Place a bet on yourself

When will you give up on yourself? On your dream of becoming a successful writer, or being known in another creative field?

Will it happen all at once? Will there be a day where you “declare” that you are giving up?

Or will it happen slowly, one missed opportunity at a time? One missed writing session at a time?

Something just astounded me this week. I was reading about the history of the Seattle rock scene in the early 90s, and came upon this passage:

“I thought I might be done with music, at least at that level of playing the game and trying to be on a major label. I was feeling the pressure of being a 26-year-old that hadn’t finished college. There was pressure from the way I grew up to finish something and do it right. There was unfinished business with school, getting my art degree. That summer I went to Western Washington [University] and kind of looked at the campus and the art facilities.”

This was Jeff Ament, the bassist for Pearl Jam just a year before their breakout success. Before Jeff and his bandmates would help radically shift music and the culture.

Can you imagine choosing to miss this? To give up on your creative work the moment before you find success beyond your wildest imagination?

When I read Jeff’s comments above, they resonated with me. Here was someone trying to figure out if he was a quitter or not, and trying to find the right path forward.

Dealing With Doubt

In the past couple weeks, I have been doing three things:

  • Analyzing the biggest challenges that writers and creative professionals who reach out to me have. These are people who have hired me, or shared the insiders account of their goals, their challenges, and their process.
  • Working step by step through the process of finding an audience with my mastermind group. I am in the trenches every day with 20 people, digging through research, ideas, processes, and steps forward.
  • Beginning to write my next book, and starting that process with a deep analysis of what all of my research has told me about the stumbling blocks that hamper creative professionals — the things that keep people from attaining their goals.

As I do all of this analysis, something that jumps out at me is how much doubt people wrestle with. Doubt in their abilities. Doubt in the clarity of their vision. Doubt as to whether they even deserve success.

Finding Your Path

I reviewed some of the conversations I have been having with people in my mastermind group, and wanted to share a three step process for helping you find your own path. The goal is this: place a bet on yourself.

I cannot remove doubt from this process, but I can share advice on what I have seen propel writers and creative professionals forward to success:


Can you imagine the first time that Mick Jagger stepped on stage? Do you think he sheepishly found his groove, and slowly tried out a few dance moves? No, I’ll bet he OWNED IT.

Here he is in 1963:

I want you to consider the confidence that it takes to do what he does on stage here. When I see this, I personally see someone who isn’t the traditionally best looking, doesn’t have a classic singing voice, and isn’t even the best dancer. But he is MICK JAGGER. His confidence, his tenacity, his stamina, his talent, his drive have made him a legend.

Okay, here is the best thing you will see all week, shared with me by author Michael Raymond. Its David Bowie impersonating Mick Jagger:

David describes Mick as “I had never seen anything so rebellious in my life.”

Do you need to be rebellious? Nope! But its worth it to remember that Mick Jagger’s decision to walk out on the stage and do what he does is a choice. You have to ask yourself: are you making the choice to bet on yourself? On your abilities, on your vision, on your own tenacity? Will you own it?


Are you working hard on your creative work, but frustrated because you aren’t finding success? Double down. Get clear on the one or two parts of your vision that is the core of it, clear away everything else, and double down on it.

Do it twice as much, twice as hard, with twice as many ideas, and twice as much vigor.

Is this work? Yes. But it should also be a joy. A joy to find your clarity. To experience it each day. To develop your craft. To know, regardless of external validation, that you doubled down on your creative work, and yourself.

The key to this is not the “doing more work” part, it is in the “clear away everything else” part. Now, I 100% realize that you likely have many responsibilities that you need to live up to: a day job, kids, relationships, health, keeping a home, and the like.

Let me ask you this: do those around you know that you are driven in your creative work? Even if it is just 3 minutes per day, would they describe you as someone who is “obsessed with becoming a novelist”? Not because you gloat, but because they see that you fight to find a few minutes a day to study your craft.

If not, then consider if you have truly doubled down on yourself. Or if your creative vision is at the end of a long list of to-do’s, just after “clean out the garage.”


In one of the assignments I gave to my mastermind group, one of the writers within it sent me her work and asked “Did I overdo it?” I replied, “Um, YES you overdid it, which I think is exactly right!”

In the research and analysis I mentioned above for my own creative work, I have been reading a lot. What I find is that the people we admire and seek to emulate overdo it.

Ed Catmull and his team at Pixar overdoes it.
Bruce Springsteen overdoes it.
Amanda Palmer overdoes it.
Twyla Tharp overdoes it.

I don’t think that “overdoing it” is about buying a bedazzler and writing “I’m Awesome!” on your jean jacket. It is about doubling down on what matters to you, and really committing yourself.

You Define Your Success

At the start of this post, I mentioned Jeff Ament who almost missed out on the success of Pearl Jam. I want to be clear about something: your path forward need not be defined by your work. Not even your creative work.

In thinking about Jeff, I thought of other people who famously “missed the boat” to success. Pete Best came to mind, the original drummer for The Beatles who was asked to leave the group just before their international success.

Did Pete really miss the boat? When reading his Wikipedia page, I came along this line: “He has been married for over 50 years to Kathy Best; they have two daughters, Beba and Bonita, and four grandchildren.” That warmed my heart.

In other words: define success however you like. Regardless of the path you choose, or even the path you unintentionally find yourself on, bet on yourself. Do what you can to quiet the doubt and know: you are worth it.