23 Lessons from 23 years in business

On August 15, 1996, I packed up my cardboard box of belongings from my desk on the 30th floor of Barclay’s Global Investors in downtown San Francisco, and headed out to the elevator.

I was 29 years old, exhausted, and breathing heavily from the pneumonia I had developed from 10 years straight of striving, working full-time during the day and volunteering 30 hours a week on evenings and weekends running a non-profit capoeira group.

If you had told me on that day that I would never receive a corporate paycheck again, I would not have believed you. I thought I was taking a break from work to find another job that made me excited to work again.

Instead, I began the magical mystery tour that has been my 23 years in business.

I offer you some lessons from across the years.

And in the 23 days to follow, on LinkedIn and Facebook, I will share a short video with a story about each lesson.

  1. I don’t know, but I will find out.
    When I first started my business, I was a lot younger and had fewer years experience than some of my more seasoned and educated peers. Instead of stressing about it and trying to pretend I knew everything, I adopted the phrase “I don’t know, but I will find out.” It led me to learn so much, and connect with a huge network of subject matter experts.
  2. Trust your instinct, even when you are the least experienced in the room.
    Your value as an entrepreneur is not determined by the number of years you have spent being an entrepreneur. I have many younger colleagues (who I fondly refer to as “whippersnappers”) who run circles around me in certain areas of business. I love their confidence and talent. Trust yourself!
  3. Person first, then client.
    In all the years I have worked with clients, I have always spent time getting to know and value them as a person. What are their long-term goals? What do they value? What are they scared of? What do they love to do outside of work? What is their family life like? Do they have a partner, kids or pets? Knowing this information means that no matter how short or long the work engagement is, I can still cheer for them, encourage them and help them get what they want in life.This leads to decades-long relationships that often turn into new projects as people move from company to company.
  4. Arrive early and be prepared with a backup plan.
    When I was 5 years old, I remember my Dad was packing his bag to do a slideshow at a local community center. He put in the slide projector, extra lightbulbs and extension chords. “Always arrive really early and be prepared with extra equipment,” my Dad told me. I never forgot that. In hundreds of trips around the country to teach and speak, and in thousands of coaching conversations and online classes, I always try to arrive early and have a backup plan. It has served me well.
  5. Be a financial squirrel.
    I remember consulting in Silicon Valley in the late 90’s. It was intoxicating. Companies were giving recent college graduate engineers BMWs as signing bonuses. There was unlimited budget for hosting events and building programs. I didn’t have to do anything for marketing besides deliver great service, and I would get big, extended contracts. Then the crash happened. It was as if a bomb had gone off. Everything stopped. Having lived through a few financial cycles, I have learned how important it is to squirrel away money when the going is good for the times when the going is bad. Follow something like Profit First and you will be in good shape.
  6. We always know what is going on. Even if we don’t want to admit it.
    Every last bad experience I have had in business (tough clients, projects that went off the rails, difficult meeting facilitations) sent me big, bold signals in advance. Sometimes I tried to pretend the signals weren’t there. Sometimes I really needed money and said yes when I wanted to say no. I have learned to listen to my intuition and act on it.
  7. Test before committing.
    I once spent six months in deep development of a big program that ended up selling not one seat. I was so convinced that it was a good idea that I did not bother to try selling a much smaller program to see if it would work. So before you commit time, energy and money to a big project, make sure people are actually willing to pay for it.
  8. Be less optimistic about your pipeline.
    When you have a full calendar and bank account, it feels so good. You should congratulate yourself for making that happen. That does not, however, give you a pass from establishing a robust pipeline of clients and partnerships. Put marketing operations in place so that you never stop marketing, even in the good times.
  9. Trust and respect your colleagues.
    Have you ever been burned by a colleague or referral partner? It can be painful and awkward. Do not let this stop you from finding talented, trustworthy and responsible colleagues to work with. There is nothing better than knowing you are surrounded by people who respect you and your work, and will support your clients by delivering excellent service.
  10. Refer the hell out of your network.
    When you meet great partners, or find great products, that provide a solid solution for your clients, go ahead and refer them all the time. It is the right thing to do, and will generate lots of good will and referrals.
  11. Really listen.
    When my daughter is serious about making sure I am paying attention, she will take my phone out of my hand, turn off the music or the T.V. and say “Look at me Mom. I want to tell you something.” I am thankful she has enough self-awareness to demand my attention. She deserves to be deeply listened to, and heard. Your clients have the same desire. Even if you think you know what their needs are, even if you don’t want to spend too much time processing ideas or emotion, take the time to be fully, deeply present. I have the gift (some would say curse!) of holding space for a lot of emotion, and sometimes tears. Witnessing someone’s deep truth is a sacred experience.The truth is liberating, and is the root of doing great work.
  12. Don’t skip the first step.
    When someone comes to you and says “I would like to write you a big check for this project right now,” it is very tempting so say “Great! Let’s start!” Before doing so, however, you should make sure to back up and do some analysis and assessment like “how did you come to the conclusion that this solution is the right solution to the right problem?” Before jumping in with both feet, make sure you do your due diligence on all projects.
  13. Impact is more than income.
    A common metric used to calibrate business success (especially in the online world) is your annual sales. Is it great to make a lot of money? Sure! Especially where that is a core value for you and part of your deliberate business strategy. But what is also great is what your clients have accomplished with your help. What great things have you helped build? What problems have you solved? How much stress have you saved the family members of your clients by helping them stabilize their income? All this is a valuable way to use your gifts, and every bit as important as how much money is in your bank account.
  14. When in doubt, do it.
    Some of your ideas are great. Some are spectacularly bad. But the only way you will ever be able to tell which is which is by testing them with real people with real money in the real world. Don’t write off your ideas too soon.
  15. It is actually *more* painful than you think.
    I love the freedom of working for myself. It is amazing to be able to work with clients all over the world. AND … it is really, really hard work. Much harder than I ever would have anticipated. And the more time I have been in business, the more I see that is the constant for entrepreneurs no matter the stage or level of income. So … bad news, it never gets easier. And good news … it never gets easier, so you stay sharp and fresh and innovative.
  16. Trust your craft.
    I spent my formative years at my Dad’s knee, watching him take, develop and analyze photographs. Until the last months of his life, he was still passionate about his craft, and loved discussing it. I feel the same about my craft of coaching, and writing. I love them. I respect them. And I want to do right by them.
  17. Take deep breaths. Frequently.
    The more stressful things become, and the faster the pace, the more you need to slow down and take deep breaths. Really.
  18. Gratitude every day.
    The day I stop being grateful for the people I get to work with and the work I get to do is the day I will close up shop. I never, ever take for granted the trust my clients put in me to help them solve their problems, and build something great together. This gratitude fuels my energy, optimism and creativity.
  19. It is easier to sell a solution than solve a problem.
    We all want instant solutions. Doesn’t it sound exciting to solve all your cash flow woes with a business blueprint or coaching program? The problem is, true resolution is more complicated. Don’t be fooled by flashy solutions that promise to fix all your problems. And beware of creating a sales pitch that promises instant results.
  20. You can’t outsell, or outrun, your ethics.
    When you cut corners, or make a decision that goes against your values or ethics, it will catch up with you. When you partner with people who are sketchy, you will impact your brand, and your heart. Stand on your ethics, even if it costs you friends, money or opportunities. You will thank yourself in the end.
  21. Ideal clients accelerate your gifts.
    There is a magical alchemy that happens when you work with ideal clients. You feel the presence of your gifts and superpowers. They appreciate your guidance and expertise so much, and tell you so. Together, you build things that neither of you thought possible. The opposite can be said for non-ideal clients.
  22. We all need each other.
    It is a myth that you can solve all your problems yourself. None of us can. Instead of flailing around trying to figure it all out yourself, ask for help. Surround yourself with people who have your back, and will call you on your bullshit. Put your energy into your community and make life easier and better for your neighbors.
  23. Hope is an action, not an outcome.
    Boy are a lot of things screwed up in our world right now. But you know what? We have serious gifts and tools. When we put them to use, we can and will turn things around. Build hope. Inspire hope. Inhale problems and exhale hope. We are all we got.

I plan on being here until I can’t lift my hands to the keyboard, so I look forward to sharing more lessons with you as I jump into the next 23 years.

Reader Interactions


  1. Jose says

    Pamela , I am not sure if you are the author of “Scape from Cubicle Nation”.
    I am from Republic of Panama and I am looking for inspiration to make my life free and shield myself from the system.
    I am already very grateful that people like you exist.
    Best Regards.

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