Masking the Struggle

I wear masks.

Not the kind you buy in a costume store. Those are uncomfortable, and I’ve never actually aspired to look like Iron Man anyway.

No, I put on the kind we all learn to wear, in order to survive in a rough-and-tumble world.

The “everything’s going great!” mask. The “I’ve got this!” mask. The “I am a rock, I am an iiiiisland…” mask (thanks, Simon and Garfunkel!)

I do realize that navigating through life, and succeeding in business, includes plain old toughing it out. No-one needs to see all of our inner angst. So we learn to close those closet doors and keep that yucky stuff to ourselves.

I also embrace the reality that there is an unavoidable level of projecting confidence and competence into our work surroundings. Who wants to work for a basket case, or hire a whiner, or buy from a timid self-doubter?

Keep a lid on that.

So, we project. Some of that is just plain self-control. Some of it is “fake it ’til you make it,” and some of it is grinding it out and keeping up a brave front.

When we’re working in the fairway of our sweet spot, all feels right with the world. But then, so often we’re hacking away in the rough on our way to a triple bogey:

  • Will I be able to even pay my bills, or draw a salary this month?
  • Why has my main client gone radio silent for weeks?
  • How is it possible to send out 100 carefully crafted emails and get back only 1 tepid response?
  • My strategy sucks. My marketplace sucks. I suck.
  • How come that 31-year old pretender is succeeding and I’m barely scraping by?
  • Am I sane for even trying to keep this ship afloat?

I grew up in a generation transitioning from the tough-it-out manhood of the mid-1900s, to the more touchy-feely 1960’s/1970’s era. Putting on the mask was pretty normal for me, especially growing up in New England (and, in a household of all boys).

For whatever reasons, I felt constantly inferior. I was insecure. In school, there was bullying, as well as “chosen-last-for-the-team” syndrome. The fear, self-doubt, and rage was all internalized, resulting in a state of depression and a constant fear of rejection.

Living meant masking all that struggle (or so I figured).

It wasn’t even a conscious choice. It was a survival mechanism. Grinding it out. Living the mask was…living.

That part’s been getting better over the last 15 years. But, as a solopreneur, I still mask the struggle too often.

As I was writing this  post, I had a coaching call with one of my clients – who is also a peer and a friend. I told him what I was writing and just kinda spilled my guts, because it was safe – he understood. We both have to put on the mask, but we both know we also need people with whom we can drop it.

Obviously, in excess, living the mask can lead to all kinds of ego disorders, as the selfie generation – where projecting perfect appearance is everything – amply illustrates on your social media platform of choice.

Projecting perfection is difficult. Living up to it….well, we are surrounded by 7 billion other failures on this planet.

There are 99 things where I’d be an imposter to project confidence, but there are a few things that I do really, really well for my clients. When I consult, and analyze, and connect, and bring the clarity, I’m the happiest man on the planet. No mask needed.

But there’s a lot of grind, a lot of struggle, and a strong dash of lonely along the way. Because the instinct remains, to hide and overcome, all by my lonesome.



  1. The sense of isolation can be tough at times. I’ve been a solo operator in the same consulting practice for almost 18 years and for the most part my wife has been my go to person for spilling my guts. I’m lucky to have married a very patient woman. 🙂 Lately, I’ve been thinking about connecting more with fellow solopreneurs. What little I’ve done so far has been therapeutic. Thanks for the thought provoking post, Steve.

  2. Bravo, my friend. That impostor syndrome is a bear sometimes. I find it helps to treat that voice like it’s your drunk cousin encouraging you to join him at the bar. Just tell him to shut up and go to bed. He.

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