This Goal Digger Can Help You Tap Your Own Potential

Jenna Kutcher is crystal clear on what she wants in life, and she’s figured out how to get it.

This 30-something Minnesota mom treasures her at-home time with her husband and two little girls. She does the things other moms do—grocery shopping, struggling with nap time, keeping tabs on house repairs, cleaning up spilled Cheerios from the kitchen floor.

For Kutcher, there’s nothing in the world more important than the happiness and wellbeing of her family. She clearly embraces the adage that “no other success can compensate for failure in the home.”

Stay-at-home Kutcher is also one of the best-known social media influencers on the planet.

After buying a $300 camera on Craigslist, Kutcher became an award-winning wedding photographer. She loved that. But she dreamed a different dream and decided she preferred working from her cozy craftsman home in her yoga pants. To provide practical advice to other women entrepreneurs, she launched a podcast called “Goal Digger.”

That podcast, which now reaches millions of subscribers around the world and is the hub of her seven-figure business, follows a live workshop format. Kutcher dispenses practical advice on a range of subjects like getting more done in less time, building your brand, using Pinterest to promote your business, and growing your email list by thousands of names each month. She also hosts prominent guests on the podcast and promises listeners that they can train with the experts on how to dig in, do the work, and tackle their biggest goals along the way.

Yes, that all sounds ambitious. It is. But judging by the relevant metrics, everything is working out A-okay for this work-from-home mom in yoga pants: she’s hosting the world’s number one rated marketing podcast with 570+ episodes and more than 65 million downloads.

Although most of Kutcher’s content focuses on how to be a successful entrepreneur, she also serves up commonsense, why-didn’t-I-think-of-that advice on managing life in a world consumed by busyness and insecurity. While many influencers project picture-perfect lives of not a hair out of place, Kutcher addresses her followers with refreshing doses of realism. In one recent Instagram post, featuring a photo of her with one of her young daughters on the beach, Kutcher commented that her children don’t care about the cellulite on her legs or her loose tummy that was once their home. She wrote: “When people ask them about their mommy, they don’t reference the number on the scale, the size on the tag of my pants, the wrinkle above my lip when I smile, or the stretch marks lining my body. They talk about how mama splashed with them, chased them, held them close, and squealed with delight.”

Kutcher carries that theme into her new book How Are You, Really? She writes: “Our bodies aren’t personality Tupperware, waiting to be shoved and stacked and squeezed into smaller spaces. Our bodies are soft, uniquely shaped, hairy-legged beings that need wide, vast space to birth dreams. To live long, to leave legacies. To do the work that ignites us in any and every way. To rest and enjoy what we’ve earned. To heal. To experience life.”

Have you noticed? Some people are simply wise beyond their years. Jenna Kutcher is in that club. She rejects the hustle harder mentality and still gets interesting and important things done. In How Are You, Really? she explains how to live a rich life outside the quixotic “having it all” cliché.

Rodger Dean Duncan: The notion of “golden handcuffs,” you say, is not just about a career with too-good-to-pass-up benefits. It also applies to what might be called consensual entrapment in other areas of life. What examples of that do you see, and what’s your advice for breaking free?

Jenna Kutcher: This notion of “golden handcuffs” can show up in our lives and be easily confused for gratitude.

Gratitude in itself is a beautiful practice, but reminding ourselves to be grateful, even when we know something isn’t the right fit for us any longer, can keep us tied to jobs, relationships, and various life situations longer than we should be.

Gratitude can be a tool to keep us going, but we can also use it as a means to stay stuck. If you are being reminded of the “benefits” of something, check in with yourself and ask yourself if those benefits truly add value to your life in a meaningful way. If the answer is “No,” then it’s likely time to release the handcuffs and move forward.

Duncan: You quote Maya Angelou as saying that “making a ‘living’ is not the same as ‘making a life.’” Why do so many people seem to have missed that memo?

Kutcher: In our productivity-focused society, it’s easy for us to create lives around our work instead of creating work that supports our lives.

As entrepreneurs, it’s not uncommon to abandon our 9-to-5s only to find ourselves working 24/7. Our achieving natures measure our worth through our output and the obsession with efficiency has us working harder just so we can save time to work harder yet.

Duncan: You subscribe to the notion that big dreams happen by going small. How does that apply to entrepreneurship?

Kutcher: Your success as an entrepreneur is impacted directly by your level of confidence and your confidence is impacted by your ability to follow through.

When we take impossibly small action towards our goals, we build up our belief in ourselves to follow through, to get results, and to continue on. Small actions build the muscles required for the big impact, so I encourage people to start small and build your belief in yourself on the path.

Duncan: What are the top two or three most common mistakes made by entrepreneurs?

Kutcher: Number one is believing that things happen overnight. I’m an example of “over-decade” success. Slow growth equals deeper roots, so work in a way that ensures longevity and keep a pulse on how you’re enjoying the journey.

Another common mistake by entrepreneurs is quitting, when really they just need to rest. Entrepreneurship is a lot of things, and one of them is exhausting. A lot of times when people quit, they should have just taken a step back, taken a nap, and rested to come back rejuvenated.

Duncan: What role does intuition play in the success of someone who’s working to build a business?

Kutcher: In a world focused on systems and strategies, intuition is everything. In fact, I’d go as far to say it’s the most underutilized skill in the field. It’s the difference between forcing something and finding flow.

Your gut is guiding you. Listen to it and trust it. When we trust in our knowing, we stay aligned with our truth and it impacts how we show up in life, in business, in relationships—everything.

Duncan: Most people can list a lot of the negatives of the Covid pandemic. What do you see as some of the pandemic’s silver lining—things people have discovered about the art of the possible … or maybe the art of the preferable?

Kutcher: As someone who started, built, and scaled my career from towns with populations of fewer than 10,000 people, the pandemic verified my hunch: entrepreneurs can reach people no matter where they are with a little Wi-Fi and some technology.

I’m grateful that the ability to connect while living and working remotely became more mainstream because there’s nothing I love more than connecting with humans digitally and then getting back to life in the flesh with the ones I love most! Not having to travel for work and sleeping in my own bed and being with my babies when they wake is definitely preferable for me in this season of life!

Duncan: You seem to go out of your way to promote self-acceptance. Aside from the obvious influence of advertising and other media, what is it about our society that encourages people to chase unrealistic (and even harmful) visions of themselves?

Kutcher: There’s a line in my book that I think about every day. It says, “How you rise up to your battles is linked to the kind of warrior you believe you are.”

While the world is telling us that we’re not enough or we don’t measure up, it’s impacting our ability to simply show up and sabotaging our self-belief that we are equipped to make an impact. A lot of our inner dialogue has been adopted from headlines targeting us to get the next quick fix. But we don’t need to be fixed. We need to start loving ourselves as whole, imperfect humans who are equipped to make a difference.

Duncan: You write: “Instead of gaslighting your own feelings, or punishing yourself for having a negative thought in the first place, your challenge is to redirect that energy back to what you have learned is true about you.” What does following that advice look like in terms of observable behaviors?

Kutcher: As someone who practices meditation, I’ve recognized the gift of awareness—of simply noticing. Noticing our thoughts, our feelings, and our beliefs is where it all begins.

So much of our lives is narrated by these inner dialogues that we’ve borrowed from other people without questioning or noticing where they came from or if they are true. Once we notice it, we can release or redirect a thought, then rewire the brain with a more appropriate narrative, creating a story loop that we want to replay again and again in the future.

Duncan: Studies show that the people closest to you shape your interests, your outlook, your habits and, therefore, your outcomes. So, where can someone turn for help if living in a family of people who offer little encouragement to chase dreams?

Kutcher: Most of the time, we find that the people closest to us are actually the last ones to support us. Isn’t that wild? Part of that is because they might see us changing and growing while they might be staying the same, and that sort of change is scary and sometimes unrelatable. It’s important, then, to seek out a supportive community—whether it’s through Facebook groups, organized meet ups, or chats with fellow creatives in your town or city. Having people with you on the journey is imperative to enjoying the ride!

Duncan: There’s a lot of talk these days about how people can “reimagine” or “reinvent” themselves. What do you see as the keys to a person’s positive transformation?

Kutcher: First, get super clear on what success means to you! So often we focus on what success will look like, but I want for you to envision what success will feel like—for you. Maybe there are aspects of your identity you need to leave behind in the pursuit of who you are transforming into.

Next, I want for you to start small. Build up your confidence through tiny actions that move you towards the version of yourself you are striving to become. With each bit of progress, your confidence will grow!

Lastly, check in with yourself often. Does the pursuit feel good? Are you enjoying the journey? Are you enjoying your life? Asking yourself, “How am I, really?” will keep you awake to your progress and excited about who you are becoming.

Duncan: What question do you wish I had asked, but didn’t … and how would you respond?

Kutcher: Does this feel good? It’s easy in entrepreneurship to pursue the shiny things, the things that look good and sound impressive. But those things often leave us feeling exhausted, burned out, or out of alignment. The destination is just a moment, but the journey is our lives. If we want to do work that matters, if we want to be fully awake to our lives, we have to check in with ourselves often and get quiet enough to answer the harder questions.