Empathy for the Entrepreneur

Reconciling your audacity and your self doubt

Treat therapy like a business opportunity.

Over the past few weeks I have read scores of articles on Forbes, Inc, Entrepreneur, and dozens of blogs about how entrepreneurs, especially, are struggling with anxiety and depression. Just under the tough exterior of a founder runs a river of doubt, questioning, and issues of self-worth.

I believe this is why entrepreneurs do what they do: audacity is the twin of self doubt. If you understand that both aspects of your personality are valid, and that both characteristics of you are inherently linked to your unique contribution, then both your boldness and your doubt are powerful in their own way. It is this potent mix that requires nurturing.

Therapy: mentorship for your soul

A therapist can help guide this journey of resilience. Therapy is aboutvaluing both the confidence and the self-doubt, seeing their place in the scheme of things, and figuring out where to go from there. Entrepreneurs don’t need to go it alone. In fact, a therapist is like a mentor for your soul.

Making the time for mental health is a good way to start sorting out your life, your work, your priorities, and to fix goals that you can actually meet.

Therapy is respite from the posturing of ‘foundership’, while maintaining your strength and respect. A good therapist will make sure of that. You will be supported.

To struggle is a normal part of life.

The struggle

Life is always throwing something at you. Just beyond the edges of your business life, the real world is going on. Sometimes things happen in your life that affect you and your work. Grief does not go away. Trauma only lessens, it does not leave. If you survive and thrive, then you develop into someone you didn’t know you could become. Time and pressure and worry can be potent change-agents for entrepreneurs. They are not sloth and laziness (as the stigma suggests) and they need not drag you down. These struggles are the marks of the strongest people in the world. This is entrepreneurship: the pursuit of something, despite everything.

As a therapist, I believe that people who are truly living a mindful, well-considered life are reinventing themselves and making minor adjustments because this type of examined life requires reinvention, re-attunement, and the constant seeking of contentment and peace despite the curveballs of life.

Even in business, the only struggle that matters is the struggle against the self.

Know your values

Learning your values is a tough process, but it’s a worthwhile one. Your values will point to your interests, your path, and will help you recognize that ‘feeling’ of what you want your life to be like. Not taking the time to truly understand your strengths (and by extension, your areas of disinterest), can lead to anxiety, stress, and a sense that your work is not as fulfilling as you would have liked it to be.


Being your authentic self means you are more likely to be fulfilled. You will be able to describe your needs to others, and you are more likely to be able to identify what you want and what you do not want.

If you ‘package’ yourself and your personal brand in a certain way that is authentic to who you are, then you’re most likely to be recognized for being just that: you will get the right opportunities, and you will have the ability, the language, to articulate what works for you.

Seeking meaning

I believe that in order to live a good life, you have to seek meaning in everything you do. That includes working with meaning. Having your own business means you owe it to yourself to infuse purpose into your actions and to think beyond your product or service and look at the bigger picture. Whenever possible, give to charity, support your family, and set aside time to be with the people you love — ultimately, they want your time, not your money. Think of it this way: is your work a good enough reason to leave the people you love every day? Are you coming home knowing you are one step closer to doing work your grandkids will be proud of?

“The good life is a process, not a state of being.” Carl Rogers

Whose goals and dreams are these?

Set a vision and set goals that you can commit to, that speak to your longterm vision, and that are true to your authentic self. Revisit the vision and goals when you get side-tracked by cool ideas or partnership opportunities that sound great but may not serve you well in the longterm.

A dream deferred

The well-being of a person is not just dependent on financial success, but also a host of other things: relationships, physical health, ability to balance family, work, and time for yourself. A lot of entrepreneurs (especially younger ones) say, “Oh, I’ll deal with all that later. First, I need to figure out this product/service/close this deal…” And when I circle back to them months later, they may have created a cool product (or not), but they are still suffering: unable to enjoy what they have built. That’s unfortunate.

In business school they talk a lot about how to not defer the siren call of entrepreneurship. To not trade in a dream for a life of discontentment. Well, this still holds true for those who embarked on their dream: don’t defer contentment. Take the time to be content. If not now, then…when? Is your dream worth it if you can’t ever be content?

Isn’t it THE dream to be content* with your life?

*Note that I didn’t say ‘happy’ because the way I define contentment, it is a deeper, steadier feeling: it does not exclude sadness, rather, someone who is generally content has space in their life for uncertainty, and has a healthy way to express their feelings.

Just as you struggle through the vicissitudes of a start-up, so should you be struggling with yourself. This is a normal part of a healthy life. Having a therapist helps to guide that process. It’s like kicking around in a pool, versus taking a lesson in swimming. Just a little guidance can help propel you. Knowing you need guidance is half of the struggle. This is mindfulness: to be present with yourself.

“The more still, more patient, and more open we are when we are sad, so much the deeper and so much the more unswervingly does the new go into us..” Rainer Maria Rilke

Set boundaries and let stuff go

Focus is a huge part of well-defined personal success. Do one or two things well. Do them with your own flair and panache. And let go of all the stuff you know you won’t really ever do. Be aware of what is on your to-do list and what just sounds like a good idea because everyone else is doing it. Do you really need to go to that conference just to be seen? If it doesn’t fit in with your value system, cross it off your list for good. If you feel guilty for not measuring up to others’ or not seeming as busy, then talk to your therapist about it. Sketch out with him or her what values you have and where those values come from.

Be yourself in a world where the true ‘self’ is undervalued. I just wrote an article on the fear of missing out. Our new, technological life is filled with the inauthentic: doctored photos, a focus on fun instead of reflection, alarming unaccountability, and the pursuit of values that don’t always make us feel good.

Use your intuition and move in a direction that makes sense to you and which resonates with your particular goals. This doesn’t mean choosing the easy route — on the contrary — it means listening carefully to your inner guide and making the decisions that are right for you in the longterm.

Fear, uncertainty, and the other F word

Young entrepreneurs have the impression that everyone is doing better than them. That is patently not true (see imposter syndrome). And then there’s the other F-word: Failure. Failure is a huge part of business — it’s a big part of life! What most seasoned entrepreneurs know is that failure is the flint that ignites success. But if you treat failure like a mistake instead of a sort of blessing, then you douse the flint. The creative spark slowly dies. You feel ashamed of failure, when in fact you should be writing about it, talking about it, learning from it, and regrouping. It’s easier said than done because that requires a lot of soul searching. Part of that process is also being able to identify people around you that allow you to fail.

Fear can feel like a living death. You can’t tolerate fear alone. Fear dissipates somewhat if it’s spoken out loud. It’s an invitation to explore. Uncertainty hates firm ground and a voice. Finding a group, an empathic listener, a trusted companion, can help.

Sometimes you survive (and that’s success)


As entrepreneurs, we feel the need to always be doing something amazing, something big, to have a plan, and to be taking action. But what about the permission to do none of those things? If it’s permission you need, I’m giving it to you. Take the time to cultivate who you are to replenish the stores: go out in nature, see some art, have a chocolate croissant. We all have voices that tell us what we should or ought to be doing. Study those voices closely: do they come from a place of bolstering you, or of making you feel insecure?

Don’t compare yourself to others

If you feel woefully unprepared, undereducated, and you’re waiting for *that moment* where you’ll magically know everything — well, that moment is not coming. You are as prepared now as you’re supposed to be. Know the difference between what you realistically need to improve and what is already okay. Perhaps you feel like everyone else is more qualified. Don’t judge other people’s qualifications when you don’t have insight into their flaws or deeper issues. Emotionally intelligent people work on themselves, then set boundaries between themselves and others, and try to stand forsomething.

You are enough.

Focus on one thing — don’t be distracted by all the things everyone else is doing. They are not you. And you are not them. And that’s fine.

Telling your story in therapy

Being under pressure can bring out old wounds. We often fall back on old habits that may no longer be serving our needs. For instance, stress may induce us to start smoking or drinking as a coping mechanism because we don’t want to admit to the real reason we feel bad. Understand that from a cognitive perspective, you believe the story you weave for yourself. An authentic story does include pain. And telling a story that is inclusive of our shortcomings is a great strength. Often, being authentic is about telling a cohesive story that connects your real experience, your real interests, and your work with your deeper, core values — your ‘why I do this’. Therapy is a helpful place to weave this story in an authentic way that makes you feel like a whole person.

“Knowing yourself is the beginning of all wisdom.” Aristotle

How a therapist can help

Therapy is a place where you can confidentially work through your struggles: whether they are about stress, managing your emotions, balancing your life, or about overcoming trauma and regret. In individual therapy, your one-on-one work could be about setting goals, it could be about learning listening skills, or about being listened to. It could be about your creative process, dealing with your co-founder, or figuring out how to distribute your new product. It could be any of the things I’ve listed above. Or it could be something else entirely. Whatever the issue, therapy is your safe space.

Treat therapy as if it were a business opportunity.

Going to therapy is a chance for strength, mental clarity, to dispel stress, and learn tools to tackle those big questions that arise in your work and your life.

Just as you would enlist a mentor or take business meetings, make time in your schedule for therapy, and use it as a means to engage more deeply with yourself — self-reflection makes a better entrepreneur.