Jeffrey Harry

Creator of Rediscover Your Play

Jeff Harry combines positive psychology and play to help teams/organizations navigate difficult conversations and assist individuals in addressing their biggest challenges through embracing a play-oriented approach to work. Some of the topics he covers including how to deal with toxicity in the workplace, how to address office politics, how to play with your inner critic, how to help your staff rediscover their flow, and how to navigate these uncertain times through play. For his work, Jeff was selected by BambooHR & Engagedly as one of the Top 100 HR Influencers of 2020. His work has most recently been featured in the NY Times & Mashable. You can check out some of his interviews here:

Where did the idea for Rediscover Your Play come from?

Ran team building events for some of the top tech companies in the world (I.e., Facebook, Google, Adobe, Paypal, etc.) and found that even though they spoke about innovation, disruption, agile, they weren’t actually creating psychologically safe spaces for their staff to take risks and play

Created Rediscover Your Play to tackle those hard conversations and address those major trust issues at work using positive psychology and play.

What does your typical day look like and how do you make it productive?

A typical day looks like creating a TikTok video to start my day. I usually do 1 – 2 podcast interviews. I connect with companies that I’m running workshops with. I respond to Help A Reporter Out requests and also collaborate with some of my fellow play colleagues on projects, edit videos for paid collaborations, and when I have availability, connect with like-minded people on apps like Clubhouse. Every day is quite different, but always full of play.

How do you bring ideas to life?

Because I’m a play guy, I’m all about experimentation. I test workshops for 5 months before I roll them out to clients. With videos, I make short versions of them, and the ones that resonate most with, I expand into longer, more in-depth videos.

What’s one trend that excites you?

The emergence of TikTok and how the app allows people to play so much, especially when people are seeking connection in this isolated pandemic world.

What is one habit of yours that makes you more productive as an entrepreneur?

I start my day with play. By priming my day with play and asking the question, how can it get any better than this, with curiosity, it helps me have a phenomenal day that I savor.

I add to it by asking the curious question, “how can it get any better than this?” By doing this, I’m priming my mind to look for patterns on how the day can get any better than this, thus changing my entire day.

What advice would you give your younger self?

Double down on being your weird, nerdy, authentic self. Your belief that no one really knows what they are doing and that we are all making it up as we go along is true.

Tell us something that’s true that almost nobody agrees with you on.

You can play your win, becoming super successful. Most people think you must be serious about getting there, but I have found the opposite.

Also, the idea of embracing death really helps you to appreciate and really live your life.

One more, you have all the answers that you need. Any advice you have resonated with, you have already told yourself that in the past. That person is just a reminder that you have it all. This can be most a scary and empowering realization.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Get bored (I.e., block out social media and binge-watching Netflix) and listen to your inner child, and follow your curiosity from there. You have all the answers you’ll ever need, and you need to play enough to figure it out.

What is one strategy that has helped you grow your business?

Focusing on building habits over trying to achieve specific results. I have accomplished more with a strong outreach habit than me trying to hit a certain revenue mark. Expectations are the thief of joy, and when I get too fixated on a result, and I don’t achieve, it can be really unmotivating. When I am simply embracing my habit, though, I might achieve the result without realizing it because my intentions and not my goals drive me.

What is one failure you had as an entrepreneur, and how did you overcome it?

I lost six figures on a business I invested in. I ended up paying off the debt over many years, but I realized that I was stronger than I thought, and that failure made me so much bolder going forward. Now, I’m all about taking a risk a day as you never know what that one risk may take you.

What is one business idea that you’re willing to give away to our readers?

During this pandemic and isolation, we are missing touch with has a huge effect on our mental health. If I had the time, I would work on making a lifesize stuffed animal that gives really great hugs whenever you need them. Your friends could even send you a huge digitally and their voice would come out when you hugged the life-size stuffed animal. That’d be my invention to help the world right now.

What is the best $100 you recently spent? What and why?

I spent $100 on a ring light, which helped me during the past 9 months when I was able to do over 100 interviews and create over 150 videos. Totally worth it.

What is one piece of software or a web service that helps you be productive?

Clearbit. Clearbit helps me finds contacts at specific companies to reach out to certain departments. I have been able to create outreach lists from this. It is a google chrome extension that works with Gmail, and it is quite helpful.

What is the one book that you recommend our community should read and why?

I have two recommend two.

The Big Leap By Gay Hendricks

He explores how you can discover your zone of genius and talks about how we self-sabotage because we reach our upper limit of joy and happiness. He speaks on it in this quote:
“Each of us has an inner thermostat setting that determines how much love, success, and creativity we allow ourselves to enjoy. When we exceed our inner thermostat setting, we will often do something to sabotage ourselves, causing us to drop back into the old, familiar zone where we feel secure.”

Tuesdays With Morrie By Mitch Albom
“So many people walk around with a meaningless life. They seem half-asleep, even when they’re busy doing things they think are important. This is because they’re chasing the wrong things. The way you get meaning into your life is to devote yourself to loving others, devote yourself to your community around you, and devote yourself to creating something that gives you purpose and meaning.”
― Mitch Albom, Tuesdays with Morrie

“If you hold back on the emotions–if you don’t allow yourself to go all the way through them–you can never get to being detached, you’re too busy being afraid. You’re afraid of the pain, you’re afraid of the grief. You’re afraid of the vulnerability that loving entails. But by throwing yourself into these emotions, by allowing yourself to dive in, all the way, over your heard even, you experience them fully and completely.”
― Mitch Albom, Tuesdays with Morrie

What is your favorite quote?

“I’ve never seen any life transformation that didn’t begin with the person in question finally getting tired of their own bullshit.” – Elizabeth Gilbert

This quote made me question what BS I was telling myself back in March of 2020. I said I didn’t have time to make videos, and then quarantine happened, and I had all the time in the world. Now, I can easily make 1 – 2 videos a day.

Key Learnings:

  • You have all the answers that you are looking for, and if you allow yourself to get bored, listen to your intuition, and follow that curiosity, that play will help you to figure it out
  • Expectations are the thief of joy. Getting too fixated on results is where a lot of the suffering lies. Remember that achieving certain results is not what will bring you happiness. Focus on habits, fall in love with the process, and the results will take care of themselves.
  • Find your zone of genius, your ikigai, your flow, your red thread work, because when you find that work where you forget about time, that is the work you were meant to be. Remember the Howard Thurman quote: Don’t ask what the world needs. Ask what makes you come alive because what the world needs is for more people to come alive
  • You are one risk away from changing it all. As We Bought A Zoo said: “You know, sometimes all you need is twenty seconds of insane courage. Just literally twenty seconds of just embarrassing bravery. And I promise you, something great will come of it.”
  • Play is the answer to so many of the problems you struggle with. When you are willing to embrace your fun, nerdy, authentic, weird, strange, quirky self, that is where life is worth living. Your best moments in life are your play moments, so why would you be focused on making more of those.
  • One of the biggest regrets of the dying is I wish I had the courage to live the life I wanted to live and not the life others expected of me. People on their deathbed tell us to be our full selves and stop people-pleasing. Shouldn’t we take the time to listen to their wisdom?