Oh No! I Made It!

Dealing with post-achievement anxiety.

In the Seinfeld episode, The Pilot, the character, George, confronts the possibility of real success with a TV show he has co-written and he panics. A lifelong pessimist, he is convinced that anything truly good that lands in his lap is bound to be spoiled post-haste. The thought of “making it” is too much to bear and his anxiety overcomes him as he obsesses over a blemish on his lip, believing it to be a cancer that will kill him just as he is poised to cross over into a new life of fortune and fame.

We laugh at George’s paranoia, but there is truth in this onscreen fiction. Big goals are set and worked towards, but there is a strange comfort in knowing that the odds are against us; if we don’t make it to the finish line, we are in good company because friends and colleagues can relate, commiserate, and commend us for trying.

But to actually succeed? This can be surprisingly stressful.

Success is often coupled with powerful anxiety, brought on by one or more of the following thoughts:

• It was a fluke - I’m here through a mistake, an oversight, a loophole …

• Now that I have achieved this, will people always expect this level of performance from me? Should I expect it from myself?

• Will the other people who have achieved something similar view me as their equal or as a lucky imposter?

• What if I am never able to repeat this kind of thing for the rest of my life?

• This is amazing! It’s all downhill from here. It’s unsustainable.

I have been fortunate in my life to reach numerous milestones and achieve a better-than-average number of the things I set out to achieve. You would think that by now, after having worked for most clients I chased, having books published through publishers I revered, and selling a ‘side hustle’ business to Adobe, I would feel comfortable with success.

Far from it. In fact, it’s completely the opposite!

After I was accepted into the Yale Norfolk art program in college, I immediately assumed I would be the worst artist of the bunch and be seen through from day one. I had to load up on Pepto Bismol, Immodium and Dramamine to calm my stomach and make it out the front door on the first day of class.

(I fit in just fine.)

When my first editorial illustration was published, I was too scared to ask the art director for another job because I assumed he was kicking himself for giving me a chance.

(He hired me a few days later. More freelance worrying here.)

After an important phone call confirming that Adobe was actually interested in an acquisition of my brush business, I cut off communication for a few days with my business manager because I was too scared to take any action at all; I wanted to just rest safely in limbo where I knew the possibility of success existed and I hadn’t yet failed.

(I also had a massive panic attack later that week. It all worked out in the end.)

This pattern continued, and it continues to this day. Every time I achieve a new milestone, I immediately question whether I deserve it, assume it’s a one-off, and start preparing for the inevitable downhill slide.

And there’s more: I worry constantly that people will tire of what it is I have to offer, whether it’s my artwork, my ideas, my teaching, my work for my employer - any and all of it. Another way of putting it: how can I possibly stay relevant?

Take this newsletter. When I started it last December, I set a goal of building a community of 5,000 free subscribers in one year. I’m sitting at a little over 4,000 now and based on current trends, it looks like I will certainly get close to the mark.

Am I happy? Sort of, maybe, but I’m mostly terrified …
Terrified that I will suddenly write something boring or off topic. The quality will drop. Readers will leave in droves. “This isn’t what I signed up for!” They’ll say.

But here is the thing that has saved me every time I felt this way— and I believe it can help anybody out there who is reading this and can relate to what I have written today. If you have ever felt this way about your own achievements, you must always remember this:

Some voice inside you, no matter how small, kept insisting you could succeed. And it was right. And you believed it! Otherwise, you would not have kept going.

It is the only voice that matters. All the rest is noise.

Leave a comment below and share your thoughts.
Take care of yourselves, take care of each other, remember to be kind, and I’ll say, Ciao for now. - Kyle

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Resources

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• Thanks to my pals at one of my favorite Substacks, Animation Obsessive, for sharing this awesome list of free art resources.

• On the work front, I’m proud to announce that there is a new Drawing feature in Adobe Express! I designed all of the brushes and have been working with students and teachers in live demos to get young kids drawing with nothing more than their trackpads to create some mini masterpieces. Hope you’ll check it out - it’s free!

• I partnered with the one and only Morgan Harper Nichols for a promotion for my meditative drawing app, Lines of Zen. Use this link to get a free month of the app through Morgan’s promo code.