We had the good fortune of connecting with Stephen Gladney and we’ve shared our conversation below.

Hi Stephen, how do you think about risk?
I’ve taken more risks in my life professionally than anyone else I know. My first job out of college was being a roadie for a rapper. My second job was a commission-only sales job. My third job involved a 25% pay cut and demotion to go work for a startup with 20 employees. At the age of 33, I pivoted to an entirely different career with zero experience and then did it again 17 months later. Most recently, I quit my day job to pursue my side hustle full time. So like I said, I’ve taken a couple of risks.

I’ve always heard the old adage, “With great risk often comes great reward” but I recently realized that I have tended to put far more emphasis on the risk and not enough on the reward.

For example, when deciding if I wanted to completely change careers at the age of 33, I thought about decreased pay, loss of seniority, lack of experience when finding a new job. I worried about having to change my lifestyle for a lower income in my personal life. I worried about having to report to people younger than me in my professional life. I worried that I would never reach the same pinnacle of my career because I was essentially starting over 12 years later. Things like this plagued my thoughts.

What I didn’t think enough about was how much more I would enjoy the work. More importantly, how that would change my life for the better. How I would be so excited to go to work every day. How much I would be learning and growing. All of the new people I would get to meet and work with. Why wasn’t I spending the same amount of time thinking about these things? Weren’t they equally possible and more importantly, equally valuable? I saw a meme on LinkedIn that said “What’s the best that could happen?” and I think that sums it up perfectly.

Humans are hard-wired to avoid risk. It’s how our ancestors avoided getting killed. Needless to say, changing careers probably isn’t going to literally kill you. But your body is still going to fire the same neurons. Becoming aware of this hard-wiring has made it easier to overcome these intuitions, at least for me.

I’ve been fortunate that most of the professional risks I’ve taken have resulted in success. Certainly not all of them. But even in the ones that didn’t work out, I learned and I grew. And if that happens, is it ever really a failure? I think not. Regardless of whatever happens, I know that I don’t have to live with regret. And that’s worth a lot to me.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I went from being a top sales guy to a software developer which is a crazy leap. I wrote a blog post about it if you’d like to hear about how I did it. https://medium.com/salesloft-engineering/yesterday-i-was-the-1-sales-rep-today-i-no-longer-have-a-job-in-sales-3e3aff05cb2e

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
The Local Red’s Beer Garden
So Ba The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
As I’ve entered this new world of entrepreneurship, I’ve been overwhelmed at the support of other founders willing to offer their advice and share their experiences with me. It’s like I’ve joined a secret club with the best (unofficial) orientation program on Earth. And the content. Oh my god, the content. There’s so much content out there for entrepreneurs and on top of it being a big educational benefit, it instills the confidence to keep going. So to anyone who’s ever created any content for founders, thank you.

Instagram: https://www.instagram.com/worksonmymachine/

Linkedin: https://www.linkedin.com/in/stephengladney/

Twitter: https://twitter.com/stephengladney

Facebook: https://www.facebook.com/stephen.gladney.9/

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