Home Interviews Charlie Gilkey, Founder Of Productive Flourishing

[Interview] Charlie Gilkey, Founder Of Productive Flourishing


Charlie Gilkey is an author, entrepreneur, philosopher, Army veteran, and renowned productivity expert. Through his consulting business Productive Flourishing, he helps professional creatives, leaders, and changemakers take meaningful action on work that matters.

He is author of the new book, “Start Finishing: How to Go from Idea to Done“, for which thought leaders such as Seth Godin, Dan Pink, Jonathan Fields, and Susan Piver have given rave reviews for its invaluable approach to project management. 

Tell us a little about your eclectic background.

When I started Productive Flourishing, I was pursuing a PhD in Philosophy — I’m an ethicist and social philosopher — while simultaneously serving as an Army officer. Many people see that as eclectic, but it feels normal for me and is a direct product of my upbringing. I’m an Eagle Scout and come from a military family, so joining the Army was a natural choice for me. I’d also been reading philosophy since I was 13, so continuing to study that in college and grad school was pretty natural. The most unnatural choice for me was to become an entrepreneur. Actually, it wasn’t something any of my friends or family did and I fell backward into it.

There are a lot of books on productivity out there. How is yours different, and what makes you uniquely suited to write it?

Too many productivity books fail to address the root causes of what keeps people from doing their best work and living their best life. They tend to focus on the task-level perspective, with the result that we maybe get faster and better at getting tasks done, but those tasks don’t necessarily add up to the change-making projects that bridge the gap between our current reality and the life we want to live. “Start Finishing” is different in that it calls out the transformative ideas our souls yearn to do, shows how to convert them into projects, and then walks through the full process of pushing them to done, including addressing the natural challenges that come with doing that type of work. I call this type of work “best work.”

I’m uniquely suited to do it because it’s an outgrowth of the work I’ve been doing for the last 15 years and the book contains processes that have been field-tested and proven to work. The book isn’t about what works for me, but rather what has worked for tens of thousands of people.

Why is there such a big gap between the way we want to live our lives and our day-to-day reality?

The gap is actually illusory. There are five universal challenges that push the vision we have for ourselves and our day-to-day reality apart. Those five challenges are: 1) competing priorities, 2) head trash (i.e. the limiting beliefs, negative cultural scripts, and negative self-talk we all have), 3) no realistic plan, 4) too few resources, and 5) poor team alignment. Doing your best work will require directly confronting those challenges.

For instance, if you don’t believe you’re capable of being a good leader (head trash), it’s hard to start a business or non-profit, or run for office. In a similar vein, if you haven’t squared the (potentially) competing priorities of security and autonomy, it’s hard to fully commit to becoming a freelancer or starting a business.

How does committing to live in what you call “Project World” actually liberate us?

Project World is the idea that our lives and work each evolve every three to five years. We move, get into and out of relationships, and bear witness to significant changes to people in our lives every three to five years. We change jobs, get promoted, start businesses that evolve, or start and finish significant projects every three to five years, too.

The upside of leaning into Project World is that it removes the navel-gazing and thrashing that many people fall into around making sure they’re doing the (one) right thing. If you choose the right project and see it through, you’ll be moving on to something else in three to five years. If you choose the wrong project and drop it or see it through, you’ll be moving onto something else in three to five years. The worst choice is to stay stuck on the sidelines while you figure out what the (one) right move is. 

The downside to Project World is that you actually have to finish the projects from that phase of your life or work to build that bridge into the next version. Half-working and not-finishing something doesn’t get you there. Those who ship, win.

Why don’t people work on the projects that help them to thrive?

Here’s the thing: The more something matters, the more you’ll thrash with it. “Thrashing” is what I call the meta-work, flailing, and emotional labor we put into projects that doesn’t actually get them anywhere. Few of us thrash and have mini existential crises about taking out the trash or doing the laundry — we do them or we don’t. But when it comes to doing that work we’ve hidden in the closet of our souls until we have the time, money, connections, or whatever we think is missing, head trash (and the four other challenges) kick in and we start wondering if we have what it takes, if we’re ready, or if we’re the person to bring that idea to life.

And it’s not just that we’re scared to do our best work and fail. We’re also afraid to succeed with it because of some of the no-win scenarios we tell ourselves. These no-win scenarios come in different variants — for instance, the “success will wreck my relationships” version leads entrepreneurs who are parents to worry that their success will estrange them from their kids. The “success versus virtue” version leads creatives to worry that success means selling out. In each case, we try to navigate the downsides of success while simultaneously avoiding failure.

Threading that self-imposed needle inevitably leads us to a grey mediocrity where we’re neither winning big nor failing big. Over the course of years or decades, that mediocrity becomes ever more frustrating, especially as people who had the courage to focus on their best work start lapping us.

What are the five keys to doing our best work?

I’ve already mentioned one: Courage. But all five together form the handy mnemonic IABCD: Intention, Awareness, Boundaries, Courage, and Discipline. Most are self-explanatory, but I’ll highlight Boundaries because we too often think about them as they relate to social boundaries — what we will and won’t allow people to do to us. Boundaries can be much broader and more significant than that, though. For instance, many people aren’t doing their best work simply because they haven’t firewalled enough of the 90-minute to 2-hour blocks of time that it takes to focus on and complete that type of work. Creating those types of blocks and using them is boundary-setting.

Can we leverage the principles of “Start Finishing” that apply in our professional lives to our personal experiences and relationships?

The principles from “Start Finishing” work equally well for economic work (professional work, career work, business work, etc.) and for the work of our lives. I’m explicit in the book that anything that takes time, energy, and attention is a project, and the work of our lives should be a part of the small list of projects we commit to. Too many people focus solely on making a living while their lives pass them by and that becomes their chief regret.

Life is precious and short and we become the people we want to be by doing the work it takes to get there. It’s best to start finishing the work of our lives today rather than waiting for some better time. 


You can reach Charlie Gilkey on Twitter or Facebook. You can also check out Gilkey’s consulting business ProductiveFlourishing or find out more about his book here