The Humble – Confidence Dichotomy of Successful Entrepeneurs

When reading this post by Brad Feld, I was reminded of the challenge that is being an entrepreneur and leading a company. In Brad’s post he talks about a couple of strong, capable entrepreneurs that were starting to have self doubt. Brad suggests a way out of this self doubt using inquiry. Go read his post to learn about that.

What hit me about his description of self doubting entrepreneurs was how much of a challenge it is to be an entrepreneur. As the founder and leader, you’re constantly walking the tight rope of humility and confidence. You have to be humble enough to not compare yourself to others (and other companies), while keeping your confidence for the rest of the team.

Both of those characteristics are hard to manage.

I think by our very nature we want to start comparing ourselves to other people. If it’s not in our nature, then it’s in our culture. Either way, the ability to not compare yourself to others is a challenge. When you talk to other entrepreneurs you rarely get the whole story. They only tell you the exciting and wonderful parts of their business. They seem to avoid telling you about their fears, anxieties, pressures, stress, and even failures.

Since all you’re hearing is the great things about other companies, it’s not even fair to compare your business to another. Even if you do hear the challenges of another company, there’s still little value in finding your self worth in your company being better than another company. Guess what? It doesn’t really matter.

Related to the above challenge is the entrepreneurial challenge of remaining confident for the rest of your team. There’s a reason that a coach is so great for an entrepreneur. It gives them someone to share their deepest fears that they’ve kept bottled up from the company because they want to maintain the culture.

I’m not talking about lying or misleading people in your company. You should always speak frankly, honestly and openly with the people who work with them. However, the best CEO’s know when is the time to keep your fears to yourself and when is the time to share those fears with the company. Often some things are better kept unsaid.

Thus the dual life of an entrepreneur. I’d love to hear your thoughts on this challenge. How do you deal with it? What have you seen?

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4 Responses to “The Humble – Confidence Dichotomy of Successful Entrepeneurs”

  1. Julia Says:

    In some ways, being an entrepreneur is not that different than being a leader in a company or a business division. As soon as you have people reporting to you, you really need to choose your words carefully. And as you climb the ladder, this is magnified.

    Certainly, we all have bad days – but it’s tough to articulate that to anyone but a peer. No subordinate wants to hear that their boss (leader/owner) doesn’t feel like working today!

    It can be troubling to an employee to hear “I don’t know where to take the business next.” On the flip side, it’s good to solicit input from team members. All in striking a balance.

    When the issues are business-related, it’s important to have a sounding board or outside third-party. Might explore the peer groups for entrepreneurs and leaders out there. One I’m aware of is EO – another is Young Presidents. I also like the NYT blog “You’re the Boss.”

  2. John Says:

    Well said Julia. There is certainly a lot of similarities between startups and larger companies. That balance is hard. Plus, the need for peer groups is definitely the key. Having someone else who is going through the same issues is very powerful.

  3. Francesca Gershwin Says:

    Wow, this is a great post.

  4. John Says:

    Thanks Francesca. I try to put a little bit of my heart in every post. Hopefully others find it useful.

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