top of page
  • Writer's pictureOlive Persimmon

What to Do When You're In The Middle of Failing


It’s a buzzword on the lips of successful millionaires and personal development gurus alike.

“Fail beautifully,” they’ll tell you from their mansion in Italy.

“You can’t be afraid to fail,” they’ll preach before driving off in their Maserati.

It’s true. Most of them failed. Multiple times. In huge ways. Bankruptcy and homelessness.

When we hear these stories, it’s always after the fact. It’s easy to reflect upon failure in successful hindsight. It’s very, very difficult to talk about failure when you’re smack dab in the middle of it.

I know, because I’m smack dab in the middle of it.

In a lot of ways, I am very successful. Great comedy book, excellent public speaking coach and speaker. Thoughtful friend, loving daughter. However, I also do business development for a training firm. There’s a metric I need to hit each quarter. Quite frankly, I’m nowhere near my metric. In that sense, I’m failing. Beautifully. Except it doesn’t feel beautiful. It feels terrible and embarrassing.

And that’s why no one writes about failure when they’re in the middle of it. We’re afraid that we’ll be judged by this one event. That somehow, our inability to succeed in this one arena may translate to other arenas. We’re afraid that people will judge our character, intelligence, or ambition. We’re afraid that we might never get to the place of successful hindsight.

Yet, we’ve heard from these millionaires that failure is a part of life. So how do we self-correct when we’re on a bumpy course?

1. Assess if you actually want to succeed at this particular thing

Figure out if this is something you enjoy doing. Is it something you want to be successful at or do you just think you SHOULD be successful at it? In the words of Lisa Nichols’, “Sometimes you’re in a lane that’s not your lane.” If this is the case, skip to Step 3.

2.If yes, Look at your current action plan

On a piece of paper, write down two columns. The first column will be what’s working. The second column will be what’s not working. Be specific. Then stop doing the things that aren’t working. Spend more time on the things that are working. If you have nothing listed in the “what’s working” category, look at other people who are successful at whatever you’re trying to accomplish. Start doing those things.

3.Be strategic with your life

Write down your goals for one year from now. Start out by generally assessing what you want in life and then get specific about the thing you’re failing at. When I was younger, my dad taught me a wonderful acronym, SPIDOG. Solve your Problems In the Direction Of your Goals. Use this process when making decisions. Ask yourself, “Am I solving my problems in the direction of my goals?” Create some action steps that will take you in the direction of your goals and hopefully away from failure.

4. Make some moves

Make some moves. Big moves. Or even small moves. But DO SOMETHING. Don’t sit and stagnate. Don’t let your self-esteem get so low that you think you’re incapable of succeeding at anything. Don’t let your failure take a toll on your health, your relationships, and your overall peace of mind. Change your trajectory with action.

5. Sing Some “Journey”

“Don’t stop believing.” Ok, it’s cheesy. Remember that whatever you’re going through is temporary. It doesn’t define you. But in this moment, it feels very serious. You have to have faith that it will pass. Faith in yourself, or God, or whatever it is you believe in. Keep moving forward.

Failing sucks. I know. But I’m also about to make some big moves and honestly, I feel really great about it. Instead of being a passenger to my own failure, I finally feel like I’m back in control, hands at the wheel ready to drive on.

What are you doing to fix some of your current failures?

Peace and Love,




bottom of page