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November 6, 2018 41 min

Many of the people who listen to Converge are creatives – freelance photographers, artists, interior designers, and others. They know that moving from the time-for-money trade that freelancing requires to the establishment of a business as an entrepreneur is not easy. If you’re reading this, you are likely one of those people.

David Jay is a guy whose journey from freelancer to business owner was very natural in terms of how he was gifted, but that doesn t mean it was easy. He s experienced many obstacles along the way, the biggest one being himself. Join Dane and David for this revealing conversation. It highlights the valleys of self-discovery we all have to walk in order to become the best version of ourselves, which in turn equips us to bring our best to the world we are meant to serve. You ll enjoy this episode.

When you only have one option, you tend to find a way

One of the situations that David found himself in was centered around the tension he felt while he was trying to finish up his college degree. He knew he wanted to do things outside the realm of the education he was getting, and he felt he should do them right away. He decided to drop out of college and pursue his dream of being a freelance photographer. To him, it was an intentional choice of putting his back against the wall so that he had to make his choice work.

Once he did that, it didn t matter how many people criticized his decision or felt he was heading in a bad direction, the desire to prove his worth in spite of having no degree fueled him. It wasn t the best motivation, but it worked for a while. Today, even David says that at some point you want to get beyond that kind of ego-driven motivation and find something that matters more. You ll hear David s personal journey including how he came to discover his own “something more” if you take the time to listen.

As a freelance photographer David tried to focus on serving people – and he always had plenty of work

Once David made it past the stage of trying to prove himself to his critics, he remembered something his father said to him.

If you focus on serving people, you ll always have enough work.

He made the shift, centered his photography business around doing what was best for his clients, and he found a new satisfaction in what he was doing as a freelancer.

But his entrepreneurial itch wasn t being scratched. He had to do something more, something bigger and aimed at serving more people. So he began creating products that could serve those who were in the same shoes he wore: freelance photographers. You ll hear about some of the amazing products he and partners have created, how those businesses are doing today, and how he discovered that the entrepreneurial road is one of the best paths to discovering who you are, warts and all.

Don t be an idiot and quit your job: Let things play out as they should

We ve all heard the amazing stories of people who gave up everything to pursue their dreams. But we usually only hear about the successful versions of that familiar tale. There are many who don t fare so well. David never recommends that a person with a family that is depending on their 9 to 5 paycheck should drop their job to pursue a dream. Instead, he suggests you work at your dream on the side, in increments, waiting for things to play out as they should. When you do, you ll be amazed at how much you can accomplish through small steps over time.

This should be an encouragement to all of you who find yourselves stuck in a job that isn t fulfilling. It shows that you can create your own fulfillment and grow it into something larger than you can even conceive if you stick to it and put in the work required.

Build your product and business around the gifts you have – happiness will follow

David s journey illustrates how success without fulfillment is a very empty thing. Through his struggles and the things they revealed about his own character, he was able to discover an ongoing, repeatable cycle of growth: learn about himself, make an adjustment, and pivot toward a better direction.

One of the most powerful things he learned is that he didn t have to build his business like everyone else. He didn t have to follow an entrepreneurial model that wasn t aligned with his personality or gifts. Instead, he learned to build his business and his services around the gifts and strengths he had. And guess what – he was more happy doing it.

Don t miss this episode. David s honesty and humility are a refreshing antidote to the formulaic approach to the entrepreneurial path you hear these days. He’ll give you some practical, wise advice to follow.

Outline of this great episode
  • [0:22] The creative life of a freelancer and how it can morph into entrepreneurism
  • [1:45] Dane s testimony of how David is the kind of guy you want to model your life after
  • [3:09] David s career – college drop-out, photographer, freelancer, entrepreneur
  • [7:36] The better motivations you can use to drive yourself forward
  • [9:29] Service to others provides you plenty of opportunities to make a living
  • [11:32] It took a downward spiral to put David s life into perspective for him
  • [13:27] The slow realization that scalable products were a better path
  • [17:25] Forcing things into existence before they are ready is a sure way to get burned
  • [20:22] A rule of thumb for telling if an idea is ripe: listen
  • [26:01] Learning what feedback is helpful and how to kill your baby (product idea)
  • [28:57] How to develop the self awareness to understand what you should do
  • [34:52] Healthier than ever in the pursuit of things – and the ripple effects that ensue
  • [36:21] The best place to start to get your life in order: common language
  • [38:48] The future of entrepreneurship – from David s perspective
  • Resources & Links mentioned in this episode
  • SPONSOR : White House Custom Color :
  • BOOK : Love Is The Killer App :
  • Pictage :
  • SmugMug :
  • Facetime :
  • – a photo gallery run by one of David s former partners
  • Giant Worldwide : – leadership & coaching company
  • Myers Briggs :
  • David Jay s Resources
  • Pass : – David s photography gallery tool
  • Follow David on Twitter:
  • – one of the services David created
  • – One of David s services
  • Connect with the Converge team:





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