The image of “success” paints a deceitful picture of ease.

It quietly misleads onlookers into assuming that this person has got things easy. It falsely conveys that someone has “figured it all out.”

That’s because we’re on the outside looking in and seeing only one fraction of a snapshot of what’s resulted from thousands of hours of struggle and hundreds of missteps, failures and fuck ups.

From the outsider’s perspective, all we see is someone who’s “crushing it.” A writer who seems to never leave a sentence astray; an entrepreneur who preaches like a priestess, so infallible is her every sermon.

We see “success” from the outside and think, this person just doesn’t miss a beat.

He’s got this scripted. She’s got it all thought out.

There’s no improvisation–it’s all meticulous, it’s all methodical. He’s winning. She’s succeeding.

When you’re succeeding, we reckon, you don’t screw up, fail or flop–you know ahead of time what’s gonna work and what’s not. What’s going to sell and what won’t. What will go viral, be swept up and sell out, be clamored for and utterly loved. You’ve “got it figured out.”

And because you know what’s going to succeed and what’s going to fail, you don’t have so much to worry about, or stress over, or endlessly question or doubt or dread.

The image of success is sneakily dangerous–because it creates a false illusion of ease that we assume we can achieve through fail-proof methods and infallibility. The image of success hides what is actually required to make strides, defy uncertainty and to tread an unknown path: grit, heart, and letting go.

But when we look at the image of “success,” we see only the outcomes.

We try to emulate the result, because we want those results.

We want the acclaim. We want the capital to hire a team to do the heavy-lifting for us. We want our readers to hang on our every word. We want our books to be pieces of art within themselves: beautiful, memorable, lasting representations of everything we have so long believed and stood for.

But we lack the brash and brazen to even write that first book at all.

So we put it off–we delay the tough decisions and difficult choices until we’re “ready” or have “figured it out.”

Worse than being afraid of failing, we’re afraid that we’re not ready–and that some magical place exists where our worries and fears and hesitations will disappear because we will have “figured it out” enough to choose what we want, pursue the lives we desire and claim what is rightfully ours.

We’re so afraid that we’re unready that we stop ourselves from even trying.

No matter who you are or what you do, fear and doubt are constants in this life. Life is nothing but uncertain. And no amount of mastery, expertise, skill, popularity, follower counts or talent changes that fact of life: everything is perennially unknown.

I believe that why we don’t pursue our dreams fully or quit our terrible jobs, leave unhealthy relationships or do anything that is otherwise “risky” is because we maintain a false belief that we can reach a certain emotional place or position of “safety” from which uncertainty will feel less daunting: when fear won’t be so fearful, when leaping won’t feel like falling without a net to catch you.

Something like a place of “success.” Where we think we’ll “know what we’re doing” or “have it all figured out.”

We want to believe that we can reach some place–whether in our lives, or in a loving relationship with a partner, or in business, or as an artist–where the fear and unknown go away. We want to get somewhere where uncertainty disappears because feeling uncertain sucks.

And then we look around to see people who seem to have it “figured out” and assume that they don’t go through these feelings. And that, in turn, reflects back to us and instills this quiet shame and deep worry. We see ourselves in that reflection and think that we’re lacking. Incapable. “Less than.” And because we don’t have it all “figured out” like that successful person, we stop ourselves from trying before we’re ready. We spend weeks preparing, months pondering, even years trying to “figure things out ahead of time” when in reality we’re too flat out terrified to figure anything out at all.

…because when we figure it out, we’re responsible for what comes next.

There’s no going back.

There’s no way to unsee what you see.

The image of success makes us afraid to fail. Afraid to fall. Afraid to look flawed, afraid to guess as we go, afraid to figure it out on the fly–afraid to, you know, be human.

And that’s why we’re here today.

After five years of ups and downs and reaches and struggles, I have a business that’s finally working for me. I’m starting to build a team to assist me with different duties like running my writers’ group, The Literati Writers. And, just having relaunched this blog with its beautiful redesign feels like an exclamation point on the end of a couple of tough, well-earned years of growth and struggle.

I feel proud. I feel like I’m succeeding.

But, after those five years of ups and downs and reaches and struggles, I feel like there’s never been a more important time for me to look back on my biggest business missteps and creative failures to reflect on just how often in this journey I’ve been so woefully unprepared, unready and grasping at straws.

And, I want to walk you through them as living examples of failures that still serve me in very real and meaningful ways today.

The only reason that I have any “success” to speak of is because of this long list of failures, quits and busts–projects that didn’t pan out as I had hoped because I had nowhere else to go but to try before I was ready.

Turns out that, even years later, some of my most lackluster projects and mediocre efforts still manifest themselves in my successes today.

They’re still helping me to succeed.

I hope that these reflections will help you takeaway some key beliefs that I would love for you to consider embracing and applying in your life, art or business:

  • Don’t be afraid to start before your ready. The most honest strides you make towards your goals are by doing, not waiting.
  • Don’t be afraid to destroy what’s not working–and, just as much, don’t hold back on destroying it just because it is working.
  • Don’t think you’re ever going to “figure it all out.” You never will–that’s a good thing. But, more on that later.

1) The Renegade Brand: A first attempt at blogging and branding  (2009-2011)


What it was: My first personal brand, and the very first iteration of the website you now read.

It’s May 2009, about two weeks before I quit my job and abandon my career in public service to “make it on my own” as a writer. I buy this domain,, and set out to “figure out a brand” for myself.

Why? Because that’s what you do. It’s what you’re told. All the advice I had been consuming across the blogosphere was telling me that I needed to be distinct. Different. Unique. I needed to be memorable. I needed to become the Coca Cola of writers–the Nike Swoosh of personal development voices who offered some unique, different, unconventional “edge” and spirit that would motivate people and show them a side of me that is “off the beaten path.”

And branding was that Holy Grail of showcasing yourself: building something memorable and distinguishing yourself as unique enough to be remembered by visitors and readers online.

What it became: The “Renegade” brand was a representation of me before I really knew myself.

“Renegade” was a title that I self-assigned with hopes that visitors would associate with this feeling of being a “chosen outcast” from a status quo that they, like me, did not believe was the ideal end-goal or the only thing that was possible. I used the title of “renegade” to describe my ideal readers, customers and clients–that was my first client profile or reader avatar, in that way.

We were the ones who were different. We were not satisfied with what was conventional. We were dreamers, believers, and fighters for ourselves and one another. It was as if to “believe” in yourself in today’s world, you’d have to be a renegade. A badass in your own way.

(Turns out, unbeknownst to me, that author Jonathan Fields also was using this moniker to great success around the same time).

Why I call it a failure: My Renegade brand was ultimately more effective for segregating readers from me than it was something that helped them relate to the guy behind the computer.

Instead of pulling visitors to my website with a personal introduction that made you feel like you were meeting a friend or peer, the Renegade brand seemed to tell visitors, “I’m different than you.” But then again, more than the “renegade” slogan, what segregated readers more was the fact that I failed to truly understand how important it was for my brand to be me, front and center.

I told some personal stories and my dot com was my own name, but as you can see above, I didn’t even show my face in any pictures for the longest time. I rationalized this decision with, “It should be all about the words, the stories and the message, and not about me.” In reality, it was a way of skirting responsibility, accountability and ownership of my mission. And, it meant no one could meet the human being behind the computer.

What I did right: Everything about my first online brand was wrong for the message, goals and values that wanted to convey–I just didn’t understand them yet.

And my first attempts at “branding” reflect a period when I was dying to believe in myself. I had to start somewhere because I needed to start something in order to keep myself going.

At the time, I was still working to pull myself out of depression. I still thought I was out of my skull for quitting my job in the middle of a recession to be a writer–especially because I had no life experiences to tap, or real achievements to count on, or any amount of know-how to speak of. But, you’ll notice, I’m still here.

The victory was that I did it at all. I started something. I didn’t try to figure it all out ahead of time. I started to learn by doing. I threw something at the wall to see what stuck.

And as more time passed, I learned and iterated, grew and evolved. I started to get better at unraveling the layers of who I was–because I knew I needed to reveal them for anyone on the other side of the computer to give a damn.

How it’s still helping me succeed: By writing so much for my blog in the early days, I began to understand what the heart of my message was.

Putting myself out there pulled me out of depression. I had a new mission and purpose beyond the suffering in my own head.

And, the more that I wrote, I started to feel themes and notice points of resonance. In the act of doing, I explored my way into a sharper and more focused understanding of who I was, and what my goals were, and what my personal appeal was to other people. I gave myself the chance to learn why people were reading what I wrote at all, even if the brand didn’t help them meet the real human being on the other side.

How you can avoid failing like I did: Every few months, I’ll connect with another young person who’s spending an incredible amount of time, effort and energy into creating a brand just like I did. They think this is the way they have to go–it’s what advice is available to them, and they look at other sites and blogs and online personalities to try to create an image for themselves that other people might jive with. They create logos for themselves and catchy slogans. I see myself in them.

You can avoid spending two full years figuring out what I ultimately figured out with this single bit of advice:

It’s not about the brand, the image, the logo or the slogan; just become more you.

I spent too much time trying to figure myself out through the lens of how to describe it, or what titles to give it–what monikers, slogans, tag lines, titles, bylines, description blurbs and countless other descriptions.

Those “branding” elements are surface-level strategies that hide the depth you need to be tapping. Bypass them by instead striving to understand yourself more and more.

Share that. Articulate your story. Show your face. Look into the camera and share a picture of yourself (instead of looking away, sheepishly), so that the reader can actually look a human being in the eyes (even if it’s through the computer screen).

If your goals are anything like mine, your brand shouldn’t be about something other than who you are, what your story is and why you do what you do. Your brand should articulate itself through your actions.

If you want to figure out your brand, spend more time and care and consideration understanding more about you: your core values that shape and define how you strive to live your life every day, the life-shifting moments that set you on this path today, and what, exactly, in concrete and tangible terms, you’re doing to help that person who’s looking your way.

2) RenegadeTV (2010)


What it was: A video-blogging project.

What it became: RenegadeTV was a result of my realizing that hiding my face and personality from my first blog iteration was holding me back from truly connecting with readers through the computer as I wanted to. So I sat down with the camera for a couple hours a day for a few weeks and developed a short series to discuss the things I liked to talk about.

I hoped for RenegadeTV to become a sort of go-to videoblog series for conversation around personal development with an authentic edge and flavor. In the end, RenegadeTV became a 15-episode series that covered a handful of topics that coincided with themes and ideas that I explored in writing on my blog.

Why I call it a failure: It’s tough to call an experimental foray into something like video-blogging a failure–it simply wasn’t all that special. And based on the screenshot that you can see above, I left a lot to be desired in the quality of what I put out there with this project. Everything was very haphazard, improvised and unscripted.

That’s all well and good, but if you’re cultivating something and want it to be truly meaningful to people, you really do need to invest more into your efforts than just “hoping for the best.”

What I did right: RenegadeTV helped me get comfortable on camera. It reinforced my need to connect with people “face to face,” even through the computer. And, I got to show off my sweet spray-paint Spiderman t-shirt. Win.

How it’s still helping me succeed: Every instance of putting your face and voice to your words is a victory in my book. Every act of self-expression is a win.

I know that I got to speak to people (for the very first time) in my own voice and that what I said on RenegadeTV was truly me. And in spite of every episode feeling like a tortuous “I wish I wasn’t doing this” experiment, I emerged better for it, and more confident with what I wanted to share.

In more tangible terms, these days I interview best-selling authors, artists and entrepreneurs as part of a popular feature that I host called “Live Author Interviews” on behalf of The Literati Writers. Between hosting these interviews and being hosted for a hundred or more of interviews since, I never would feel as comfortable as I do on camera and being recorded if I didn’t spend so many hours cutting my teeth with RenegadeTV.

How to avoid failing like I did: Try to concentrate your creative energy, even the experiments, with more of an intentional focus and effort that yields a higher quality product. For a long time, I did the opposite and spread my creative energy far too thin, yielding many little side-projects that were consistently lackluster.

If I had my choice about it, I’d go back and change that.

3) Renegade Apparel (2011)


What it was: A t-shirt business to promote my website and writing.

What it became: Come 2011, I was living in Boston and with a couple of years of blogging under my belt and barely enough money to get by, I starting to experiment more with varying the mediums that delivered my message and possibly bring new people into my mission.

One of the ideas I had was Renegade Apparel: still an iteration of the ‘Renegade’ brand.

Renegade Apparel involved me designing and printing a series of t-shirts with different slogans or phrases that I’d take from popular pieces my blog, before turning around to sell those to readers who might want to wear those words front and center.

Why I call it a failure: It was an experimental project, but when I look back I admit that I was really trying to bullshit my way into making some easy money.

The first print of Renegade Apparel was also its last: I had a stock of about 50 black-and-grey t-shirts, of which I think I sold 5.

The modest loss of about $300 or so taught me a few valuable things:

  • Why the hell do I care about t-shirts?
  • Maybe I’m thinking way too highly of my t-shirt design abilities
  • If I ever want to do something like this again, I need to let potential customers into the equation so I can figure out what they want and how they want it.

What I did right: Chalking the business side to a loss, I figured I could still try to do something positive with the stock that I had left over.

So I used the t-shirts as gifts.

I mailed a few dozen of them to online connections and digital friends along with a hand-written letter. My intention wasn’t about getting these friends to even wear them or promote me so much as it was about the gesture, the gift, and creating some bond of “reality” to our otherwise digital friendships.

And, those little and seemingly insignificant gestures ultimately helped to gel some real, genuine and meaningful friendships to fellow bloggers and creative entrepreneurs that I still have and value these years later.

How it’s still helping me succeed: I’m not wasting my time peddling products–I’m a writer, after all. A foray into products like apparel or t-shirts was simply never for me to do. It was never my zone of genius. It was never anything that was rewarding for me.

How to avoid failing like I did: Keep your creative experiments tight to your true passion. This way, even missteps or failures still help you learn about yourself and your craft.

4) Renegade Guides (2011)

What it was: A series of PDF e-guides.

What it became: By early 2011, Renegade brand was in its waning days, and I was planning to start a side-hustle of digital guides that I called Renegade Guides.

The idea was a simple play-off of a trend made popular by Chris Guillebeau and his Unconventional Guides: nice PDF ebooks on a variety of topics. I had 8 ideas, and started and stopped each one countless times.

Why I call it a failure: I never launched a single guide.

Looking back, I wasn’t focusing my time, attention and creative energy into a need–I was trying to create 8 guides before I created a single one.

What I did right: Instead of bothering with a series of e-guides, I started to think about writing my first book–the book I had been thinking about for years, Lead Without Followers.

How it’s still helping me today: My failure with Renegade Guides taught me to start from where I am, wherever that is, and focus my intentions and energy into as small a space as possible–with one. Plotting too big and too far in the future doesn’t help you accomplish the real achievement: getting one thing done, right now.

How you can avoid failing like I did: You always need to start where you are, so I wouldn’t ever tell someone what project ought to be their first. But I will tell you this: today, e-guides and PDFs are purely forgettable. A book–even a bad one–is still a book. And a book distinguishes you on a variety of levels that people remember–and that you never turn back from.

5) Lead Without Followers (September 2011)


What it was: My first book.

What it became: Lead Without Followers was a book I had been thinking about–and putting off–since the autumn of 2008.

With a load of encouragement from friends and peers from 2010 to 2011, I finally committed myself to writing the book in that summer. I hoped that the book would put me on the map as a writer and author, and would function as my “breaking out” in ways that would help me attract new opportunities like speaking gigs and more.

Why I call it a failure: I never loved what my book became, but I knew that I could never love what the product was because I lacked any real ability to make it as spectacular as I wanted to. I had no choice but to start from where I was.

My writing was still developing. My writing process lacked the values that I didn’t yet understand I needed to incorporate into my creative process. I failed to narrow my target demographic to high school and college aged readers who would resonate with the story and see themselves in me, instead promoting the book far too widely and broadly.

But when push came to shove, I knew in my heart that I had to bite down on my ego and see what good in this book that I could to accomplish the tall task of publishing it.

I wrote Lead Without Followers before I was “ready.” I wrote it before it was “ready.”

I had nowhere else to begin. Nowhere else to start but too soon. No other method than to just buckle down and do it. After two years of calling myself a writer and having never done anything significant other than blog posts and e-books, by June 2011 it was time to really do something to make a statement–to others, sure, but I needed to prove something to myself as well. As a writer, writing a book was the answer. I spent 84 days writing my first book, which came out to be about 60,000 words. I hustled to publish the book just one month later.

After its first six months, Lead Without Followers received plenty of praise and plenty of criticism. I estimated about 2,000 copies sold in that time. It led to speaking opportunities at two universities. The victory of this first book publication was that it was my official “stepping out” as a writer–and as an artist. But the downside to this great, audacious act of artistry (that I still remain so proud of) is that my expectations for it were so, so wrong.

What I did right: Wrote the damn thing. Pulled off a major marketing blitz widely. And, truly changed as an artist.

How it’s still helping me today: I became an artist, and my whole outlook changed. My second book, God Whispers on the Wind, is a product of this first book. I explain the story of how that book resulted from my first over here.

How you can avoid failing like I did: Hip hop artist Macklemore says in one of his songs, “Expectations are resentments waiting to happen.” Damn, is that true. My own expectations for Lead Without Followers were unrealistically high.

To avoid the pitfall of overly high expectations, remember that you are creating to inspire a result for your reader–you’re not creating to inspire a result for yourself.

Take some pressure off of yourself. You’re not here to “perform.” Your art is meant to help people see more of themselves. Accomplish this, and your book will exceed your own expectations.

6) The ‘Unleader’ Brand Iteration (2012)


What it was: An evolution of brand and platform–and one last, final push to make my “leadership” focus work, or be blown up.

What it became: After my “Renegade” branding was killed off in late 2010 and a much cleaner and more “me” version of my platform emerged throughout 2011 with the debut of my first book, Lead Without Followers, by 2012 I was knocking on the door of my move to New York City. I spend a good six months after my book’s debut to travel and process what was happening and what I needed to see happen next.

The “Unleader” brand evolution was what resulted: a deeper iteration of my exploration of personal leadership and alternative leadership. One thing I that heard from readers of my book was that they wanted to know what it meant to “live without followers” in business, artistry and life. Throughout 2012, my creative projects maintained this focus:

  • The Unleader Handbook: A book based on 100 questions on personal leadership submitted by readers of Lead Without Followers
  • The Unleader Academy: A course for helping young leaders embrace personal leadership in their businesses, artistry and everyday lives.
  • Unleader Alchemy: A higher priced, self-guided product to help young leaders shape their messages and branding efforts into “leadership gold”

Why I call it a failure: Ultimately, I never completed or launched any of these products. I was drained. I was unenthused. I was pressing too hard to make them happen, and there was no deep need or desire for them. It was a failure that needed to happen, along with the entire leadership-focus of my brand and writing and work, which, months after Lead Without Followers was published, I was losing enthusiasm for.

What I did right: I blew it all up. The leadership stuff, the projects, the products.

It’s hard to blow up something that’s been your creative focus and passion for so many years, but sometimes destruction is the greatest means of rebirth and renewal.

The alternative leadership focus of my work was no longer serving my wants and needs. I felt like my efforts were going unheard. I myself was losing passion for my work, and it seemed that readers and prospective clients were, too. It was time to destroy what was no longer working. I blew it up.

How it’s still helping me succeed today: The Literati Writers, my online writers’ group and main business gig these days, is a direct result of my recognizing the need to go back to my roots as a writer and creative.

I founded the group in the August of 2012 and we’ve been called home to more than 80 writers since.

In 2014, my goals are to take the group to 150 members, publish two collaborative books on behalf of the community and take our mission to the next level.

How you can avoid failing like I did: Understand that you will eventually need to reinvent yourself–because you will always be changing and evolving. Embrace it.

7) Writing with Aloha (March 2013)


What it was: A two-day writing intensive consisting of four interactive workshops, broadcast live from Hawaii.

Around this time last year, I was planning on spending 5 weeks in Hawaii with my buddy Jacob. We were going to Hawaii because we could work from there. Beyond just hanging out in Hawaii, I planned to spend a lot of time in my ideal creative zone (with a lush backdrop) to see if creativity flowed when the setting and circumstances were nothing but blissful and ideal

And I thought, how great would it be to host a cool event with Hawaii as the backdrop, and center the focus on the digital event around a Hawaiian theme? Better than that, how great would it be for me if I could finance my entire trip with this single two-day gig?!

What it became: Although my intentions were good for creating this event and offering some really specific and important workshops to help writers (based upon the previous 7 months of my work with The Literati Writers), my initial focus for the offering was in the wrong place, which led to a slippery slope and caused the event to fail.

With the ultimate goal to generate a certain amount of income for the event, I based most of the details of the offering on expectations (around how many people could I get to join to make that amount?) and ideals (what’s a healthy price that someone would pay for this vital content?).

Subtle as it may be, with these kinds of details the focus for the offering’s creator, in many ways the important details for the event are misshapen and shifted away from where the focus should be: concrete benefits, tangible takeaways, serving others / alleviating pain-points / helping the customer

Why I call it a failure: I sold zero tickets. The event was entirely overpriced at $308. I priced it according to the quality of the content, an abundance of one-on-one time, and my hope to keep the event very small and intimate (around 8-10 students).

What I did right: The event didn’t cost me anything, and when push came to shove, I realized that my heart wasn’t into this event.

That lack of excitement meant I had no enthusiasm for marketing, promoting or selling the event–and it must have showed in prospective customers.

I chose to scrap the event and pull the available tickets a couple weeks before it was scheduled to happen, and turned the lesson into a positive example for members of The Literati Writers of when you need to gut-check and scrap a project when it’s just not working (whether for you or for your ideal customers).

How it’s still helping: Every time you price and try to sell something, you learn.

But Writing With Aloha still lives on in spirit with my forthcoming writing and yoga retreat, which is happening this January 17 to 19, 2014 here in my beautiful home state of Rhode Island.

Weekend in the Woods, though not taking place on a Hawaiian beach, embodies everything in a weekend event that I could have wanted with Writing With Aloha, but never could have accomplished:

  • An intimate in-person experience where people are together to converse, discuss, explore and make friends
  • Three writing and creativity workshops, a guided morning meditation, a silent writing session, plus two energizing yoga sessions led by my favorite yoga teachers in the world
  • The tools, strategies and mindset that all participants will carry away with them from our weekend together and into 2014

I present you this long list of failures, first-tries and flops (that I’d rather forget than resuscitate) for this reason:

We spend too much of our lives looking “up” at people who appear to have “figured it out.”

The best-selling authors. The stadium-filling speakers. The experts. The gurus. The masters. The celebrities and television personalities, the rockstars and athletes.

I’m certainly not any one of those. But, you and I, some part of us wants to be them.

We wish we could have what they have–the wealth, fame and acclaim–because, we reckon, those things would make life less uncertain, and love easier, and business less risky.

We look up and aspire to reach the levels of celebs and pros, gurus and business icons because we imagine that “getting there” means we won’t keep feeling inadequate. That we won’t feel like frauds for trying before we’re “qualified enough.” That we won’t have to risk failing fantastically–letting ourselves down, or imploding in public and feeling the shame and hurt of failure.

What I’ve learned from failing more than I ever thought possible is that it’s not any amount of money, fame or acclaim that helps you “figure things out.” The failures do. Doing does.

You accrue bottomless confidence by running the barrel dry more times than you thought possible and discovering, every time you’re tapped out, that there’s always more self-belief to be siphoned to the top.

The greatest strides that we make in our lives–all of our hero stories, the triumphant victories, and the badges we wear–are earned in the blood, sweat and tears of overcoming.

I’m here because of how much I’ve failed. And how often I’ve quit. What projects I’ve blown up, books I’ve shred, ideas I’ve ripped down and thrown out to start over again. I’m here because of setting expectations so unrealistically high for myself that I had nowhere else to fall but a place of dejected disappointment.

Without each and every failure contributing as they did in important, incredibly specific ways, my business would have failed a long time ago. I wouldn’t still be a writer today.

Last week, I was bowled over by the response I received from my 3,800-word year-in-review post that explored some key lessons that I learned over 38,000 miles of travel in 2013. The points that resonated the most were ones that encouraged you to “do” for the sake of doing, without knowing where might lead.

This is freedom.

And freedom is a path tread in failures and successes alike–and a million degrees of each, in between.

The next time you catch yourself look up at someone who appears to have it easy and figured out, remember:

You’re only witnessing one fraction of what’s resulted from thousands of hours of struggle and hundreds of missteps, failures and fuck ups.

And even when you get there, you’ll never have it all “figured out.”

That’s a good thing, because it means your journey is always yours–you’re always one choice away from making it so.


P.S. – If you’re in the Rhode Island or New England area and looking to kick your 2014 off on the right foot, join me, Alexandra Franzen and members of The Literati Writers for a nurturing creative weekend this January 17-19, 2014–limited tickets remain and sales end this Friday, January 10th. Learn more »