Digital Entrepreneur, NYT Best Selling Author, Thought Leader

The renown name that has taken off in more ways than one — Jenna Kutcher is a force to be reckoned with in both the online and offline spaces. Proving that the term “influencer” can hold many titles, including Best Selling Author, Host of the 80–million–download Goal Digger Podcast, and provoking thought leader who continuously unmasks layers of what it means to be a female making millions, all whilst feeding the baby between zoom meetings. She is a living icon, an inspiration to millions, and one of my all time favorite authentic voices in a billion dollar industry. 

Our interview happened on a misty October morning, in between feeding new born baby Quinn Louise. Her husband entered as if right on cue, while we were moving to our last question and she could finally take a breath. “The baby needs to eat!” He said nonchalantly, as he carefully handed the busy mama her beautiful girl. “It’ll be just a minute! Actually, hold on, you can say hi!” She turned her camera on, and I waved to Drew, or as he’s been sometimes deemed online, ‘Mr. Six Pack’, and admired the beautiful dynamic this couple had mastered. Her pure essence is joy, and she exudes it naturally, while staying true to herself — that is what makes her so relatable, her authentic voice speaks volumes in both vulnerability and strength.

We dove into the obvious question on my mind: what got you into entrepreneurship?

I am a first-generation entrepreneur. I wasn’t one of those kids that grew up watching my parents navigate the world of entrepreneurship. No one in my family ever was an entrepreneur, so this path was a bit unexpected!  

My mom was a nursing instructor and my dad worked at a paper mill so a 9-5 job was the norm for us. While trying to build my first career, I had a big realization that my position in ‘corporate America’ wasn’t secure or stable — in a literal sense, but also in a mental and emotional sense. I gave up so much of my time and energy, working late and coming in early, to know without a doubt that my investment was meaningless in the long run. I figured out that if I don’t take control of my life, someone else is going to control it for me.

That was a huge wake-up call. I don’t necessarily think that I knew entrepreneurship was the ticket out of that world at the time, but I knew that I wanted something that I felt I had more control over. That’s when I started my photography business, which was an entirely self-taught,  challenging, sometimes terrifying, but worthwhile journey for me.

What is the biggest lesson that you’ve learned being your own boss?

I think the biggest lesson that I’ve learned is that it’s so critical that you define your “enough point”. When you leave the world of titles that sound important, bosses who tell you you’re doing a great job, and co-workers who are watching you in the pursuit of your career, you find out that entrepreneurship is really lonely.

 But what often accompanies loneliness is this deep desire to know that what you’re doing makes a difference. Entrepreneurs are high achievers, which means that they will do anything to be successful, which can become their Achilles’ heel of pursuing too much and going too hard, not having things like boundaries, and never logging off. We set these goals, and then we just keep pushing the finish line further and further out. It’s so easy for us to get lost in that hustle and that chase. 

So I would say that the biggest lesson I’ve learned is asking, “What does success look like for me? What is ‘enough’ for me? And where do I plan these moments to pause and celebrate and reflect before moving forward?” There was a time in my business when I would sleep with my computer on the nightstand. I was always available and always reachable.

I think that there’s something so beautiful about logging off and resting. It reminds me of how our computers and our phones need a recharge— so do we. For me, defining those boundaries in my life with my family, my work, and myself has been what keeps my own version of entrepreneurship stable, healthy, and creative.

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 You launched your first book “How Are You, Really?” which became an International Best Seller in the first few weeks of its official launch. Tell us what inspired you to write this book?

When I finally decided to write my book — and people will have to read the end to know how that process started — initially, I was writing a business book. Brainstorming my book, I thought, “I am the host of the Goal Digger Podcast. I am a marketer. I’m an entrepreneur. Of course, I will write a business book!” 

One of the biggest things that I’ve learned most specifically in recent years is that I want to live a life that is enriched with what matters most to me. I want to be present for my life, not missing it while I keep my eyes on the future, because so much of what I have right now is what I used to dream about. There’s gratitude waiting for me at every corner as long as I’m willing to see it.

For me, entrepreneurship has been the ticket to honor all parts of myself: the achiever, the creative, the parent. The person who loves changing the world and the person who wants to just chill at home and color with my 4 year old.

So, the book started to shift away from business into opening up a bigger conversation about that blended kind of life, because I knew I couldn’t be the only one craving it. Of course, entrepreneurship is woven through the book, because that’s a part of my stories, but entrepreneurship isn’t everyone’s career choice. How Are You, Really? is an invitation to stop faking your life, stop going through the motions or giving away your ‘yes’ to the world’s expectations of you… and start figuring out what finding joy in your life looks like for you.

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If you were to write another book, what would be the inspiration for that? 

I loved the entire writing, designing, and releasing process so much, but it wasn’t an easy one by any means. So, this thought came up for me: more often than not, we quit when really we just need to rest. We tend to give up so early, when in reality, we just need to catch our breath and check in with ourselves. 

This is a growing, evolving idea that, in the same vein of How Are You, Really? I believe it will take shape into what will become my next book, whether right away or somewhere down the line. I want to keep bringing to the world a reminder that the pursuit of your goals, dreams, or life vision is supposed to be fun. That’s easy to forget, and I’m excited to weave people back into that truth.

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Photography by Brigitte Billups

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