In this episode: Jon Peyton pulls together the season so far (mentality, the dream, the journey, drive, network and relationships) to ask what success actually means. He shares how his own definition has moved from decisiveness to financial security to relationships. He also explains why success has to be defined in concrete terms before you can measure progress toward it.
Key insights
- Success means different things to different people, and your own definition will change as you move through stages of life.
- For an entrepreneur or executive to succeed in other areas of life, the business itself usually has to succeed first.
- Jon found that the more he helped others reach their goals, the more his own success followed.
- A vague goal can’t be pursued. Define success as a specific benchmark so you know what you’re working toward.
- The further away your goal, the harder it is to stay focused. Track progress so you can see the distance you’ve covered.
Episode timeline
- 0:00 Bringing it all together
- 0:52 Success is defined in many ways
- 2:51 Jon’s definition: time with people and the impact he makes
- 3:12 Early career: success as speed and decisiveness
- 4:52 Shifting the metric to financial security
- 6:25 Success through other people’s goals
- 6:50 Relationships: the hardest kind of success
- 9:50 How success shifts with each stage of life
- 12:20 What does success look like to you?
- 13:05 From scatter-brained to a clear benchmark
- 14:55 Distant goals require patience
- 16:00 Were you really committed?
- 19:00 Owning your weaknesses and asking for help
- 20:55 Commit to the process
The episode in brief
Pulling it all together. The season so far has covered mentality, the dream, the trend, the journey, drive, network and relationships. This episode asks what all of it is for. Success might mean a good family life, a strong relationship with your team or financial security. Usually, though, for a founder or executive to succeed in those areas, the business itself has to succeed and keep growing.
Jon’s definition has changed over time. Today, success for Jon is about time with the people he wants in his life and the impact he has on them. Early in his career it meant being the best at what he did. The more he tried, tested, validated and iterated, the faster he could break problems apart and make decisions, and the less stress he carried.
Then the metric shifted to money. Jon wanted financial security and the means to provide for his family, without draining the business or the people helping him build it. The breakthrough was asking his team what their goals were. The more he helped others succeed, the more success came back to him.
Then it shifted to relationships. Jon admits this is the area he struggles with most. Time spent helping others succeed can crowd out time with friends and family, and long nights at the office can feel lonely. His goal now is emotional success: investing in the relationships that make the rest of life feel complete. He believes being more well-rounded will make him a better business owner too.
Define it, then measure it. What does success look like for you, in your household, your relationships and your business, at your stage of life? Once you’ve defined it, you can set a benchmark, whether that’s an income level, a personal milestone or something else. Too often we approach goals in a scatter-brained way: we know roughly where we want to go and have no idea how to get there. With a clear target, you can work backward through planning, trial and error.
Distant goals take patience. The further out the goal, the harder it is to stay focused, much like weight loss when the scale barely moves. Look back at how far you’ve come. If you did everything right and progress is slow, it’s just taking time. If you skipped the work, be honest with yourself: maybe the goal wasn’t truly a priority.
It’s in your hands. Success depends on mentality, the right traits, a clear plan and the discipline to stick with it. Acknowledging your weaknesses, and who can help you overcome them, is half the battle. And when you fail, learn the lesson: fail fast, fail often and fail upward.
Key action items
- Write your current definition of success. Cover your work, your relationships and yourself, and note what stage of life you’re in.
- Turn it into a benchmark. Attach a specific, measurable target and a time frame to at least one part of that definition.
- Ask the people around you about their goals. Find one way your work can help a team member or family member move toward theirs.
- Review your progress monthly. Look back at where you started, and be honest about whether slow progress means “it takes time” or “I wasn’t committed.”
Listen next: Episode 9: Bridging the “Oceans” of Entrepreneurship
This episode is educational and isn’t legal, tax or financial advice. Speak with your own attorney and advisers about your situation.