17 Ideas For Being Bold And Reducing Regret

Because risk today reduces regret tomorrow.

I’ve been an entrepreneur for over 30 years.

I’ve had my ups. I’ve had my downs.

I’ve ridden the rollercoaster — and sometimes thrown up.

I’m made more than my fair share of mistakes.

But I have less than my fair share of regrets.

There’s a reason why. I had this remarkable realization many years ago.

The realization that what few regrets I do have are not about the mistakes I had made, but about the mistakes I failed to make because I wasn’t bold enough.

So, my two word advice to reduce your regrets when you look back on your journey years from now:

Be bold. Risk today reduces regret tomorrow.

1. Be bold.  Go after that big, powerful incumbent that doesn't delight its customers enough.

2. Be bold.  Hire that awesome, amazing person -- even though they don't fit any of the roles you're currently looking for.

3. Be bold.  Make that sacrifice that will negatively impact your numbers in the short-term but that you know in your heart is the right thing to do for the long-term.

4. Be bold.  Make that really hard decision that even the smartest people you know can't seem to agree on.

5. Be bold.  Say no to that accomplished, super-successful person that your team interviewed, loved and convinced to join -- but doesn't fit or further your culture.

6. Be bold.  Kill that silly company policy that nobody can recall the rationale for, but you suspect was because someone (maybe you) had a friend who knew a guy that had read about a startup that didn't have that policy and that company failed.

7. Be bold.  Launch that super-secret project you've been working on even though it's more likely to fail than succeed.

8. Be bold.  Admit that you were wrong and have changed your mind on the decision you so passionately advocated for a few months ago.

  1. Be bold. Allow yourself to try the thing that’s been tugging on your brain for years. It may seem like you’re betting the company or your credibility, but you rarely are. Even if you fail, you’ll learn something — and free your mind for future follies.

  2.  Be bold. If you have a brilliant idea that you know is not a good fit for you — and likely never will be, share it with the world. Perhaps someone else will pick it up.

  3.  Be bold. Give yourself permission to part ways with that awesome person you hired who is no longer delivering awesome results. Chances are, they’ll go back to being awesome — somewhere else.

  4. Be bold. Have the courage to the fight the complexity that insidiously tries to creep into every organization. Fight for simplicity, and be prepared to emerge bruised, tattered and sometimes defeated. Complexity is a beast but the fight is noble.

  5. Be bold. Drop the dogma that is now masquerading as culture in your company. It’s OK to honor your history but don’t let it hold you back.

  6. Be bold. Concede that sometimes you followed the crowd instead of following your heart. It happens to the best of us, often in the worst of times.

  7. Be bold. Have wildly ambitious aspirations. These wild aspirations have a secret power that few talk about: They attract wildly amazing people.

  8. Be bold. Push those around you to be bolder — and support them when they take their own bold leaps.

    And finally:

  9. Be bold.  Confess to yourself, and others who support you, that there was a time you wish you had made the bolder bet and chosen the more challenging path. It’s OK to have regrets. They can embolden you in the future.

Being bold creates dots. These dots may not quite connect right now — and some of them may never quite connect. But when they do…BOOM!



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