteristics”of new entrepreneurs. “Do you need an MBA?” they ask. “Can introverts be entrepreneurs?” “Which Meyers Briggs Profile is most likely to succeed in business?” I say the same thing in almost every interview: Regardless of your strengths or weaknesses, if you do not have a stellar circle of peer mentors around you, you will not succeed in business. There are precious few people who have a totally balanced skill set and can move between brilliant strategy to brilliant execution to dazzling persuasion and sales. You will get stuck, and feel scared, and need advice regardless of who you are. Your peers become as significant to you on your business journey as your best friend from college or your parents or spouse. Choose wisely. Without partners like Charlie Gilkey, Michele Woodward, Desiree Adaway Andrea Lee and Jonathan Fields and young mentors like Willie Jackson, Ramit Sethi and Shama Kabani, and High Council members like Seth Godin, Martha Beck, Tim Berry, Nancy Duarte and Guy Kawasaki to look up to, I would be lost.
- The bigger you get, the more you have to say no.
My business partner Charlie Gilkey said it well this weekend at Lift Off: the first two stages of business are about saying YES and the last two stages are about saying NO. Most new entrepreneurs come brimming with new ideas and approaches and rightly spend most of their time testing and trying new ideas. Once you get some traction and your business starts to boom, you will burst at the seams if you don’t make some decisions about what is really important to you and will yield the best results. Learn how to say no.
- Fame and money come and go. Impact endures.
When I consulted in Silicon Valley, I knew a lot of very wealthy people. They drove really fast and expensive cars and ate lots of sushi and worked in cool places with ping pong tables and fancy chairs. A few not only were great at their work but really loved it as well. The vast majority of them were sprinting through life afraid that a tidal wave would hit them if they stopped producing. Many created PowerPoint slides about incomprehensible things and pitched products that few people truly understood. When things came crashing down in 2000, many were devastated to step off the gravy train. But others not only survived, they thrived and grew the next wave of great products and services. Make sure that you are not only proud of your body of work, but humbled by the impact it has on people you care about deeply. And if you are an educator/coach/teacher and anyone ever questions the value of what you provide, send them a link to this video.
- You grow as your business grows.
I know I am a better businessperson after 15 years in business than I was when I started. I also know that I am a better person than I was 15 years ago. Business changes you and forces you to grow in strange and wondrous ways. If you don’t grow in a positive direction, sooner or later your business will begin to get sick. Which is why I think going into business is the best personal development on the planet. - When you don’t evolve, you go backwards.
Your people WANT you to grow. And when you don’t, they go elsewhere. Nothing in the natural world stands still — it is born, it grows, it withers, it dies. And it is used as fertilizer for the next thing that grows. You are not serving anyone by staying stuck. Don’t be afraid of what you don’t know — as you grow, you will find that the right people will find their way to help you. Everything is scary and uncomfortable at first.
- Optimism is a business asset.
The economy grows. It shrinks. Industries boom. They bust. Fortunes grow. They shrink. People flourish. They crash and burn. What keeps this strange cycle going after a big shock of disappointment is that someone says: “I believe it can get better. I believe it will get better. And here is how.” Very often, those people are entrepreneurs. Crazy, stubborn, head in the clouds, pie in the sky hope-filled people who believe that if something was made from nothing once that it can be made again. If one person hit rock bottom and somehow found the strength and courage to get up and create a new life, then it can be done again.
That spirit is what I am proud to be part of.
Here is to another 15 years!

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