The 7 ways I handle fear, doubt, and the crazy inner-turmoil we entrepreneurs face

I have woken up in cold sweats, with the bed literally soaking beneath me. I’ve had nights where sleep just wouldn’t come at all – pushed away by gut-wrenching anxiety. I’ve been pre-occupied with worrisome thoughts that prevented me from getting any simple joys from the nice surprises of life.

These things have plagued me when I was just starting out and completely broke, and even now that I’ve obtained some real success.

And I’m not alone. If you’ve ever taken as big a risk as entrepreneurship, I have no doubt you’ve faced similar, or exactly the same.

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This is a side to freelancing that is very difficult, because no matter what kind of success you reach, it’s always there in some way.

There is a whole industry out there that tries to teach people to conquer these feelings and never again feel fear. It’s all about positivity and changing your mindset. I have to be honest: I think it is all a lie. I don’t think you will ever rid yourself of fear or negativity or doubt. I think fear is what has kept our species and millions of other beings on this planet alive through the ages. (I do believe we can become more positive and resourceful, but that’s another topic for another day.)

So this blog post isn’t about how to “cure” yourself or become a glowing rainbow-unicorn of positivity. It’s about how to accept these things as part of your life, experience them, and still live a meaningful life anyway.

So when these feelings rear their ugly, bloody head, here’s what I typically do.

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First: I face them.

I’ll spend some quiet time with my feelings, because sometimes they carry an important message for me. They nudge me in a new direction, or open me to sides of myself I didn’t even realize I was closed to. They remind me of things I’ve forgotten or teach me something new. When I’m closed off and hardened by stress, they force me open.

I don’t try to push them out or put up a wall. I let them in and let them do their worst.

Often, the thing that makes them go away is the one thing you never want to do: face them head on.

I believe this practice has made me a better artist, too. It’s made me think and feel more deeply and not avoid things that are uncomfortable. That depth creeps into everything that I do. Like my old wrestling coach used to say (or scream):

You have to get comfortable with being uncomfortable.

He was talking about the pain we endured through hundreds of pushups and squats and sprints, but it turns out it’s great advice for life and freelancers too.

Second: I do the thing I’m avoiding.

Sometimes I realize my anxiety is caused by me having put off some action or confrontation. Maybe I’m scared to write a certain email, or have a certain conversation, or a task has felt overwhelming so I keep setting it aside.

If I realize my fear is caused by something that I can do, I do the thing as quickly as I possibly can.

Sometimes I realize it’s because I’m doing something that I shouldn’t be. When that’s the case, I stop the thing right away, and if need be, apologize if I feel it may have hurt someone. Sometimes I don’t even realize I’m acting a certain way until anxiety wakes me up about it in the middle of the night.

Third: If that doesn’t work, I try to laugh.

I’ll put on a show like “The Office” or anything that usually gives me a smile. Because if I’ve handled the feelings for a while and tried to work through them, but they’re not keen on being worked through, then I’ve got to free myself in some way.

Nothing frees up anxiety like laughter. It instantly splits it open like a can of tuna and it starts to fade.

Fourth: I talk to someone who will challenge me.

That’s usually my partner in business and life, Louisa.

There are friends and loved ones who will simply comfort you and tell you what you want to hear, and there are those who will challenge you and push you to see your situation in a new light.

The latter is the kind I’ll talk to first:

  • I want to understand what’s giving me such a hard time.
  • I don’t want to be let off the hook so easy.
  • I want to learn and grow from it so I can become better.
  • I want someone to tell me what I need to do or what I need to stop doing that I’m too close to the situation or stubborn to see myself.

Fifth: I talk to someone who tells me what I want to hear.

That’s usually my mom.

She is quick to remind me of how much I’ve accomplished and how proud she is of me. She says it’s amazing how much I’ve accomplished in my 26 years. She tells me what she was doing when she was 26, which was what most hippies were doing in the 70s. She tells me stories of how I was as a kid or an infant and we laugh.

Sixth: I go to the gym.

Sometimes you can pummel those tough feelings right out of you with a good workout. There’s a reason they say the gym is like therapy.

Seventh: I throw out the drawing board, and try something new.

If my six other remedies won’t work, it’s time to get creative. But the mind is an amazing thing. Usually an idea of what I need to do has been there all along, but I’ve just been avoiding it. But when I finally give up and take the idea to heart – the anxiety almost always goes away in an instant.

Sometimes that means hitting something, or taking a walk at 2 in the morning, or writing, or drawing. Sometimes it means cooking or cleaning or looking at old photos.

By this point, I’m open to anything. It’s time to try something else. If you can calm yourself just enough to listen to what’s going on inside, I’ve found that usually that something else will present itself. Then you just have to do what it says.

How about you? How do you deal with these things?

I’d love to hear your thoughts.

Because if I were to come up with an eighth tactic, it would without a doubt be learning from others and how they handle it all.

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Millo Articles by David Tendrich

David Tendrich is the co-head of creative agency Unexpected Ways, as well as the co-founder of Reliable PSD: the first-ever PSD to HTML & PSD to Wordpress service run by designers, for designers. He co-runs his companies from Portland, Oregon with his lovely wife and biz partner, Lou Levit.
Read more from David.

  1. Great post, mate. Felt I was reading a story of your life. Since these are some great tips coming from an experienced person, ill hold on to it.

    As for me, when I am in doubt, I just look back and think about worst things I have survived and things that made me what I am today.

    And when I am in Fear, I just face them heads on because there is other way around.

  2. Danielle Zuckerman says:

    I needed this article so badly this week, thank you thank you David!

  3. I’m a worst-case-scenario guy, so I’m constantly riding the fear rollercoaster. There are times when I become so incapacitated by fear that I have no choice but to face it. What I often do is start with the worst-case-scenario and work back from there. What’s the worst possible thing that could happen? Would I survive it? OK, what’s the most likely thing to happen? Can I survive that?

    I see a lot of people paralyzed by fear, “living” a life of safety to avoid being uncomfortable. I think the important thing is to recognize a balance between taking risks and being reckless. I think you hit it on the head; fear is what has kept our species alive. It’s healthy.

    Thanks for sharing the article. This is definitely one worth saving.

    1. David Tendrich says:

      “I see a lot of people paralyzed by fear, ‘living’ a life of safety to avoid being uncomfortable.”

      Bam! Mic drops, Patrick walks off stage.

      So well said. So glad you took the time to leave this comment, thank you.


  4. Judith Brieger says:

    Terrific article indeed. Thanks so much for sharing. I have found some interesting insights when I feel fear getting the better of me in the book “If The Buddha Gets Stuck”. Some interesting teachings from Buddhism on how to sit with fear – how to deal with it head on instead of trying any coping mechanism we may invented or adopted over time. Again, no holy grail there but sometimes just knowing that we all go through those phases is a helpful reminder.

    1. David Tendrich says:

      Hey Judith, thanks for your kind words 🙂 That really is a great reminder. Those feelings can be so isolating.

      I think they call it “sitting”, when you just spend time with what’s going on inside you and try not to analyze or judge it. That practice has really changed my life over the years.

      Love that book title. Amazon-ing it right now 🙂


  5. Dan Coggins says:

    I’d recommend a book by David Burns called “The Feeling Good Handbook”. It helps me think through the crazy distortions that I’m putting on bad outcomes I *imagine* will happen if some project “goes south”. In 15 minutes, it takes my anxiety down to 10% of what it was. It is an amazing resource that helps me with what I’ll call “emotional hygiene” around projects and clients. LOVE IT!

    1. David Tendrich says:

      Wow, that sounds amazing. I will definitely check it out 🙂

      Thanks for sharing.

  6. April Greer says:

    Excellent post, David!

    I’m firmly in your camp – face your fears, your doubts, and your emotions. That quiet reflection time is priceless and has the additional benefit of making you more honest with yourself in the personal arena as well. (If you thought freelancing was hard, try love, right?!)

    My favorite saying regarding this goes, “Don’t let lizards turn into dragons.” By dealing with emotions head on (even if it’s acknowledging that they’re absurd and determining how to quell irrationality), you prevent them from escalating into much bigger – and often compounded – problems later.

    1. David Tendrich says:

      Thanks, April 🙂 That means a lot.

      That’s a great saying. What do you do about those invisible lizards though, that you don’t even know are there? O.O I seem to have quite a few of those crawling around lol 😉

  7. Freelancing can be very frustrating. To the point you consider quitting and going back to a 9 to 5 job. But, you need to remember being your own boss will always come with its own set of problems and bad days. Keep this in mind and roll with the punches.

    1. David Tendrich says:

      Very true. And even when you’ve built something really solid, somehow it always feels like it could get swept away in an instant, as irrational as that might be. In the back of my head sometimes I catch myself wondering…

      “Maybe I could be a barista if this whole thing doesn’t work out” lol 🙂

      But deep down I know that’s never going to happen 😉 A part of me is just always on guard. Maybe that’s nature’s way of keeping me safe. Who knows? 😉

  8. Michelle Fontaine says:

    You have me giggling as my bread and butter clients right now are life coaches. 😉 My big fear is the holiday season when work gets really slow!!! I don’t really enjoy the holidays because of this anxiety, and wish I were as mega positive and peppy as my clients!

    1. David Tendrich says:

      Haha! That is great.

      Sorry to hear about your holiday-time anxiety 🙁 I hope you can find some peace in these next few weeks.


  9. Brian McKeown says:

    Greetings David, that was a really terrific article on fear and self doubt. It seems to be part of the creative person’s make-up, always there in the background, only bursting through in times of stress.
    It is an awful sensation when it breaks through, gut wrenching, devours hours of valuable time threshing around trying to get your feet back on solid ground. You are correct in the ways you suggest dealing with it, reach out to friends that you can talk to in confidence. I try not to burden my better half with it, I go to her for a cup of sunshine and a laugh. Oddly some of the best restarts I have had are from really good clients, that I produce work for and that not so rare thing! really appreciate your creativity in solving their business communications problem or task. They seem to get that if you are that sensitive to every nuance of the wording of the brief, so you can come up with an original winning concept, you may sometimes travel through the dark valley to get back in the sunshine. It will pass and you forget it until it makes it’s unwelcome return visit, but again it will pass. Some of the people who commission work, i feel, figure that is part of what makes creatives, a bit like theatre – dialog, action, farce, regret, triumph and wisdom. Maybe not always in that order.
    Best regards,
    Keep calm and carry on!

    1. David Tendrich says:

      Hey Brian,

      Very wise words, my friend 🙂 That’s exactly how it feels, too, like you’re not even standing on solid ground.

      You know, come to think of it I’ve had similar experiences, where really grateful clients who really appreciate you restore your faith in things. It’s crazy how in your head you can be so convinced of all these awful things, and then one happy person who likes you comes along and you realize how absurd everything you were just thinking really is.

  10. love these tips David, thank you!

    1. David Tendrich says:

      Thanks, JMH 🙂 Means a lot that you took the time to say that


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