How to turn five dollars into a hundred, in an instant, and for free

It’s funny how much time and energy and frustration I would have saved in my life had I been braver.

Good thing I now know that the quickest route to having an unfair advantage over the seething masses is not in doubling my output or being busier or making more things to share, though these do help.

It is to find that rarely used layer of my soul that can leap into unknowns — even if my heart is bouncing in my rib-cage.

Even a tiny percentage increase in bravery can make a lot of difference in the results I see.

Using bravery over working harder as currency is like going to the exchange and turning five-dollar bills into one hundred dollar bills. They each go further, and you can make the change instantly, and for free.

Well, not entirely free. You pay in extra handfuls of heart-beats.

I remember having a sudden hot flash after realising that I had no illustration client projects happening. No new prospects on the horizon.

Usually — after some intense pacing across my apartment — I would have turned to my big fat database of thousands of email addresses — those who had the power to determine whether I’d be paid that year or not, namely design directors, creative directors and art directors.

I’d had some prior success with these last-minute email blasts to thousands.

That is if you could define success as several hundred unsubscribes, five spam warnings, and two replies that said:

Thank you Alex. You do interesting work. I’ll definitely bear you in mind for future projects.

I thought back to that unnerving feeling that would wash over me after hitting the send to all button. Press it, and an email nuke would explode in a random spot somewhere on the Earth.

All those inboxes snapping angrily shut on my tentative army of electronic envelopes.

No more.

This wasn’t like me, anyway.

The ickiness I felt was like a flashing message that read:

Please increase bravery quotient now (you cowardly git).

Something needed to shift. There must be a better way to do this.

I was missing oomph.

And like a prod in my side, the answer floated into view.

I knew what needed to be done.

I would do like George from Seinfeld in that episode where he did the opposite of everything he usually did — and found that it worked.

Instead of not approaching that girl at the table, he’d go right up to her and tell her that he still lived with his mum.

I would do like George Costanza.

I would do the opposite of what I always did when I needed something.

I would step into uncertainty where the stakes were higher, and I could taste the edge.

With shaking knees and a pounding heart, I would go to the exchange.

I did what I would never do. I did what few other illustrators were doing.

I called a past client.

On the telephone.

With sweat clinging to my phone, after twenty minutes, I said thank you and goodbye.

The conversation went well, actually. I had forgotten to bring business into it until the last minute when I asked whether they knew of anyone looking for an illustrator.

That referral came through within two hours in the form of an inquisitive, creative director at a London agency named Steve.

Bravery had worked, and a penny dropped somewhere in the dark backrooms of my brain.

Doing the opposite of comfortable soon became more of the norm.

Though I still sometimes take the path of least resistance, it has been the bolder moves: those uncomfortable conversations — that have had the most profound impact on so much of what I do.

I thank goodness for the awkward conversations that are still to come.

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”

Tim Ferriss