20 Lessons from 20 Years of Running My Own Business

Thoughts on Excellence Free E-Newsletter Series
Volume 16, Issue No. 9b
January 15, 2018

By Dan Coughlin


Wow, 20 years goes by fast.

On January 15, 1998 I walked out of my classroom at St. Louis University High School as a math teacher for the last time. Tom Becvar took a picture of me standing next to a statue of St. Ignatius of Loyola, the founder of the Jesuits, and I drove home.

Tom was the major influence in my life for the 20 years preceding that day. He was my high school math teacher for three classes and my advisor, he hired me to teach at SLUH, he was the Math Department Chairman, and he was in my wedding. Since I’ve spent these past 20 years as a corporate teacher and coach, I think it’s fair to say that Tom had a greater influence on my business career than any actual business person.

Here are twenty lessons I’ve learned in the past 20 years of running my own business. I hope some of them are of value for you.

Lesson #1: Find really good mentors

You don’t know what you don’t know. Find someone who has been down a similar path before you.

On January 18, 1998 I had the enormous good fortune of listening to Alan Weiss. I heard him speak again in August 1999, and then I hired him to be my mentor. Little did I know that he would become the #1 mentor in the world for independent consultants. For the next eight years I followed his fantastic advice on every part of my business, and that made an enormously positive difference. I knew basically nothing about how to run my own business on day one, and Alan filled up my blank slate.

In 2008 I met another famous guru, Jason Jennings. For some wildly inexplicable reason Jason took me under his wing and encouraged me and kept feeding me positive reinforcement over and over and over again. I still don’t know why he was so kind to me, but he encouraged me through The Great Recession and beyond.

Recently I’ve been influenced by Seth Godin who is both a great teacher in explaining ideas and great at providing mind-expanding and paradigm-changing ideas.

Find a mentor and be willing to consider his or her ideas. Don’t follow them blindly, but always consider them.

Lesson #2: Write down your ideas as they come to you

Keep a blank journal close by you at all times. Since my senior year in college I have filled up 29 blank journals with ideas and memories. I’m halfway through journal #30 right now. About 12 years ago Roy Spence, the head of GSD&M Idea City, told me that ideas are the modern currency. He’s right. A powerful idea is the starting point of habits and products and services and shifts in the way people buy and what they buy.

Always write down your ideas and read them over frequently.

Lesson #3: Try at least one new idea each time

Patricia Ball is a National Speakers Association Hall of Fame speaker. When I was just starting out she said to me, “Always try something new in every presentation. Don’t ever just do an old speech the same exact way for a new audience.” Thank you Patricia. Thank you Patricia.

Whatever you do in your business, keep tweaking and adding little by little. If you do that you will quickly become better and better and better.

Lesson #4:  Read to feed your brain a range of perspectives

Read books. Don’t hesitate, don’t argue with me, and don’t doubt my advice. Just read books. If you read one book a month, that’s 12 books a year. That’s 120 books in 10 years. That’s 240 books in 20 years. If you just do that, you will be in the upper few percent of the people in the world in terms of feeding your mind with a wide range of perspectives.

Lesson #5: Exercise regularly

You have to be in shape to handle all that is involved in running a business. There are so many curveballs and changes and surprises that you have to be in shape to be able to keep on going. Walk regularly, play tennis, do anything, but do something to stay in shape. I need to reread that one every day.

Lesson #6: The worst 4-letter word and 8-letter word in business

I think the most disgusting 4-letter word in business is d-e-b-t.

The worst 8-letter word is i-n-t-e-r-e-s-t.

Nothing creates more pressure in business than debt. And nothing sucks the energy out of a business more than having to work just to pay off the interest on your debt.

I know. I’ve been there three times over the past 20 years. I made some remarkably dumb moves, and then I would lay in bed at night and wonder how I was going to get out of debt. Then an idea popped into my head. Don’t spend a lot of money on any of my crazy ideas, and don’t spend any money on most of my crazy ideas. Be patient. The market will eventually open up to me for a brief moment. Be ready for those moments. Being completely out of debt allows me to be very selective in who I work with, and that has completely changed my business. Now I never take on work with people I don’t respect and don’t enjoy being with.

Lesson #7: Reach beyond your current grasp

Don’t lock yourself into a narrow little world. Always reach beyond where you are today.

In 1996 and 1997 I gave over 60 free speeches at high schools, senior living facilities, Kiwanis clubs, Optimist clubs, and on and on. I wasn’t very good, but each time I got a little better.

Tony Ruesing, one of my mentors in St. Louis suggested I should speak for a public seminar company. In 1998 and 1999 I did over 40 seminars for the American Management Association. I sharpened my skills, and I was ready to reach again beyond my grasp.

Then I started working with some small companies. Then I got a few breaks and started working with people at McDonald’s, Marriott, Coca-Cola, RE/MAX, Toyota, Cisco, and about 200 other companies. Each time I would reach just a little bit beyond where I was at any given moment.

Lesson #8: You never know who will open a door for you or how big the room will be

Don’t ever, ever, ever write someone off as being insignificant in your career. You honestly don’t know who you are talking with or who they know. The biggest break of my career came because I gave a free speech at my high school when I was still teaching. I asked Kevin Dunn, the head of the McDonald’s St. Louis Region whose son was in my math class, if he wanted to speak at the event. He couldn’t make it, but he introduced me to a guy named Lee Renz, who was a multi-department head for McDonald’s. Lee and I met in December 1996. That breakfast meeting led into an enormous amount of work for McDonald’s over the next 10 years.

Fifteen years later I gave a speech two hours north of Toronto in November 2011. It was snowing so hard in Chicago when I transferred planes I didn’t even know if I was going to make it. That speech led into a remarkable relationship with RE/MAX.

During a speech to a group of professional speakers in St. Louis in 2002 I offered to meet with any of them for free to discuss their business. I met with about a dozen of them one-on-one for a few hours each. 12 years later one of those people remembered me, and recommended me for a variety of projects at the Washington University Olin Business School.

You never know who will open a door for you or how big the room will be. Treat every person you meet with total respect. You have no idea who you’re talking with or how big the room is that they might invite you into.

Lesson #9: Play your aces every time

Never, ever do less than your best. Always give the very best value that you can give in whatever you do. Never save your best for a later date. Here’s the reason: if you give your very best today, you will learn how to be better tomorrow. And that’s the fastest way to really stand out in a crowd. If you only give 50% of what you are capable of giving in order to save your best effort for a really special moment, you will never get better. You will never exceed your current best because you will never put your current best on the table. You will always save it for the “right moment,” which never comes.

Lesson #10: The power of accumulated effort

In November of 1999 Alan Weiss heard me say that I wrote a 2-3 page feedback letter after every executive coaching session. He said, “Dan, you like to write. I want you to write four articles on the topics you talk about and coach on, and then send those articles to 50 people you know.”

Wow, that was good advice.

Since then I’ve written more than 400 articles on the topics I focus on: personal effectiveness, leadership, teamwork, strategy, execution, innovation, and branding.

Whatever you do that adds value to other people, keep doing it over and over and over. That accumulated effort will consistently generate breakthroughs in what you are capable of delivering to other people.

Lesson #11: Reflection and Discernment: the two most underrated words in all of business

Stop. Stop working. Stop doing. Stop running around. Stop being productive.

Step back. Breathe. Slow down. Reflect on what you’ve done. Discern what worked well and why, what didn’t work well and why, what you’ve learned, and what you will do the same and what you will do differently going forward. Pause and reflect and discern.

Then move forward again by applying what you’ve just discerned.

Lesson #12: 4 Key Guidelines: Open-mindedness, honesty, respectfulness, and caring

I’ve found that these are the four key guidelines for every meeting. I’ve learned to start every seminar and every meeting that I facilitate by explaining the importance of those four guidelines. They have made a huge difference in the quality of the conversations.

Lesson #13: The exponential value of collaboration

In working with people at McDonald’s I learned a great quote from Ray Kroc, “None of us is as good as all of us.” I’ve never been in any situation where one person had all the best ideas. The best ideas popped up from different people in the room. The key was willing to be respectful of everyone so that no idea was dismissed too early.

Lesson #14: The power of one-to-one conversations

Magic happens in the privacy of a one-to-one conversation. People open up in ways that I never would expect. This private environment allows people to share their fears and dreams and aspirations and self-doubt and self-confidence in ways they never would in a group conversation. This has been my primary activity over the past 20 years in my Executive Coaching work. It has been the honor of a lifetime to be in over 4,000 of these private conversations with people in a wide range of companies and titles and functions.

Lesson #15: Make time for other people’s toughest moments

People die. Marriages fall apart. Young people fall into dangerous habits.

You don’t know when these incredibly tough moments are going to happen to people you care about. It’s okay to put your business work to the side and be there for other people. Some of my most poignant memories over the past 20 years are when I went to the funeral of a friend’s father or mother or husband or wife or son or daughter. 4 times I’ve been asked to give a eulogy, and those brief remarks stand out in my memory because I was so honored to be asked. And I remember when people stopped their busy work lives to come by my side at my dad’s funeral and my father-in-law’s funeral and my sister’s funeral.

Make time to show up at other people’s toughest moments.

Lesson #16: Never stop writing handwritten letters

My mom is and my dad was a voracious writer of handwritten letters. Neither of them went to college, but their letters were as powerful as any book I’ve read.

This is a very simple habit to develop. Get a stack of 50 pieces of paper. Fold them twice so they fit into a #10 envelope. Buy the envelopes and put one sheet in each envelope. Keep that stack by your desk. Every few days reach out and grab an envelope with a sheet in it, and write someone a letter of appreciation or encouragement.

That’s it. You’re done.

Lesson #17: Know your roles in your business

In my business, I know my roles. I am a teacher, a coach, and an advisor. It’s actually the same roles I had 30 years ago when I worked in high schools and colleges. It’s the roles I learned from Tom Becvar and Ebbie Dunn, my high school soccer coach, and Dennis Grace, my college soccer coach. I no longer teach math or coach soccer. Today I teach and coach and advise on ideas for achieving desired outcomes in a sustainable way.

What’s your role in your work? Be able to explain it to another person.

Lesson #18: Don’t arrive, keep going

I have never arrived. I’ve never felt, “Yep, I’m done.” I’m still learning, still trying, and still honing my craft. I plan to never arrive, but rather to just keep going.

Don’t obsess over a retirement date or hitting a milestone. Just keep going, keep learning, keep trying, and keep honing your craft.

Jimmy Stewart said his ultimate goal as an actor was not to win an Oscar, but rather to keep honing his craft. That’s one of the many reasons I admire him so much.

Lesson #19: Actually do what you encourage others to do.

The world’s easiest job is to give advice to other people.

The world’s hardest job is to actually do what you encourage other people to do.

Whenever you face a problem, imagine that it’s someone else’s problem. Then ask yourself what advice you would give to that person on how to solve that problem. Then put your advice into motion for yourself.

Lesson #20: Reach for daily excellence.

I love the word excellence. To me, excellence means to do the best you are capable of doing today while simultaneously learning how to do it better tomorrow.

If you do that every day of your working life, you will be a shining star in your industry and you will have an enormously positive impact on lots and lots of other people.

Bonus: Take real vacations consistently

And this one I owe to my wife, Barb. When I met her in 1995 my idea of a vacation was to hang out with my buddy, Jeff Hutchison, for three days. After grade school I had never traveled anywhere to go on a vacation for a week with anyone or by myself.

Barb explained very clearly to me that we were going to go on real vacations. Thank you Barb, thank you Barb, thank you Barb.

I now fully realize the benefits of taking real vacations that reenergize me and balance me and prepare for the next work adventure.

Right now write down three real vacations you are going to go on in the next year or two.


Wow, that was fun to write. Sorry it got so long. 20 years went by in the blink of an eye. It has been remarkably fun and exciting and exhausting and stimulating and frightening to be an entrepreneur. I recommend it to anyone who wants to wake up every day and have absolutely no idea what the future holds for you. Life is a blank slate. Now go fill it up with your passion and purpose and talents and ideas and efforts.

Republishing Articles

My newsletters, Thoughts on Excellence, have been republished in approximately 40 trade magazines, on-line publications, and internal publications for businesses, universities, and not-for-profit organizations over the past 20+ years. If you would like to republish all or part of my monthly articles, please send me an e-mail at dan@thecoughlincompany.com with the name of the article you want in the subject heading. I will send you the article in a word document.

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