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Thriving as an Entrepreneur in the Digital Age – 5 Lessons from Dr. Sherry Walling

Thriving as an Entrepreneur in the Digital Age – 5 Lessons from Dr. Sherry Walling

Dr. Sherry Walling offers a unique perspective on entrepreneur burnout.

As both an accomplished clinical psychologist and the spouse of a serial tech entrepreneur, she’s combined insights from both roles and developed a much-needed resource called ZenFounder.

On a recent Technology for Mindfulness podcast, our founder Robert Plotkin interviewed Dr. Walling to learn more about her work.

They chatted about entrepreneur stress, how it’s made worse by the frenetic pace of technology, and her recommendations for founders (and their partners).


Entrepreneur Burnout – Discovering an Unmet Need


So how does a clinical psychologist go from treating PTSD in combat veterans to helping entrepreneurs manage the stress of starting their own business?

Surprisingly, they have a lot in common.

“I spent the first half of my career working with people who had really intense jobs. Often in the military, sometimes first responders, physicians that worked in the ER. (They had) high stress, high intensity, high levels of trauma.”

Throughout this time, she was married to her husband Rob Walling, who has founded and sold several technology startups.

“I kept seeing the overlap between the folks I worked with in my day job and the kinds of mental health concerns that the entrepreneurial tech friends (in my husband’s circle) were having.”

Dr. Walling began to realize that this was a conversation that people were desperate to have. As she delved deeper, she found that research backed up the burnout crisis among the entrepreneur community.

According to a seminal study by Michael Freeman, entrepreneurs are 50 percent more likely to report having a mental health condition.

This raises many questions:

  • Are entrepreneurs adapting to an existing mental health condition by pursuing work outside the normal 9-5 world?
  • Or are their struggles a consequence of the incredible difficulty and inherent loneliness of a startup?
  • Have entrepreneurs always been this susceptible to burnout or has technology contributed to the crisis?

While this is a difficult issue to untangle, Dr. Walling saw an unmet need and stepped up to help.

ZenFounder was born.

entrepreneur burnout
Her business now offers consulting services to solopreneurs, startups, and existing businesses as well as resources like the ZenFounder podcast, her book The Entrepreneur’s Guide to Keeping Your Sh*t Together, and a relationship course Date Night Bootcamp.

Five Lessons to Survive, Thrive, and Connect as an Entrepreneur


During the podcast conversation, Dr. Walling offered listeners a few lessons on how to move through the challenges of being an entrepreneur.

1. Don’t Play the Comparison Game

For entrepreneurs, who are constantly trying to prove themselves – to investors, customers, partners, family, and themselves – social media can be mentally crippling.

Walling says, “I do think it’s a bit of the shadow side of our technological advances. And I’m not anti-tech by any means. But we now have clear data that links social media platforms like Facebook to depression.”

She cautions entrepreneurs to think carefully about how social media shapes how we see ourselves and our lives. It’s a continuous barrage of notifications and information, which is unlike anything we’ve had to manage before.

Being conscious of this influence and reducing your exposure is the first step.

2. Define Success On Your Own Terms

To help move away from comparison, Dr. Walling warns against using busyness as a metric of success.

“It’s a shallow metric,” she says.

With the “always on” pace of today’s technology, many entrepreneurs wear busyness like a badge of honor. However, it’s not an indicator of success. It doesn’t connect to value.

Instead of hiding behind a busy schedule, ask the hard questions. Questions that may feel uncomfortable at first, but get at the heart of success:

  • What work are you doing that’s meaningful to you?
  • What are you excited about?
  • How are you growing?
  • Are you happy?

Remember why you’re doing this. When you know what matters, the busyness of your competitors on social media loses its meaning.

3. Make Sure Your Schedule Reflects Your Values

Once you get clarity on the questions above, your next step is to take a hard look at your schedule.

Empirical research has shown that if you’re suffering from burnout, there’s likely a mismatch between what you’re doing every day and your core values.

Dr. Walling suggests walking through each of your daily responsibilities and asking “why are you doing this?” and “is the benefit worth the cost?” Not from a financial perspective, but a mental cost.

When entrepreneurs show resistance, she shifts the language from “soft” words like happiness to very practical terms like productivity.

In other words, by analyzing your emotional response to certain tasks or obligations, you have the ability to shift your work and “optimize” yourself. You can be the best version of you.

4. Don’t Underestimate Entrepreneur Burnout

With burnout being so common among the startup community, there’s a tendency to diminish the dangers.

Yet it’s a recognized condition by both psychological and medical fields. Prolonged stress causes real neurological changes in your brain.  It can lead to serious consequences including impaired memory, compromised immune response, inability to regulate emotion, and even heart disease.

The good news is that the brain has the ability to reset through everyday mindfulness techniques you can incorporate into your work life to reduce stress.

Walling encourages entrepreneurs to seek help if they begin to experience the three hallmarks of burnout:

  • Physical and Emotional Exhaustion
  • Cynicism and Detachment
  • Ineffectiveness and Feeling a Lack of Accomplishment

Burnout can cause serious harm to your business – but you could also lose even more important assets – your relationships.

5. Recognize Relationships Need Extra Care

It was Dr. Walling’s own experience as the spouse of an entrepreneur that helped her understand the unique challenges for people in relationships with a business founder.

Whether intentional or not, the partner of an entrepreneur goes through many of the same emotional ups and downs. Not only that, it can be hard to make time for a relationship when so much of their time is invested in a new business.

Every relationship takes work. Being an entrepreneur (or being with an entrepreneur) can make relationships harder.

By recognizing this, you can be more aware of how your emotional state affects your partner’s. And since you’re reviewing your schedule (see lesson 3!), make sure your calendar reflects the value you place upon your relationships.

If you need help navigating the world of entrepreneur relationships, Dr. Walling recently developed the Date Night Bootcamp. It’s a set of videos and conversation guides focusing on emotional connection and communication, both of which must be firmly in place to endure the roller coaster of entrepreneurial life.



With all its ups and downs, Dr. Walling still feels that the entrepreneurial life is a wonderful privilege. Her goal is to make the experience sustainable, healthy, fun, and meaningful.

Want to learn more?

For more insights on how to avoid entrepreneur burnout:

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