When You Feel Like You are F---ing Up

Ever have the feeling that you are fucking up?

I know I do. Quite a bit, in fact. Anytime I do something bold or outside my comfort zone, my internal reaction is to doubt or pause.

Here’s a recent example.

I had been working with someone for the last year. He was an industry veteran at a large tech company. He had an impressive set of accolades and yet he was being passed on for promotion. He had a way of minimizing his own voice and then getting frustrated or mad when he was predictably ignored.

As we sat in our coaching session that week, I could feel my own discomfort creep in.

“My manager is at the same level as me; I don’t know why she got the job and I didn’t. I keep getting assigned the menial tasks. They don’t get how valuable I am…”

I could tell he was frustrated, but he wasn’t letting it completely rip. He had a professional veneer that masked his anger from really being expressed even in the safe, confidential container of a coaching call.

I asked: “How can I best support you today?”

He paused and thought about it for a moment. He wanted to come up with a strategy along with some tips and tricks for him to get more recognition and work towards a promotion in the next performance cycle.

“Got it.” I sensed that the conversation was both about his career progressing but also something else.

“Where do you want to start?” I asked.

He led me through a series of strategies he was trying. He wanted to be more vocal in team meetings. He planned to design projects and sell them to higher ups in leadership. He was going to make himself so indispensable that his manager would be forced to recognize how important he was.

None of this sounded inherently bad, but there was an underlying context that I was starting to see. I took a deep breath and took a chance, “Hey, all of this sounds great but it looks like you have a giant ‘Fuck You’ stamped on your forehead and everyone is paying a lot more attention to that than any project or strategy you are employing.”

I paused. It felt bold and direct and yet I could see him recoil.

“I don’t think that’s it. You are not seeing the whole situation correctly. You’re not getting it…”

He stammered and sat there for a few moments. The session ended shortly thereafter and he walked away with a few takeaways that felt tactical and superficial.

As I got off the call, I could feel my own reaction. I swung and missed. My own anxiety started to creep in. This guy is going to quit. You fucked up. You are bad at what you do. My mind started to spiral to all the other times I had taken a chance and it didn’t go well.

4 years into coaching, I have started to normalize this reaction.

I’ve gone through enough cycles of this that I’ve started to see that this is par for the course: that if you are doing anything entrepreneurial or outside of your comfort zone, this voice is predictable to show up.

But why go through this cycle? Why coach or do any work this way?

A senior coach once told me, “Say the thing that would get you fired. It’s the only reason anyone ever hires a coach in the first place.”

While time and more experience has allowed me to add nuance to that training, I generally agree. A great coach has such a level of non-attachment to the outcome, that they are living and dying in the conversation.

It reminds me of a similar idea from Rick Rubin, famed producer of Def Jam records: true creative process should be completely irreverent to its audience. That seems like unconventional advice. Shouldn’t musicians and artists be caring a ton about their listeners’ preferences?

Here’s Rick’s take: you actually don’t know what will land well so you might as well create what you think is best.

That statement is worth unpacking. We have data analytics, prediction machines, and conventional advice around what works and what doesn’t. Whole fields of advertisement and marketing are dedicated to optimizing the right strategy for engagement. So what gives?

I believe what Rick is talking about is any genuine expression of leadership. For you to be a leader (or entrepreneur), it requires doing something different than the rest of the pack. That’s why true leadership is synonymous with creation: it generates something different?—?and therefore valuable?—?than what is predictable to already happen.

If you are really on an edge, there’s no precedent to calibrate towards, and so, you are in a genuine act of creation (a 0 → 1 moment).

So how do you know if you are missing the mark or in the genuine act of creation?

I think there are some clues.

Mainly, a genuine act of creation or leadership will feel like more of You is being expressed in the world. It won’t feel forced or or like you are doing a lot of work to manage or make sense of what is going on. In fact, it may be an act of effortless effort. It certainly is not a reaction to something. It often will feel quite exposing or vulnerable.

Let’s return to the earlier example. I took a risk and reflected honestly what I sensed was in the space. It actually didn’t land well at that moment, but a few months later this happened…

“Hey man, I took some time to think about what you had said. At first, it didn’t sit well with me at all. I was thinking of not showing up to our next session. But I decided to get curious and see if you were right. I could feel some bitterness and frustration I was holding onto. Frustrated at myself for how much time had gone by where I haven’t acted on my dreams. Getting passed on the promotion was just an insult to a wound I was already festering.

I feel lighter now. I forgave myself for how it’s been going the last decade and I made some amends to my manager and team. I feel less rigid and weighed down. I feel ready to take on bold steps this year.”

I could not have predicted this reaction. Sometimes, I will get this type of response. Other times, people will tell me “you are wrong and this is a waste of time.” Trying to predict their response usually is unmanageable. There is no precedent most of the time for people having these types of conversations (afterall, if they were already getting this from a friend or manager…why hire a coach?).

What I have chosen to rely on is my commitment. I have a commitment to reflect the uncomfortable thing. To show up as more Me in the space instead of a caricature of what I think will sell the most or retain clients the longest. In my effort to do that these last 4 years, I have had more unpredictable successes and wins than any sales strategy could have predicted (along with a good number of Fuck You’s).

I have no way of predicting the outcomes, but experience has taught me that me showing up as Me actually works and there’s the side benefit of not having to do all this weird sales and marketing crap that feels ingenuine and transactional.

So to that voice that tells me I am fucking up in the moment, I thank you for your perspective and remember that experience has shown me that authenticity is the only game in town.