G89. Dan Sullivan

The Pursuit of Happiness & Measuring Progress Backward with Dan Sullivan

Dan Sullivan is the Co-founder of Strategic Coach, an organization built to grow entrepreneurs into their best selves and unlock the full potential in both their business and personal lives. An innovator and gifted conceptual thinker, Dan has over 40 years of experience as a strategist, coach, consultant, speaker, and writer, having authored over 30 publications, with his latest, The Gap and the Gain, out now!

From an early age, Dan saw the raw power and positivity that was up for grabs if you simply apply yourself in a strategic manner. You can hear this in the stories from his time spent in the Army as you can from his time paying his way through college. Before landing into an oeuvre, helping entrepreneurs achieve their best, Dan even worked for the FBI – and, once again, saw the potential that everyone around him was missing by simply taking a step back and analyzing how things worked. 

Dan’s philosophy is built on the idea that we can’t measure progress by looking forward. It’s only possible when we look back and see how far we’ve come. And one of the best ways to do that is to focus in on happiness. When it comes to success, what better metric is there than how happy something makes us?

There’s no point in being a contrarian for the sake of it, but as Dan says, sometimes, one of the best moves is to take a look around you, see what everyone else is doing, and then do the opposite. You’re bound to find something they missed and you’ll no longer be following the protocol – you’ll be finding your own way and the positives that come with that are numerous.

He has so much incredible insight to offer, both for those of us with entrepreneurial leanings and for those of us who’ve never dreamed of running a business, too. I’ve found his teachings profoundly useful in my own life, so it’s a pleasure to be able to share them with you on the Gravity Podcast. 

What Brett asks:

  • [01:23] Can you start at the beginning and tell us about your upbringing?
  • [06:30] Did you have a desire to figure stuff out and crack codes as a kid?
  • [13:28] How important is having a childhood to allow someone to discover who they are?
  • [19:46] Let’s talk about your path into being an entrepreneur.
  • [39:30] Tell us about your entrepreneurial venture before you launched Coach
  • [48:20] Has learning from other people’s behavior shaped Coach?
  • [53:30] Expand on the concept of happiness

Lessons for intentional living:

  • One of Dan’s biggest philosophies is the idea that we can only measure progress by looking backward. There’s no use in looking forward and paralyzing ourselves with life’s “could’ve”s. Instead, we should look back and assess what has and hasn’t worked – what we did wrong and what we did right.
  • Becoming an entrepreneur can be daunting for so many reasons, but if you have that drive, you owe yourself to go for it. As Dan says, it’s one of the best shots you’ll have at living the exact life you want to live.