How to Reinvent Yourself and Pivot Your Career (Solo Episode)

It’s not as complicated as you think.

Donald Thompson: Welcome to the Donald Thompson Podcast! Thanks for tuning in.

We’ve had such a great 3rd season so far with amazing guests like Anson Dorrance, Tonya Williams, Jen Hoverstad, Joe Colopy, David Gardner, and more.  And I love having conversations with folks in the Triangle who are inspiring me and others to be great.

But today we’re going to do something a little bit different.

I’ve heard from some of you that you want to hear my perspectives and my advice on how to be a better leader, a better executive, and how to navigate through this storm of COVID-19 and the potential recession. So mom – and everyone else who asked for solo episodes – this one is for you.

You know, one of the things that I have a lot of experience in quite frankly is reinventing myself, right? Like if you look at my career and the different things I’ve done, I’ve started out as a bag carrying sales guy in the tech space in the nineties.

I became a CEO at the age of 36, and so I learned how to manage people, learned how to build and launch, not code, but build technology, product companies. Sell services to enterprise software companies, multi billion dollar companies, and now lead and run a marketing agency. I’m an angel investor, and now I am a certified diversity executive. That’s a lot of different things in the span of a couple of decades to learn how to become proficient. So a couple of things in terms of pivoting your career, learning new skills, reinventing yourself. I think might be a valuable topic to just share a few points of view.

Number one, things are not as complicated as you think. And when you start out with that premise, then you are curious and eager as a learner, not afraid of trying something new. The Google machine is amazing, and will give you lots of articles, white papers, podcasts to listen to about anything you want to learn, and cups of coffee or virtual cups of coffee over Zoom, can be worth millions of dollars to you because successful people in any area endeavor learn to teach people that are on the come up. That are willing to learn, willing to hustle, willing to figure things out.

So what did I do to transcend some of these different arenas? Number one, I’m insatiably curious, and so I learn new things in an in depth way that I’m curious about. So when I started to look in 2015 at the marketing space, the digital marketing space in particular, I was just looking at trends about how people buy.

Saw more and more things being bought over the internet, e-commerce. I saw more and more brands being developed through their digital footprint. I saw more and more people using the term “thought leader.” What is that? I saw the video with the growth and power and the acquisition of Google buying YouTube that video content was very important. So I was like, “Wait a minute, no matter what I do in the future, I am going to need to understand digital marketing and storytelling. I’m going to need the traffic in ideas, and how to communicate those ideas, across different channels. And so that’s why I invested in O3, which now is Walk West, because I understood that pattern of what was coming. And so I immersed myself in this new environment. I read everything I can get my hands on. I learned from the people that every time we were interviewing a developer, a designer, a content strategist, I was learning from every single interview about the ins and outs of this industry.

The clients are great source of knowledge, and over a course of three years, four years, five years, I was able to coalesce my entrepreneur experience, the marketing experience I’ve gained, the team that we were building to now, I’m a very proficient marketer and can create low-cost, high-impact marketing programs, independent of your size of budget because I melded the practices of the traditional markers, marketers with the entrepreneurial heart and hustle, right, of a bootstrap entrepreneur, and now we’ve created some consulting and some packages that are lights out ahead of the rest, but I didn’t let that fear of learning something new hold me back. And then I found people that were willing to teach me. A lot of times, people are looking at pivoting their career, or they’re looking to pivot to be self employed.

I think side hustles are great. It’s a way you can try something new without risking your baseline income. You can learn how to test new ideas. You learn, if you can take your idea and turn that idea into a commercial product or service, and then, when you’re building that new little business, you then know what it takes to, to equate to success.

So if you’re making 50,000, 60,000, a hundred thousand, 200,000. Once you’re making 10, 15, $20,000 from your side hustle, you know it’s just a function of time where you can make more. I also understand, I’m not so big on traditional school, college, MBA – although I employee MBAs and like it’s good, like, but that wasn’t for me, right? But when I wanted to become an expert, or get on my way to being an expert in diversity inclusion, I went to a three day immersive training. I read a 500 page manual four times. I sat for a three hour test two times, passed it the second time. Did a project. So I did the work, the homework, to gain a certification that would be valuable in my new endeavor as a emerging leader in diversity and inclusion, but I was willing to do the work to set the foundation for the new career that I want to create, but I was unafraid. The only thing that I do better than most people is I’m unafraid to do something new and look silly because I know after I look silly the first time, I’ll be better the next time. After I look silly the third time, I’ll be better than the next time. And then what I figured out after the seventh, eighth, ninth time I do something I get better. I get more confidence. I get faster. I get more proficient, but it’s those first sets of conversations. That first book that you read, that you don’t fully understand. That first client meeting that you’re kind of winging it, or winging it a lot.

But being unafraid of doing something new is something that is a superpower and here’s even more important: if you are afraid, do it anyway. My goals have been bigger than my fears. That’s why I’m successful. It’s not that I don’t have fears. My goals are bigger than my fears, so I do it anyway. I sell afraid.

Like, if you think about we’re in the midst of the pandemic, racial unrest, recession, presidential election, and all kinds of other, like then, then your regular life shit, right? Like people’s regular life didn’t stop because of all these macro economic things. So if you got a marriage that’s not perfect, you’ve got kids of any age, right? If you’ve got family, in-laws, job business, just regular life, and then on top of that pandemic, then on top – cause like your mortgage lender, didn’t say free mortgage for a year, right, ’cause we’re in a pandemic, like nobody said, like your bills magically went away, right?

You still have the same life things to do, and how do you push forward through that anxiety, that fear, that uncertainty is my dreams for my life, my dreams for my wife, my dreams for my kids are bigger than the things that bother me. So therefore I keep pushing and keep it moving. It doesn’t mean that success awaits me every day, but progress does. Learning does, and I stay enthusiastic because my failure today will be my strength tomorrow.

And so I don’t live in the failure, even though I fail a lot, even though I make a million mistakes, right? I just feel like it’s really important when you’re thinking about changing anything in your life that you don’t let the fear keep you from dreaming and that you should try things that you’re interested in to see if that interest is a passion. Interest will not sustain you, passion will. You being interested in something, it’s easy to quit. You’ll quit – the moment it gets hard you’ll quit. But if you’re passionate about something, you push through the pain, and usually your success is right on the other side of that thing that you think hurts more than you can take. And then right after that, usually, is your win.

And, you know, I encourage people if you’re in a job and unhappy, figure out a side hustle. If you’re in a job and you think you should be promoted and not, have the tough conversation with your boss, manager, leader and find out why it really is. Maybe you’re not as good as you think you are, and you need to fix that, but you can’t fix what you don’t know.

And so I encourage people when they’re thinking about pivoting, when they’re thinking about starting a new business or thinking about anything that has to do with that next level of transformation, make sure your dream for the future is bigger than the things that you fear. And then you’ll take action. And that really is kinda my, my message, and has underpinned everything that I’ve done. If I’ve met with any level of success.

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The Donald Thompson Podcast is hosted by Walk West CEO, mentor, investor, and Diversity and Inclusion Consultant Donald Thompson.

Music for this episode provided by Jensen Reed from his song, “You Can’t Stop Me”.

The Donald Thompson Podcast is edited and produced by Earfluence. For more on how to engage your community or build your personal brand through podcasting, visit

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