What I needed to lose to get what I really wanted

Dessa Brennan
Jul 24, 2017 · 5 min read

I’m learning a valuable lesson.

To live a life on my own terms. To not have a boss. To live where I want. To work with people of my choosing. I have had to forget about the need to feel confident. I’ve had to separate from my ego. Instead, what I’ve needed is courage.

Courage is what I relied on to leave my full-time job in October of 2015 as a Human Experience Strategist at a global media agency.

Confidence is backward looking.

I left that job feeling confident that I would not lose the skills I had honed after ten years of practice.

Courage is forward-looking.

However, it was good old-fashioned courage that I needed when facing whatever unknown obstacles would come my way.

I left my full-time job without work lined up. I did not know exactly what I would be doing, with who, or where. I did not know if I’d be able to make money.

This scared me, but courage kept me moving forward in the game.

Confidence that I wouldn’t lose what I’d already gained in work experience was my safety net.


Yet, I believe confidence is over-rated.

It’s a measure of proficiency. It can be ego-led.

My confidence has come from positive feedback. It’s also the result of lots and lots of practice. Being confident feels good to my ego. My ego wants to always be taken care of. It’s selfish and demanding!

Comfort is to Confidence what Discomfort is to Courage.

I’ll never forget the sheer panic I had after I first got promoted to an account executive while working at Leo Burnett, a global advertising agency.

All of a sudden I was expected to speak in client meetings. No big deal, right? Wrong. You see, at big agencies like this, junior staff is often prohibited from attending, much less speak at a client meeting. (Silly, right?)

This type of set up squashed my confidence. I left college ready to take on the world, and entered a very bureaucratic work culture. I went from leading projects in college classroom settings, to taking notes for other people in a junior account management role. I lost my voice because I wasn’t expected to use it.

Until one day, I was promoted. Then suddenly, voila! I was in. I could attend meetings. I could contribute beyond written summary notes. There was just one problem, by this time in my career I had been silenced for so long that I didn’t have any practice speaking in these meetings that were built up to be big and scary.

I thought I needed confidence to get past my fear. That I could posture and pretend I wasn’t nervous. Bullshit. What I needed was courage. I needed to let go of my ego. My ego felt the need to be perfect, to prove to everyone that I was there for a reason.

If I had let go of my ego’s need to be seen, then I could have had more fun.

Looking back, I wish I could have told myself…

“Hey — look, you get to do something you’ve been wanting to do for a while now. Have the courage to just go for it. Know you’ll mess up, and sound stupid.

But don’t worry. You don’t need to be the smartest person in the room. You don’t have to prove yourself.

You can just be you, and you’re loved for that. This job and this meeting don’t make you more or less worthy of love. It’s just a meeting. So have fun with it, okay?”

Gosh, I wish I had that level of self love back in that moment. I wish I had that self love in any new moment. It’s much easier to write it, than to act it. But I’m getting there.

This is a nice time time to segue into courage.

As you can see where I’m going. I think it’s way different than confidence. Yet in spending time around entrepreneurs, I often hear the two used interchangeably.

There’s the common mantra to “fake it ‘till you make it” with the insinuation that you just need confidence to get you through it.

But I don’t think that’s true. If you are doing anything new it’s illogical to expect to do so with confidence.

Courage is what you muster up to do things, irrespective of knowing the outcome. Courage isn’t fed by the ego. It comes from a place of love, and knowing you’re worthy regardless of the outcome.


There are three ways I think about everyday scenarios that feel uncomfortable:

  1. I can be confident, but not act courageously. (Lame.)
  2. I can be courageous, but recognize that I don’t yet have confidence. (Most likely.)
  3. I can be confident and courageous. (Ideal, but rare.)

To try anything new, I must consciously let go of my ego’s need to feel confident.

Courage is what’s needed to live my most interesting life. For me interesting comes from the unknown. I need to constantly be discovering the new. As long as I hang onto my need to be confident, there’s no way in hell I can be happy. I’ve got to prioritize courage, and let confidence come in due time.

CONCLUSION:

Confidence is not the guidepost for creative living. If anything, my ego’s need for it can be what holds me back.

If you need to feel confident about everything you do, then stick to what you know. Stay in your lane. Do not seek out the new. Be okay with the status quo.

But, my guess is that’s not you…

IF YOU WANT TO LIVE YOUR BEST LIFE:

Let’s set-up a time to talk. I’d like to understand what’s on your mind as it relates to your career and finding meaningful work.

I’m finding the principles I’ve used in 10+ years of strategy for brands apply to the most important brand and campaign of all — who I am and how I spend my time. This includes my career, and other aspects of life. I want to share how these frameworks can apply to your life too.

A final favor: If any of this post resonated with you, go ahead and hit the💚 so that I know to keep writing more like this. Thank you so much!

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment.

Dessa Brennan

Written by

New mom. Strategist. Writer. Partnering w/ wellness brands through honest writing that compels people to act: www.spinachstrategy.com

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment.

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