Overcoming Maybe


It’s such a loaded word, isn’t it? Both promise and defeat. Overcoming “Maybe” and understanding failing sounds crazy, but it is SO powerful that I took an entire afternoon to write this blog post.

“Maybe” holds us back.

“Maybe” is damn difficult to overcome.

“Maybe” threatens to derail us. It is many things to many people. But every “Maybe” has this roadblock in common: our thinking.

“Maybe” is a mindset.

“Maybe” is our own personal mountain waiting to be climbed.

“Maybe” will exist as long as we let it. We will stand there, wondering what might have been…

woman standing in jacket and looking up at mountains thinking about overcoming Maybe and understanding failing

Because it’s safer to wonder than to wander— into action. Into the unknown. Into failing.

But what do we sacrifice when we choose ‘safe’?

Only you can decide that for yourself.

I had to decide for myself. And friend, it was/is NOT easy. In fact, it took me ten years to finally dive into overcoming my “Maybe” and to get past STUCK. And if I’m being honest, there are days I feel like I’m failing. At least, that’s what my ‘monkey mind‘ tells me.

How to overcome “Maybe” and accept failing

You probably won’t like hearing this. It’s not new. And it is much easier to ignore than to do.

The power of Maybe happens this way: Change your thinking. Take action.

Our personal “Maybe” requires our attention. It requires our willingness to face self-doubt, self-awareness, and self-discipline. Even, failure. We have to get ourselves into action while adjusting our mindset.

These are the reasons most people do not overcome their “Maybe.” In fact, they won’t even try to climb the mountain.






Embarrassing… Humiliating… Stressful… Scary… Challenging… Uncertain… Fill in your blank ______________.

Why failing is key to personal success

Ask anyone who’s found success or is working toward it (however they define success). Failing at something is a GOOD thing. Yes, it stings. Hurts. Is hard to accept. But failing at something provides perspective. Humility. Information that comes from trying. Failing at one thing means you can redirect and try another angle. I absolutely love Sara Blakely’s take on failing! The founder of Spanx learned at a young age that the secret to success was being willing to fail.

As I used to tell my high school juniors and seniors in the classroom when they felt they had failed: Feel the feels for five minutes. Be angry. Embarrassed. Sad. Defeated. Then… ask yourself what you learned from it and move forward! (But do NOT skip the self-assessment part. It is key.)

The process matters

Overcoming Maybe is part of a process that requires work. We can’t truly enjoy the victory if we don’t slosh through the mud. I can hear you, “Oh, but I can!” Actually, science says otherwise. Humans are wired for anticipation more than reward. Strange but true. We talked about this in our Atomic Habits book group. We were both surprised and fascinated!

Here’s what I’ve learned about failing. If you fail…

  1. You showed up and tried.
  2. You have new information (and are hopefully learning from it).
  3. You are willing to stand out from the rest of the pack alongside these well-known folks.
  4. And most of all — You are brave!!!!!!!!
infographic about failure by anna vital in a discussion about Overcoming Maybe and Understanding Failing

This is it. Pep talk done. Are you ready to tackle a Maybe? Are you scared? No problem. (Me, too.) Every damn day. Do you have confidence in yourself? I do for you. Let’s start there. I’m cheering you on from here, even if we’ve never met, because I KNOW overcoming “Maybe” and understanding failing is possible for you. 🙂

signature Robin

p.s. Wondering why I chose “failing” instead of “failure” in this post? If you are, awesome! You’re dialed in. Here’s why— “failure” implies finality and completion. Game over. Contrarily, “failing” implies action. If you are failing, you are taking action. Game on!