Highs, lows, and letting go

How a hard year led me to take steps away from brand design toward storytelling.

There’s a scene in the movie 8 Mile that captures what life felt like to me a couple of years ago. One night, Jimmy 'B-Rabbit' Smith, a hip hop hopeful living a life riddled with hardship on the streets of Detroit, absolutely slays his competition in a local open mic battle. It’s a win of particular significance sure to get Rabbit the recognition needed to catapult his music career. 
But instead of a montage of milestones and further successes, after a moment’s celebration outside of the club where the battle was just won, we see Rabbit do something unexpected. He heads back to his joyless job at a manufacturing plant, leaving his friends to continue celebrating in his absence. 
Tandem, sometimes simultaneous highs and lows is what my life was full of in 2019.
At that time, all I wanted to do was brand design. I loved crafting clean visual identities that were full of meaning and void of clutter. I loved helping clients lay foundations of principles on which they could build powerfully resonant brands. My wife, Alicia, and I would lead people to see and leverage the synergistic relationship between purpose, mission, vision, and values. 
For 20 years I had worked to a dream of doing strategic brand design independently and full time, and I finally was. It was fun. It was fulfilling. And it was financially fruitless. We were broke and getting more broke by the day. 
The reality was that our brand design projects were few, and months between. Though we established a company long ago, Thinkory, and did well to share its accomplishments through the years, we never really got traction. Couldn’t quite figure it out. Our brand design consultancy didn’t have the brand perception that benefited our peers and competitors. 
At home, we were facing eviction, and not for the first time. We were living off a $2,900 loan given to us around Christmas the year before by a couple we knew. Friends who generously kept us and our two kids from potentially ringing in the new year from a homeless shelter. We were grateful for the assist and how it helped us step into 2019 with steadier legs. But the ground kept shifting. Design prospects slowed as bills flowed relentlessly. We didn’t know how we’d repay the loan from our friends let alone make rent and meet regular expenses going forward. About $3,500 every month. 
Then, just as the confetti settled on a new year of uncertainties in January 2019, an early stage entrepreneur contracted me to design a logo for her would-be fashion brand: $1,000. And an old client partner asked me to help them design a single page website for their organization: $250. Then a couple, who are leaders, teachers, and friends to Alicia and me, generously retained us as consultants for a few weeks to help them explore the idea of developing a local co-working space: $6,000. In March, a notable researcher and author in the field of family and work life contracted our consultancy to design several research papers and infographics as well as a basic website to make them accessible to the public: $10,500. 
And just as it felt as if our allotment of financial blessings surely disqualified us from receiving even one more, a full time, six-month design contract with Capital One was offered to me in April: $78 per hour, netting us $2,300… every… week.
In four months flat we went from famine to feast. We repaid the loan to our friends faster than we thought possible and thanked them for keeping us from falling over. We were running now, energized by the stream of opportunities – including the job at Capital One which, admittedly, took some effort for me to accept. 
Not long before this time, the very thought of securing regular work felt like premeditating a murder of my entrepreneurial soul. Dramatic, but it felt like someone died inside when I understood that a full time job was necessary. When I understood that I did not have the ability as a design entrepreneur to overcome the financial challenges our family was suffering. It was defeat admitted and it hurt like mad. 
The pain abated in the months and experiences leading up to the Capital One opportunity. I saw my dream of Thinkory in the context of our reality. Time and hardship prepared me to consider a change of course.
For the first time in a long time we had financial margin with the new job. We could choose what we wanted to do – give, save, spend. There were options for decisions, not just obligations dictating our movements. The design role was a 40 hour per week commitment with plenty to learn and much of it was refreshing. Like the respect and regard design principles were given in the company’s 600-person, multifaceted design team. Not something I’d ever witnessed in a corporation. 
I started to see how I could grow at Capital One as a creative professional, charting my own path toward the company’s vision of banking changed for good. I saw how design processes thrived when supported by a creative community. I saw how I could use what I learned to reinforce our struggling brand design consultancy. A rather active struggle as I continued to manage a project that demanded near full time attention itself.  
The core tasks of the research paper design project were simple enough: design a template for eight research papers, create eight infographics surfacing key insights from each paper, and develop a simple website to make these resources freely accessible to the public. The project also afforded the opportunity to hire a couple of designers to help. That was an important first for me. I’m better suited to guide the creative process and leave hands-on design to better skilled professionals. I figured this would give me a chance to practice playing that part. 
We brought on two designers, one to focus on the research papers while the other, a good friend, created the infographics. If neither designer could also take on designing the basic website, I’d handle it since that was to be the lightest lift. All straightforward. All, that is, except the working relationship with our client partner. 
Though we began with the usual artifacts of alignment – statement of work, working agreement, creative brief – Alicia and I were discovering new goals and requirements well into the design process. As the work began, I seemed to be incapable of getting a clear understanding of anything. From when we’d start, which resulted in a delayed kickoff, to what we were actually being hired to do, nothing I heard from our client partner made much sense. It was as if a cloud of confusion constantly hovered above my shoulders whenever I engaged the project. I didn’t know what I was doing though I’d done this kind of work for two decades. Thankfully, as the anxiety grew and the pressure built, a welcome reprieve was coming.
If in the layers of my life, these things I’ve mentioned could be considered the foreground activities of 2019, then for several months, I had been preparing for the greatest experience of my year – and career – in the background. By the grace of God and with the kindness of several family and friends, I raised $2,500 to fund a kind of missionary work trip to Europe that would take place in late July. 
For seven days, I’d help coach and encourage some 200 overseas missionary families who were gathering for a conference (and a respite) in Tallinn, Estonia. I was going as a Design Ambassador with The Good Story, a nonprofit that helps missionaries creatively communicate Kingdom stories by pairing them with believers in the professional fields of art, design, and tech. Leading up to the trip, our small team of five met regularly to plan the group workshops, private consultations, and intimate lunch-and-learn experiences we’d facilitate at the conference. We cherished the unique opportunity to use our collective talents, skills, and experiences to help these champions of the Faith learn to tell their stories and raise support for their work more effectively. Funded and ready, we each left our families home and got started in Tallinn.
The work at the conference was hard with early morning consults, late afternoon events, and a restless sun that seemed to refuse to settle on the horizon. There was much to do and nearly no margin available to explore this new part of the world that I had never seen. I was busy, stretched, and deeply tired. And through it all, I had never felt more satisfied and fulfilled as a creative professional.
The missionary families we met, ate with, listened to, taught, and learned from were nothing short of amazing. Beautifully ordinary humans doing extraordinary things. Sacrifices to comfort and safety that they willingly made out of God’s love and for the good of others – even hostile others – all across Europe. It was a great challenge to be the furthest away from home than I had ever been, but I found myself conflicted at the conference’s end. Desperately, I wanted to get back to my family. Simultaneously, I desperately wanted not to leave the new family members I’d gotten to know. Mine was the great honor of serving them. A great but most worthy draw on my time and energy.
Back in the US, I returned not just to the love of my missed family, and to the wonder of my promising role at Capital One, but also to the budding anguish of the research paper design project. An experience that was not getting better.
The project continued to be hindered by a perpetual sense of misalignment, disrupting the team’s flow of creative production. Everything, and I mean literally everything we did was a guess. I was leading our team to take their best shots in the dark at a target I understood less and less. For four months my sense of what was needed dulled with each awkward, anxiety-inducing interaction with our client partner. In time, my focus shifted from producing objective design solutions to serving the subjective satisfaction of one person – and still nothing we did hit the mark. The client grew increasingly frustrated with the lack of progress until, ultimately, in November 2019, I was fired.
For the first time in my 20-year career as a creative professional, a client fired me. I was summarily dismissed with an email and without an opportunity to sway the decision. It was over. I had failed.
The release was bittersweet. As unfortunate as the outcome was, I could begin to put the experience behind me with just one more step. I needed to share the news with my team. 
I decided to be totally honest about what happened. My inability to understand and satisfy the client’s basic needs led to the project’s downfall. I wasn’t entirely to blame for that, but I focused on my share as I spoke with them. 
Alicia and I decided to satisfy their contracts in-full despite them only being able to complete less than half of the work. We felt like that was important somehow, to act out of an appreciating love in the midst of misfortune. To practice that when it wasn’t easy. Our designers understood what happened and appreciated the gesture. I could move on, though my footfalls were heavy. 
The impact of the failure lingered for weeks. I didn’t know what to make of the experience. I didn’t know what it meant for me or my career as a designer. An unhealthy doubt about my capabilities began to fester and no counter thought would remedy. Not everything was wrong in the wake of the project. The contract role at Capital One went permanent – less money but more benefits. Our family would celebrate Christmas more abundantly than we ever could before. And of course, we all had our health. Still, I couldn’t get right.
As the year wound down, I wanted to better understand what happened and why it happened. Stepping back to see more of the picture, I began to notice a few things that contributed to the fail. 
The first was that I had desperately said “yes” to something that should have heard “no.” I didn’t look hard for discernible indicators of a misfit in early conversations with the client because I didn’t want to find them. I was desperate. I was driven by the desire to quickly and certainly distance our family from the financial hardships we had been enduring. I was too eager for relief to earnestly seek, wait on, and trust God with the prospect. I’m not saying I didn’t pray for guidance, but it was kind of like an interviewer asking a question and then leaving the room before the interviewee had a chance to respond. I didn’t really want to hear the answer for fear it would have been “nope, not this one.”
The second was that I set myself to serve too many masters at once. The rough course the project had taken was not uncorrectable if I had adequate time and attention to offer it. But I was overcommitted. Between my job at Capital One, preparation for the missionary work trip, and this research paper design project, nowhere was I 100% present and engaged.
There was intrigue to the third thing I noticed. I had in some part said yes to this project because I was holding tightly to a dream of design entrepreneurship. A dream that I honestly wasn’t sure mattered to me anymore. I hadn’t bothered to check. Maybe I was afraid to. Maybe ignorance was bliss. Whatever the case, I was now motivated to reexamine the dream. I was ready to ask God and myself what of my work truly mattered to Him and to me. And this time, I would await the answer. 
In the last couple weeks of 2019 I made the difficult decision to stop accepting new independent design projects indefinitely. I used the margin that freed up to enter into a time of seeking. A deep, needed period of introspection. 
Alicia lovingly encouraged me through the season with active listening, frequent conversations, prayer, and making sure I had the space I needed to contemplate. Without complaint, she’d pull double duty with our two homeschooled kids compensating for me wherever I momentarily fell short of being Dad. I do not deserve her.
A big fan of audiobooks, I went for long walks in our Northeast DC neighborhood while listening to “Essentialism” by Greg McKeown and “Master of One” by Jordan Raynor. God used these books to guide me through an examination of myself, my purpose, and my work. To ascertain what was there, identify that which was no longer valuable, and discern what was missing.
I found myself in Essentialism. The ideas around a disciplined pursuit of less, but better, immediately and totally resonated. Greg McKeown’s words awoke a courage in me that long lay dormant. The courage to say “no” to the unessential, to resist the momentum of mediocrity, and to trust God with the reputation such choices may shape. 
With this new courage I would decisively narrow my focus to make the highest contribution to the things that really mattered to me. To that which was essential to what I understood to be my God-given purpose. But was my work as a designer or my entrepreneurial dream truly serving that purpose? I found clarity through a revolutionary experience with the next book.
Following the prompts in Jordan Raynor’s Master of One, I reconsidered my purpose and dissected my dream to build a DC-based brand design consultancy filled with engaged creative professionals working with brave founders of impactful brands. I closely inspected the parts of that vision, holding them up to the light of God’s Word to examine them through the lens of the life He brought me through in the last year. Nothing was held certain or assumed verified. And while my purpose, “to make Hope visible,” held true as a still valid extension of my gift of exhortation, how I went about serving that purpose remained a question. 
By March of 2020, a Google Doc roughly 17 pages and 8,800 words long explored that query. It held my most honest thoughts to date about myself, my purpose, and my work as a designer. 
I co-labored for weeks with God's Spirit to work out what I would choose to master for His glory and the good of others. It was a time of getting alone with God and the contents of my heart to deeply understand where I was and where I was going. It was a time of learning that the work I did was a choice and that I, thank God, was privileged to have options. I didn’t have to hold on to my dream as it was. I could allow it to evolve and mature. I could allow it to be taken from my hands as I held it before God. And that’s what was needed.
In that release, letting go of my dream, I found something new. Something I needed to see but wasn’t willing to look at on my own. I found an insatiable curiosity for storytelling. 
For about the last 15 years, I low-key wanted to tell stories that moved people like they had masterfully moved me all my life. From page turning comics and graphic novels to epic serials and movies, I wanted to be a practitioner of that work. I was just afraid to admit it to myself and commit to the interest. Afraid to risk rejection and look foolish. Afraid to make the wrong choice and fail needlessly. Afraid to hit the reset button on my career after so many years of hard work in one direction. 
To begin all over again seemed irresponsible and reckless. No way I could entertain such a radical change to my life’s work. No way I could deviate from my vision for Thinkory. No way, but for the sobering flood of high highs and low lows I experienced in my profession in 2019. Experiences that catalyzed a period of introspection and allowed me to get needed perspective on the truth of things. 
I had been rejected and no one thought I looked foolish. They understood and held me up. I had made wrong choices that led to failure and it wasn’t needless. It made me wiser and more aware of what mattered most. 
And who was I kidding? I had already hit the reset button on my career to head in different directions so often that the springs were nearly worn out. I’ve pivoted from one design discipline to another – from graphic design to web design to product design to brand design. Without fail, God carried the good of each experience into the next. He used them all to render the fearfully and wonderfully made man He always envisioned. 
With that, I had decided. My chosen work to master would be storytelling. 
Alicia was the first to know and celebrate the choice. My good friend, who failed with me on that design project, was the second. His classic Memphis reply was as profound as it was succinct, “Yeah, that makes sense.” These people knew what I didn’t want to. And, like God, they patiently waited for me to get there. 
When I did, a new crop of opportunities sprang up and worked in service to mastering storytelling. One of those opportunities was a chance to redefine my role at Capital One. 
Originally, I was hired as a communication designer on a team where crafting communication experiences for our associates felt out of place. Now I was being invited to join our Vice President’s new Chief of Staff team where internal communications would be given proper focus. In this shift, I was asked to rewrite my job description. 
As a new essentialist, I wanted my role to accurately reflect what the team needed, what I actually did, and what I really wanted to do. With confidence, I set the essential intent of my role: “To ensure the right stories are told to the right people at the right time and in the right way.” I expanded on that statement with a clear summary of my work and a very shortlist of essential functions. Thinking hard about how I wanted my role to be perceived and understood, I invented a new job title: “Story Strategist.” It was a risky move. The innovation could have lost me needed support for the way I thought about this new role, but I was primed to take the chance.
I was ecstatic when I got the news that our VP had read and happily approved the job title and description I had written. It gave me the endorsement I needed to help our people thoughtfully tell the stories of their work in ways that could move people to desirable action and refine the shape of our working culture.
Today, as I take slow and deliberate steps toward a mastery of storytelling that would enable me to write and direct feature films, I’m crafting great stories of impactful work at Capital One as a Story Strategist. With every new opportunity, I’m learning how to consistently serve, as Jordan Raynor says, through the ministry of excellence for God’s glory and the good of others.