Insecurity is a superpower

Time for a little founder's journal.

Every entrepreneur has insecurities.

Like 100% of us.

But for many reasons we don't choose to address them, which means we don't spend the time working on them.

And there's good reason we don't share our insecurities.

The world doesn't reward us sharing them & incentives dictate actions.

There's little upside and there's a lot of potential downside.

We fear that sharing our insecurities will make us look weak or unqualified when talking to VCs or potential investors.

Especially when an investor is considering us against 50 other potential investments and 50 entrepreneurs who likely haven't shared their insecurities as well.

We fear that sharing our insecurities will make us look unconfident or unqualified to our employees who trust us with their livelihood.

We tell ourselves this story that we need to be a rock for our employees, this center of gravity that keeps them grounded when everything else feels chaotic within the business.

And we can't justify sharing our weaknesses if it potentially jeopardizes losing the locker room.

But that's the great irony of this whole situation.

It's never been more important to share weakness & insecurity as a founder.

The state of startups is precarious right now as the rise from zero to 5% interest rates & the slowing of VC investments has discounted private tech startups meaningfully.

This has employees questioning the stability of their employer.

And while there's been a reversion to the mean, more employees are working remote in a hybrid or full-time capacity than ever before.

This makes it harder for leaders to connect deeply with their employees (especially if the company hasn't been full-time remote forever).

It's never been more important to build trust as a leader in order to attract and retain great talent.

Which brings us back to sharing your insecurities.

Brené Brown , who's a world-class researcher, wrote a book called Dare to Lead.

In it she shares four skill sets of daring leadership:

One of these skillsets she calls "Rumbling with Vulnerability."

To be a courageous leader you need to rumble with vulnerability and embrace the suck.

And in her research study she found that there are six myths around why leaders aren't vulnerable.

Myth #1: Vulnerability is weakness.

Myth #2: I don’t do vulnerability.

Myth #3: I can do it alone.

Myth #4: You can engineer the uncertainty and discomfort out of vulnerability.

Myth #5: Trust comes before vulnerability.

Myth #6: Vulnerability is disclosure.

The point is clear.

Vulnerability is synonymous with being a strong leader & sharing insecurities is one way to be authentically vulnerable.

Let me try and demonstrate.

Here are 4 insecurities I felt while building Morning Brew & still feel as a startup founder:

Insecurity #1: I procrastinate too much

Whenever I'm bored or I'm dealing with a difficult mental task, I default to grabbing my phone and scrolling through Twitter or Linkedin.

I think this is partially driven by our biological desire to be complacent and our aversion to putting in sustained mental effort, but I also think social media is a drug and I'm addicted.

When I have a great day of work, I feel like I've done what I've said I was going to do while minimizing my time spent procrastinating.

Insecurity #2: I never knew if I was doing a good job

There's this weird thing as a startup founder where understanding your performance isn't super easy.

You don't have a boss.

If you've bootstrapped you don't have investors or a board to function like your boss.

And a lot of the things you work on as a founder are long-term investments, so you're not getting immediate feedback like most employees.

Which means you rely on imperfect short-term indicators of performance, or if you have a cofounder you rely on their feedback.

In the early days of Morning Brew, my cofounder and I were young, not sophisticated in our communication, and never gave nor solicited this type of feedback out of fear of hurting each other's feelings.

Insecurity #3: I felt like I wasn't strategic enough

Everyone in the professional world is obsessed with the word strategy.

Leaders try to have strategic in their job title and everyone is obsessed with saying they do strategy work.

Now as I reflect on my MO I worry it doesn't line up.

I'm super creative, I'm a storyteller & seller, I share ideas when i'm excited about them not when i've spent days fleshing them out.

And because of that it's always made me feel insecure that my superpowers as an entrepreneur don't line up with being known as someone who is strategic.

Insecurity #4: I worry that i'm not critical/paranoid enough

I'm generally a very tolerant & optimistic person.

And I think this has clear benefits in leadership.

It allows me to be persuasive when I share the vision of a business, it creates a feeling of safety for those that I work with, and it's a sustainable way of being.

But when I think about being a great leader, I think there are two traits that the critical/paranoid mind thrives at:

1) Sweating the details

2) Sniffing out cracks before they become craters

I'm insecure about the fact that my more laissez faire way of leading can lead to irreparable issues within a business.

Now, I want to finish by making something clear.

I don't share my insecurities to be vulnerable for the sake of being vulnerable.

I truly believe that it's wildly important for a leader to be open in this way.

1) It shows a sense of self-awareness. If you don't call out your vulnerabilities, people will wonder if you have the awareness to spot them and work on them.

2) It gives people permission to be open & not fear looking weak or being wrong.

3) It's cathartic. I don't have to carry the weight of these feelings I have all by myself.

Vulnerability is strength & founders must have the courage to embrace it.