How Seth Godin can make a 2 question Application Transformative

Seth Godin @ MIT

I recently got an email from Seth Godin about an opportunity to attend a private 80 person workshop in Hastings, NY.

The application was a simple Google form asking two questions:

  • Why do you want to attend this workshop?
  • What product or contribution are you most proud of and why?

You can see my answers to these questions below, but first I wanted to highlight three reasons why this simple form was effective and inspiring.

First, by having to critically think through the answers to these questions the applicants are essentially selling themselves on why they want to go to the conference. My friend Patrick Bell and his wife Holly use a similar tactic when when selling their ESL Software at different Christian School conferences around the world. They run a contest during these conferences where they giveaway free software to one or two luck schools. To enter, the school representative or director simply has to fill out a form with all pertinent contact info and give three reasons why their school needs this software and how they will benefit form winning it. The 99% who don’t win the free software have basically made themselves even more qualified leads for Pat and Holly – convincing themselves further that the software is a value add to their current curriculum. Both the Bell’s and Seth’s approaches speak to the power of questions.

Second, the workshop application questions were powerful to answer, even if I did not get an invite (which I did by the way). To have to think critically and creatively and get to the root of Why would I want to attend a 2.5 day workshop that averages about $1500 per day? To flesh out what I’m most proud of was equally wonderful. Too often we wallow in discontent about our current circumstances and how we haven’t gotten ‘there’ yet; instead of pausing and evaluating what has gone well, what we have made and contributed, what we are proud of, what we have shipped. It is nice – and all too often rare – to measure backwards, recognizing the value we have created, the connections and impact we have made, and the fruit that has budded.

Third, the moment after I read Seth’s email invite that went out to his hundreds of thousands of followers, I thought: “That would be awesome.” Immediately, the lizard brain kicked in. Immediately, I began having self-defeating thoughts of why I was unworthy of getting picked. Immediately, I began thinking of excuses about why I shouldn’t apply. Immediately, I began telling myself why I wouldn’t get in, why I don’t have what it takes, why my answers to his questions were fake and laughable and stupid.

For Seth and his team, making people applying adds another step of vetting to the process of curating who attends. The applicant pool is now full of people willing to dance with fear and ignore – if not just momentarily – the resistance. And I’m proud to say I danced. I was like Pat Swayze in Dirty Dancing. I applied. (And I did in fact get picked – but that’s not the point.)

Now I haven’t decided if I am able to attend (it’s like four grand!).  While I’m sure it will be great, I’ve already gained so much from just applying. Is anyone surprised that Seth made a simple two question application transformative and inspiring? I’m not. This is how it should be. Thank you Seth.

Here’s my responses:

Why do you want to attend this workshop?

Since moving to a small mountain town in the Dominican Republic, the last three years have been what Seth describes as the ‘Thrash’. In many ways I am getting a masters in “failing forward.” This thrashing in pursuit of matterful & meaningful work has taken me from a sanitized corporate life in the Midwest to the mess of relationship-building and economic development work in the West Indies.
This messy-yet-beautiful tension has left me in a place where I’ve needed to look beyond myself and re-learn the value of asking for help. Through this workshop I would like to grow in my discernment of when to push through the dip and when to cut bait and run. To discern when fear is worth dancing with and when its a healthy response to a destructive situation.
Seth has been one of my literary mentors for several years and I am confident the other Ruckus Makers in attendance will be of one mind and heart. I want to attend this workshop because I am eager to cultivate new relationships that matter, and gain clarity with regard to the dip, thrash, and dance associated with my specific work.
Above all, I am hoping that my input and voice will be as valuable as that which I receive when I attend this workshop.

What project or contribution are you most proud of and why?

I am particularly proud of the Business Accelerator Program I have built to serve the developing community in which I live. The process has pressed and stretched me in ways I could not have imaged. It has pushed me to think critically about how to teach business basics to micro-entrpreneurs from a foundation of dignity, honesty, and integrity (elements often lacking in our business communities).
Though the program may only help a few people (time will tell), the value of having to set a direction, create something, press through the dip, and ship has been invaluable. While I’m extremely proud of the program, the emotional fitness and grit gained from pursuing something matterful is what I am even more proud of.
This process of battling the lizard brain, punching perfectionism in the throat, pushing through, and shipping has set me on an impact trajectory far and above staying in my comfortable cushy corporate consulting role may not have.
Photo Credit: C.C. Chapman

Ban Sunday or Live for Monday?

Thoughts on why Sundays can suck sometimes (and how to reframe it to make them suck less).

Ban Sunday?

Ahh Sundays. The last moments of rest slip into the ether before the manic-depressiveness of the week ahead.

I was digesting my Sunday paper (aka my instapaper feed on the ol’ iPad) between sips of coffee and reflective conversations with my wife and our house-guest Josh. I came across this essay at Five O’Clock mag. This is David Infante’s take on these feelings of “imprecise malaise borne of the quivering uncertainty,” – or what our family calls, the Sunday “tummy-yuckies.” Here’s David:

“Monday’s misery is easy. It’s emails that don’t stop, treadmills that won’t start, commutes that never end. I can comprehend Mondays, and I can beat them. But I don’t understand Sunday’s anguish. How can I defeat something I don’t understand? So no matter how many Mondays I meet head-on, six days later I’ll slide headfirst into the hazy slough of Sunday despond. I’ll skate through apprehensively, wondering how I got there, and what “there” even is. It could be thebooze, or the exhaustion, or the creeping awareness that my twenties are on the wane. It could be all of those things, or none of them…

Sunday is uncertain. There’s something just over the horizon, hidden equally by the curvature of the earth and the plodding second hand on your watch. At this cusp, vacuous musings gather speed and become vast existential crises, then fracture back to mundane slivers just as quickly…”

David Infante’s religious abolitionism aside, he puts to words – albeit a bit melodramatically at times – the dreadful feelings too many of us associate with the Sabbath….

But what is it that makes us see Sundays as “the hospital bed we lay in each week, reflecting on a life lived in six days while preparing to do it all over again”?

TGIM – Thank God It’s Monday

I think there’s another way.

Another way that I’ve gotten a taste of from time to time. A taste of anticipation and excitement and expectancy of possibilities and work to be done in the week ahead. And yet the Sunday tummy-yuckies still show up and need to be actively exorcised in order to maintain sanity and do the work we are called to.

One gent I follow on the interwebz is a guy named Barrett Brooks. Who built – among other noteworthy projects – an online community called Living For Monday. In a thought provoking TEDx talk he gave at UGA, he said:

“It’s time to change the way we think about work from a mindset of TGIF, where we thank god it’s Friday and count down the hours to 5 o’clock, to one of living for Monday. And it turns out that this isn’t some pie in the sky idea; there are real people showing up to work engaged and inspired every week.”

While Living for Monday is no longer operating, the foundational questions they were living was extremely powerful – How do we shift our mindsets associated with the work we pursue from a ‘thank-god-it’s-Friday’ attitude to a ‘Freak Yeah It’s Monday!’ and crush the Sunday tummy-yuckies once and for all?

In fact he has some interesting perspectives on the matter to be continually inspired by the work that we do.

He exhorts us to do work based on our beliefs, have a growth-mindset and focus on getting better everyday (kaizen for all you Japanophiles out there), and surround yourself with great people.

As my experience would have it, I agree 100% with those suggestions. Especially the community and accountability bit of keeping great company in the form of mentors and accountability/mastermind groups (formal or informal).

All I would add is to slow down and connect with ‘why’ and the original calling.

As Barrett points out, your work becomes inspiring when it aligns with your personal/professional goals and your personal beliefs and values. (And if it doesn’t align with any of these, then maybe it’s time for a change. But that’s a different conversation for a different day). We must be clear about this goals and beliefs and values before we look for work to be motivating.

At the end of the day, our work is central to our original calling. The original command “to subdue the earth.” This means compose music, engineer computer programs, balance balance sheets, build skyscrapers, and scrub toilets.

In other words – do the dignified work your hands find to do. The work we can’t help but doing as human beings. Even if it’s not the grandest or sexiest or fun-est or inspiring-ist work you can think of. (P.S. The grass is always going to look greener when doing the grunt work)

In some ways focusing on this original call can be enough, in and of itself. This is piggybacks on Barrett’s second point of cultivating the growth mindset – we must pause, meditate on, and reframe our work in it’s toughest, messiest, or most mind-numbing moments (usually the Sunday afternoon moments), in order to view work as our original call.

To view your work – regardless of how passionate you may feel about it in the moment – as God-honoring. To view appropriately as your ministry; your offering to God and others.

I used to think that professional work was somehow second-rate to full-time ministry. That somehow I would get wow-points or be closer to God by going into full-time ministry. But I’ve come to realize Jesus is about all-world missions, and I doubt he saw any distinction between the work of the tax collector and the work of the evangelist. It is all God-given and God-inspired. It’s all “ministry” and should be viewed as (one of) our primary means to bring glory to God, advance the common good, and bring peace, prosperity, and flourishing to the community in which our work touches. Whether that’s through hanging sheet rock, bootstrapping a start-up, or providing clean water to communities in Africa really is a secondary question.

I’m not sure that we’ll ever be able to truly rid ourselves of some latent feelings of trepidation or some level of emotive hangover after a weekend of God-honoring merriment and revelry with our loved ones. But I do think there is a way to pursue meaningful work and frame your work as meaningful to inspire and motivate you to feel alive for Mondays.

While I haven’t boiled this down into some definitive actionable step or cure-all for the Sunday tummy-yuckies, I do think pausing for a moment to think on your work and God, and how He would have us view work, can go a long way in cultivating the grit and motivation to learn to love the grind.

Happy Sunday brave ones.

Go Deeper

  • Pick up Chip Conley’s PEAK: How Great Companies Get Their Mojo from Maslow for a more in depth look at what motivates employees, investors, and customers and how to thrive in and create organizations that are truly transformational on all fronts.
  • James Clear at writes a great deal about small-incremental improvements in work and life, habit formation, and learning to love the work for work’s sake.
  • Thank Goodness It’s Monday: Barrett Brooks – TEDxUGA

The Power of ‘What if?’

What if what we measured was trust?

Or dignity?

Or empowerment?

Or authentic connection?

Or the advancement of the Common Good?

What if we paused working to impacting the world?
What if we started working to have an impact on ourselves (first)?

What if our focus was off performance and onto the process?

What if we were interested in means rather than ends?

What if we focused not just on what we are doing, but how we are doing it?

What if our focus was on We(not Them & Us)

What if we fought to internalize that money is a side effect, a rule to the game (not the game itself)?

What if we lived these questions?

What if?


Playing Up

It was my first year at Miami University playing for the Redhawks (then Redskins); I had worked hard to earn a spot on the starting XV (the first team for those non-rugby-connoisseurs out there) over a senior starter, and had just been asked to represent Ohio at the Inter-Territorial Tournament in the fall. Things were looking good (and truthfully I was probably a bit too big for my britches because of these early successes).

As the season progressed the dates for the All-State team’s tournament were scheduled on the same day we had a union match for our University team. There were three of us from Miami that had been selected to the All-State team and we were now forced to make the decision to choose between our brothers in red and representing the state of Ohio. At the time it wasn’t an easy decision.

Under some well-intentioned-yet-foolish council from a former alum, myself and one other of the All-State selectees decided to stay home and play for the club rather than going to the Inter-Territorial Tourney. We chose the University game over playing up with the All-State team. The third of our All-State selectees chose to play up and go to the tournament.

I don’t remember all the reasons why we chose to stay rather than play up, but I think it was easier (read: safer) to stay in the comfort zone. To be playing with my team in a position I knew and in a game we were confident we’d win VS. playing with, and against, a bunch of other all-stars from around the midwest, where the risk (and likelihood) of failure was much higher. Fear of not performing as well, or fear of not living into the hype, or fear of being “found out” that I wasn’t as good as they thought, caused me to sabotage any successes I might of had playing up. It’s alwasys easier to be the all-star in the minors than risk playing in the majors and failing.

After our third player returned from the tournament and told us of his experience – I was convinced I had made the wrong decision. He told of how great coaching was, how he developed by playing with other great players, and how much he took aways from the professionalism of the experience as a whole.

I told myself I’d always take the opportunity to play up.

Flash forward 5 years later, I’d taken my own advice and had represented both Ohio and the Midwest on the All-State and All-Midwest select sides. I believe playing up led to my captainship and leading our team to the national stage (we took 3rd place in the U.S. for D1AA). I was able to parlay these moderate rugby successes and some connections I’d made to move to Scotland and play for The Edinburgh Academicals (or “Accies” as they are called) – in pursuit of playing at the highest level I could.

Scotland was great. I lived with some great fellas, our flat was nicer than any living situation I’d been in (we had an elevator that came right into our apartment), and my heart was satiated being around a great rugby-appreciative culture. #HappyDan

About halfway through the fall/winter season, and under a bit of peer pressure, I began playing with another – albeit, less competitive, less seasoned, and less well-coached – club. Eventually I left the first club I had been with to play for this new team. I rationalized this for a number of reasons – the biggest being that the “banter was better” and the Accies were a bit “clique-y.”

Fear of being “found out”

I could say I let banter – as great of a things as it is – come between me and my goal of playing up at the highest level I could. But after more introspection, it was fear.

Fear of failure.

Fear of not being the best one on the team (or not making the jump to the next level).

Fear of not be the biggest fish in the pond.

Fear of being “found out” that my early successes were just a fluke and I was not as good as I/they thought.

It was this fear that drove me to not push hard into playing up.

But these were all fears I had overcome before…hmm.

In both of these instances I ended up regretting not seizing the opportunity to play at the higher level. I had learned the first time but when things got a bit harder, environment and community changed, it became easy to go to where the comfort and safety was rather than pressing into the uncertain.

When presented with an opportunity to have an easier “more fun” path, all it takes sometimes is a bit of pressure to move us off our goals and away from the things we desire most. We are fickle little beings.

Tactics and questions:

Write down and regularly review your goals and enduring traits and continue to build a code of character. One of the cornerstones in my code of character is “I always play up. I learn up. I lead up. I love up. I pray up.” …in my marriage…in my business and work…in life. In other words, when given opportunities and talents do you take and used them? 

Are you seizing the opportunities around you to “play” for better coaches? Are you attending killer conferences, reading the works of great minds and thought leaders, being developed by your job, and do you have a mentor?

Are you seizing the opportunities to “play” with other all-stars? Start building your tribe. Start meeting with a like-minded accountability buddy (or two…or three) throughout the week to make sure you are staying on track with the things you say you desire most. Start building your support team and putting your goals out there to be held accountable to. Start getting plugged into other tribes and interest-groups that will be positive peer-pressure forces, going to professional developments, etc.

Are you taking the opportunities to “pray up”? Sometimes it’s hard to discern which well-intentioned, yet sometimes (often) foolish, friends to listen to. Spending quality time with and engaging God and the Holy Spirit will help you discern and direct who to allow to speak into our lives and which decisions you should be making and the direction you should be moving.

Playing up sometimes means having icky conversations, or letting people go, or sticking up for what you know to be right, even in the face of opposition. Playing up means dancing with fear and choosing the long hard road that begets perseverance and mastery. Playing up means working to align what we do with how we do it.

Good talk. See you out there,


The Art of Iteration & The Alchemy of Fear

Making art means pursuing and engaging in meaningful work.

I’ve recently been reading the Icarus Deception by Seth Godin and it has been resonating with me. What really helped me unlock the sometimes-nebulous concepts and helped me own the message was replacing the word ‘art’ with ‘meaningful work.’

Thus I’ve concluded that I am an artist. And as an artist, I gravitate to where the work is meaningful. As I am sure you do too.

As Seth Godin lays out, art and this journey in creating meaningful work is scary.

It flies in the face of the Industrialist’s notion of “safe.”

It requires tolerance of the ambiguous and the uncertain.

It requires pursuing people and connection over productivity and eking out incremental efficiencies.

It requires reevaluating and realigning one’s comfort zone (and corresponding safety zone).

It requires being vulnerable, and speaking up, and owning a message and cause.

Art (meaningful work) requires owning and embracing “this might not work” and going anyway.

The journey is messy and scary and isn’t all unicorns and rainbows. We all know this, yet it often takes time to internalize it. To let that head knowledge permeate our being.

This journey, this process, this gauntlet, is wrought with iteration. Anyone familiar with the tech startup world knows the importance of iteration –

Launch the minimum viable product you can; get it into users hands.

Watch it hiccup, and fail.

These hiccups provide data points, benchmarks and information to get feedback, find the kinks and the bugs.


Launch again.

Rinse and repeat until you’re thing is rockin’.

The thought leadership is pretty clear at this point – we need to embrace the fear of failure. Or as Jonathan Fields puts it in his 10 Commandments of Epic Business that blew up in the lifestyle/entrepreneur niche – “Thou shalt train thy mind in the Alchemy of Fear.” And they’ll all tell you that it’s about learning to be comfortable with failing (and failing often).

Which it is.

The Unsexy Failure

But I’m not sure these thought leaders take it far enough, because failure, in and of itself, isn’t that scary. We all know in our heads that failure is part of the journey to making ourselves and our work better. Let’s all agree that’s a given at this point in our post-industrialist age.

Our fear goes deeper than just failure; we are afraid of a specific type or flavor of failure (at least when it comes to the meaningful work we care about). I think Jonathan Fields called it an “alchemy” because our fear is a complex and potent cocktail of many different strains of fears and flavors of failures. I think most anyone who has started recognizes and acknowledges, at the macro-level, that there is risk of failure – it’s part of the game.

We know that if our venture fails, we still have breath in our lungs, our rainy day emergency savings is still there (hopefully), and mom and dad’s basement – in all it’s dankness – is waiting with open arms. But it’s the expectation of how failure should look, that we get hung up on. 

We tell ourselves: for failure to be successful (oxymoron?) it needs to look like this or that. We try to fit failure into a box of our expectations.

We tell ourselves: Failure needs to have these tangible leftovers and pieces for me to show off and build on and boast about.

We tell ourselves: Failure needs to have sex appeal. And the the scariest thing – the thing I’m (we?) most afraid of – is an unsexy failure. 

The Unsexy Failure: A failure that can’t be leveraged, or spun into a compelling blog post, or turned into an ebook, or humble-bragged about in a job interview at Warby Parker or Zappos or Google.

What if our thing fails and all we have to show for it is an un-sticky idea and a false start?

What if all that’s left to show is no users, a broken co-founder relationship, some unanswered cold emails to potential investors and partners, and a half-renovated office space with a termite and rat problem.

What then?

The unsexy failure. God forbid.

Jerry Colonna talks about the importance of separating your feeling of worth from the thing(s) that you do – no matter how amazing or unsexy they turn out to be. One tactic he encourages to achieve this separation is by replacing expectation with gratitude. Practically, this may look like keeping a gratitude journal. Or pausing throughout the day to meditate or thank God for the small gifts along the way and focusing on wanting what you already have. Or a slew of other ways to cultivate gratefulness. 

A matter of selfishness.

I also think this fear of the unsexy failure is a matter of selfishness. And meaningful work, by definition, is not about us – it’s about serving others in a dignified way. This fear (and fear in general?) is selfish and shows our limited understanding of failure and its role on the journey.

It’s selfish because it means my failure needs to look a certain way, all the work needing to be done needs to be tangle and quantifiable to have something sexy to serve me and my contingency plan if it all goes to hell.

We all know that the process of failing and iterating is wildly important to make the best possible thing and serve the right audience. We know that this art of learning how to iterate well is key to learning, developing, and succeeding in our ventures (and life).

Therefore, we must recognize, name, and admonish the fear of the unsexy or the ‘wrong-type’ of failure. We do this by refocusing on the people we are serving. We double-down on the community and connections we are building. Our refocus suffocates this fear. And even if we experience the unsexy failure – not all is lost.

Failures – all shapes, sizes, and flavors – are an essential part of fortifying the strong and gritty emotional foundation required for being an artists/entrepreneur/change-maker/doer of meaningful work.

Big takeaway: 1) Identify and name the specific type of failure that you’re afraid of. This is the first step to punching that fear in the jugular. 2) The second step is to refocus on the human elements – the people you are serving.

Don’t discriminate against failure.

[Meaningful work] might scare you.
[Meaningful work] might bust you.
But [meaningful work] is who we are and what we do and what we need…
[Meaningful work] isn’t a result; it’s a journey.

I would add that meaningful work – work you are called to – will be a result of failure and iteration.

A snapshot from the back cover of Seth Godin's The Icarus Deception. (It helps to replace 'art' with 'meaningful work')

A snapshot from the back cover of Seth Godin’s The Icarus Deception. (It helps to replace ‘art’ with ‘meaningful work’)

And we must train ourselves for the emotional rodeo of not discriminating against which type of failures we fear and the ones we don’t.

So let’s drop our expectations of how failure (and successes) should look and feel, and learn (re-learn, and re-re-learn) to be content with living the questions and the adventure at hand.

Sure it’s generally better to strike out swinging for the fences than watching one hum in over the plate, but the moment we try to force failure into a predefined box is the moment that creates an environment primed for fear to take root.

Meaningful work is an art – the art of iteration and of training in the alchemy of fear.

Happy hunting.

Dan LeMoine