Entrepreneurial Lessons Learned The Hard Way

Below is my list of entrepreneurial lessons learned the hard way. Some cost me money and others cost me time. All of them cost me something. Here they are in no particular order:

  1. Listen and learn from people who have gone before because they might be right.
  2. A single entrepreneur “going it alone” can be a huge weakness. But not always.
  3. “Never give in” is not the same as “never give in, except to convictions of honor and good sense” – and knowing the difference can mean contentment – or pain and regret.
  4. Sticking to something is dumb if you are sacrificing housing or family for only money and ego.
  5. A cool office with nice furniture does not make a successful business.
  6. Having a partner in business is like being in a marriage. You can make mistakes together (and you will) but just make sure you work with a good person that values the relationship, isn’t into blame, and is into commitment.
  7. Slow down, focus in, think smarter, execute well. You will move farther, faster.
  8. Push the fear aside. Acknowledge it, but understand it for what it is.
  9. A deal is not closed when someone says they “might” buy from you.
  10. Networking is not about collecting business cards or how many contacts you have in your CRM. It’s about people. Put the focus on listening and learning and helping and your ability to network will improve. And you might actually enjoy it more.
  11. Doing the right research early is a key to early success.
  12. “No” is not a direct reflection on your own worth. Often, it means that for whatever reason, you didn’t present enough of a compelling reason for there to be a “yes”. There are times in life when you just need to settle for “no” and move on.
  13. Action and momentum generates a ready supply of opportunities.
  14. Having smarter people around you is smart and being afraid of smart people is dumb.
  15. Having good mentors is one of the most important things you can do early in your entrepreneurial career.
  16. Working with good people is always better than working with bad people. If you think the deal you are about to close is with bad people, walk away. Life will go on and you will be better for it.
  17. Good cash flow is fuel, and means less fear, better decisions, and ultimately, more happiness.
  18. Contain expenses always. There are exceptions but they are few.
  19. Don’t try so hard to be someone else that you forget who you are. The person in the nicer car on the road next to you is not necessarily happier than you – and in fact, they might have less money or liquidity than you.
  20. Having minority ownership in the business doesn’t mean you have job security in that business. In fact, it might not mean that much at all.
  21. If you are stretching yourself at work and in your craft, you will make lots of mistakes in life. And it’s important to build room for them into your plans. This might be the biggest lesson of all.

CHRISTOPHER MENGEL brings over 20 years of insights to business owners and talent leaders inside emerging technology and professional services firms to implement new initiatives, develop new strategies for growth, carry out organizational and cultural change, manage complex projects, and fill business-critical roles. Have a challenge you want to solve? Connect with him on LinkedIn and Twitter and subscribe to his posts or contact him.


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