The man in the arena
Chronicling the personal and professional failures and successes building a startup
My name is Philip MacDonald and this is me daring greatly. About every other week, I plan to write about user experience design, personal growth, professional growth, and experience working at a startup. If you like this article or are curious to hear more, I’d love it if you subscribed! And if you’re feeling extra generous, tell some friends.
In 2020 I joined my brother Peter and his business partner Joe, to help build Wunderite, an insurance automation platform. I brought with me six years of Product and Design experience that I learned from previous work at established software companies. It has been stressful, exciting, and the adventure of a lifetime.
Before transitioning to Wunderite, I felt like my career had plateaued and that I wasn’t being challenged at work. Likewise, I was discontent in my personal life, stuck in a loop; the same dull movie I’d seen a thousand times over.
We had an ultra-lean team in the early days of Wunderite. I was the first full-time salaried US employee. We also had two overseas engineering contractors and one part-time QA engineer who we couldn’t afford to bring on full-time. In order to handle the stress and demands of working with a lean team, I became very serious about putting my personal life in order, resulting in an upward spiral of personal and professional growth.
It’s a special opportunity that I feel blessed to participate in, especially alongside my brother Peter. Working with family can be challenging, but it affords me a consistent voice of encouragement who is also unafraid to tell it like it is. Peter has been suggesting that the cultural best practices that I advocate are worth sharing publicly, urging me to publish my ideas on Twitter, in a newsletter, or somewhere similar. Which is where Substack comes in…
Radical transparency
There’s a concept in the software industry (and elsewhere) popularized by Ray Dalio called “radical transparency,” where people and organizations openly share ideas that may have traditionally been considered trade secrets. Financial goals, internal processes, design principles, codebases, knowledgebases, and release notes are made public, signaling:
I'm confident in my abilities.
I'm not afraid to make mistakes and own them.
I'm proud of my work.
This is a collaborative effort and we can collectively do better by being open.
Think of it as the equivalent of shedding your sweatpants and loungewear, putting on a pair of pants, and making yourself a presentable but fallible participant in the world. Radical transparency can be scary and it doesn’t guarantee financial success. But at a professional and personal level, it comes with a few benefits:
Transparency forces you to solidify, define, and articulate your vision.
Transparency is a great way to make deep connections; let people know “I’m not performing, this is my authentic self.”
For companies, transparency can be a boon for meeting great collaborators, recruiting star employees, and selling to people who can truly benefit from your product.
Transparency is a creative brainstorming exercise; the process of articulating your vision helps uncover new ideas and connections.
Transparency is a great way to market test your ideas. You shouldn’t be beholden to public opinion, but disclosing your fundamentals can serve as a test of whether people gravitate to your message or if your idea stinks.
Why here, why now?
It’s a strange time. Many people are living in their own virtual reality. It’s easy to make snap judgements about people when their lives seem so public. In reality, we only get the soundbite version of a person’s story when we hear about it through social media or the news. A lot of people are hurting or withholding a part of themselves that they haven’t sorted out yet. Even talking to someone face-to-face barely scratches at the depth of a person’s experience.
That detachment between perception and reality motivates me to tell my own story. Own the narrative. Don’t sit back and let someone else write my life’s story. I want people to know me for me. Not someone else’s interpretation of me.
Historically I’ve been private and soft spoken; hesitant to open up to people I felt hadn't earned my trust. A side effect was being frustrated and angry that people didn’t understand me. In reality, I don’t think I quite understood myself. How could I ask others to understand me if I didn’t understand myself? Why would someone trust me if I’m reluctant to extend the same gratitude?
Trust is a two-way street. I suppose I’m trying to make the first move through radical transparency. Stories are powerful and if you can tell a good story, it can be the motivating factor to drive connection and inspire people to action.
Daring greatly
I considered a handful of places to house my ideas. Historically I would have opted for total control and spent days engineering and configuring my own blog on my own server. Ultimately the allure of using a service where I could own my mailing list and focus on writing led me to Substack. Ironically, I spent a lot of time agonizing over settings in Substack. One area that had me stumped was a name. After a bit of thought I landed on “Daring Greatly.” It’s a reference to President Theodore Roosevelt’s famous A Citizenship in the Republic speech (Brené Brown also quotes it in her 2012 book Daring Greatly), which he delivered in Paris, France on April 23, 1910. An excerpt reads:
Let the man of learning, the man of lettered leisure, beware of that queer and cheap temptation to pose to himself and to others as the cynic, as the man who has outgrown emotions and beliefs, the man to whom good and evil are as one. The poorest way to face life is to face it with a sneer. There are many men who feel a kind of twisted pride in cynicism; there are many who confine themselves to criticism of the way others do what they themselves dare not even attempt. There is no more unhealthy being, no man less worthy of respect, than he who either really holds, or feigns to hold, an attitude of sneering disbelief toward all that is great and lofty, whether in achievement or in that noble effort which, even if it fails, comes second to achievement. A cynical habit of thought and speech, a readiness to criticise work which the critic himself never tries to perform, an intellectual aloofness which will not accept contact with life's realities—all these are marks, not, as the possessor would fain think, of superiority, but of weakness. They mark the men unfit to bear their part manfully in the stern strife of living, who seek, in the affectation of contempt for the achievements of others, to hide from others and from themselves their own weakness. The role is easy; there is none easier, save only the role of the man who sneers alike at both criticism and performance.
It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better.
The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, and comes short again and again,
because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows the great enthusiasms, the great devotions; who spends himself in a worthy cause;
who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who know neither victory nor defeat.
There’s no shortage of critics in the world. In my case, I’m my own worst critic. When my internal critic gets mouthy and tells me that I’m no good, I’m defined by my mistakes, and I should keep quiet because people don’t want to hear from me, I remind him: “I’m the one in the arena. I’m out here doing the work, not you. So take a walk.” (My internal critic was raging leading up to publishing my first email newsletter).
For further reading, check out the first article I published on Substack (originally posted as a Twitter thread @philipmacd):
