In our weekly series, we offer a little inspiration to kick-off your week.
Some simple wisdom, elegant and accessible. From one soul to another.
We hope it helps you ease into your Monday.

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How to Fail (like a Boss)

“If you’re not prepared to be wrong, you’ll never come up with anything original.”
~Ken Robinson


Lately I’ve been a big fat stinking failure.
At least that’s the dialogue that runs inside my head on the regular over the last few weeks (in between lyrics to ROYALS by Lorde).

What have I been failing at? A lot.
Like regular Soul to Soul posts. Or writing my own original articles in general. Or taking care of my health. Eating well. Moving my body each day. Getting my taxes together. You know . . . life + business stuff.

I often jump to the conclusion that I’m a failure, because I haven’t done everything and done it perfectly. I wrongly assume that things aren’t getting done because I’m a procrastinator, lazy or even worse . . . I suck at life.

I don’t know about you, but I have a longstanding habit of beating myself up. Over everything. But it’s not overt. I don’t literally flog myself or internally berate myself. It’s more subtle and insidious than that. But it’s still there. This underlying feeling that I’m not doing enough. That I’m not creative enough. That I’m not “on-top-of-it” enough. That I’m not business-like enough.

And you know what all this boils down to? One simple thing.

I am not enough.

A few days ago I was going through a particularly difficult time (probably induced by the copious amounts of sugar I had ingested). Out of nowhere, I stopped everything I was doing (dropped the chocolate) and went into the bathroom to have a good cry. There’s nothing a good cry can’t fix, am I right?

Here’s what I deduced, post-cry: learning how to fail is about the most important thing we will ever learn.

We are NOT going to succeed 100% of the time. That’s a given. We’re going to bomb. And sometimes, we’re going to bomb hard. But guess what? That’s good news. Yes, good news.

According to the wise Seth Godin, failing and failing often is the key to success. She who fails the most, wins? Apparently so!

Here’s a great interview with Seth that talks all about the concept of failing until you succeed. He references entrepreneurship and business, but this principle can be applied to virtually any area of our lives.

It begs the question though, HOW do you fail, not just frequently, but with finesse? Like a Boss!

Here are three lessons learned from my own failures:

  • Trust your 6th sense – using your intuition will help navigate you through failure swiftly and with as few bumps and bruises as possible
  • Remember, it won’t last forever – just like everything in life, this too shall pass
  • Keep moving forward – even when you’re stuck in the muck, overwhelmed by everything and feeling like anything but a Boss, keep yourself moving forward. Take baby steps. Whatever you do, just keep moving forward.

So, what do you think? Are you a proponent of failing frequently on the road to success? Any tips to share about how you’ve navigated failing like a Boss?

To Failure!

Steph Signature with heart




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  1. Ohhhhh, this is how I’ve felt for some time too. Nobody’s perfect, you can only try your best. Keep going, don’t give up and give yourself a breather from time to time! :)
    To failure!

    PS: You are enough!!!