A friend hit me with an unexpected question last week.
He's a talented, hardworking creative I've watched adjust and grow his career by applying a great work ethic, earnest problem-solving and a genuine dedication to his team.
"How do you do it all?" he asked.
He was referring to the intense day job, and the young daughter and family I want to be fully present for, and this newsletter, and the community I'm building, and the novel I haven't finished yet, and my weekly men’s team meetings, and the multitude of other side projects and collaborations I’m cooking on while maintaining a modest social life and squeezing in some travel, dental appointments, and the occasional haircut.
These days, he said, he only thinks about his current job, his family duties and getting the bills paid. He marveled that I had any more room on my plate.
His perception of me was that I must have more hours in the day than anyone else.
I gave him a rambling, anecdote-laden response that I won’t bore you with…
On my drive home, I was overthinking how I could have been more succinct with my answer. One word kept coming up.
Stretch.
It's a term I first heard used seriously in men's work. What can you do just a little bit more of, right now, that moves you closer to the person you're trying to become?
One small extension, with consistent direction, can provide compounded results over time. Sooner than you’d assume, actually.
Unsplash: Ian Keefe
So maybe one word is too succinct. I realized I do have a framework that I’ve been living by; I've just never written it down before.
Who? What? How? When? Why? Where?
Ah, the classic core question words. We've long been conditioned to lead with how.
And all too frequently, we use this one negatively:
Well, I don't know how to do that. I don't know how to change direction at this stage of my career. I don't know how to build an audience. I don't know how to use this tech. I don't know how to sell something. I don't even know how to start.
Obsessing over the how before you've answered the others is exactly what keeps most people right where they are. So let’s set aside the how for now.
Let’s focus on five steps:
Where. Who. Why. What. When.
Where are you now?
This is the baseline. You can't navigate from a location you haven't acknowledged. So be honest: where are you on the grid of life right now?
This one’s uncomfortable, so most of us skip it. Sitting with an honest assessment of where you actually are requires putting down the typical script of excuses, justifications and complaints you've been feeding yourself.
Put down the script for a moment. Take a breath, and look around.
Where are you in your career, where are you in your relationships, where are you showing up in your community? Where are you on the timeline, the arc of your biography; are you close to achieving the life you want, or are your dreams still beyond the horizon?Who do you want to become?
Not what job do you want. Not what title. You, that’s who.
This is a different question than most career frameworks ask. It's asking about identity before strategy. Who’s the human first, then look at the big plan.
Who is the version of you who occasionally appears when you’re feeling most lit up by the work you love doing, living the life that feels like yours, showing up even better than you hoped to have. You feel comfortable in your skin, you feel solid on your feet, you feel articulate, strong, confident, happy, connected, generous, open, caring.
Who is that? Is that the identity would you choose and how would they move through the world? Do they wear armor or linen? Do they carry weapons or flowers? Do they have values? Do they have needs? Do they have limits and boundaries?Why do you want to become that version of you?
This is the most important question in the framework. Everything else depends on the quality of your answer here.
Not the surface answer. The real one underneath it.
Why does it matter to you - specifically, personally, in the context of the life you're actually living - to become that person? …And if you don't?
A strong purpose keeps you going, even when the how gets complicated. And the how always gets complicated.
So - why are you here? Decide it. Write it down.
“I am [where you are] right now.
I am becoming [who you wish to be]
because [why this new person]
so that I can achieve [the results of the stretch; the mountain I point to below].”
Say it out loud. Revise it. Test it with someone you trust - does it still sound true, when you say it out loud to them?What are the actionable steps?
Once you know where you are and where you’re headed, and you know your who, and your why, then the what starts to become more visible. Not all of it. It’s likely a mountain so large that its peak is obscured by clouds. Still, you can see enough to get started. Name the mountain. Add it to that statement you wrote above.
Note the big moves you’ll need first. Break those down into smaller steps. You don’t need to know every step before you start, because breaking a large move into smaller ones makes it easier to make progress, and keeps you nimble when the unexpected arises.
If you’re viewing this issue on the website, you’ll notice it’s fairly bare-bones at the moment. Not much design or branding work has happened yet. A lot of white space. When I decided to start, I took a minimalist approach so I could build the weekly writing habit first, free of distraction. Over time, I’ll likely update the look and feel of it all, but for the moment, I simply need to get the message out. If I can help someone shift their thinking or simply have a better day today, that’s what matters the most right now.When will you achieve this?
Give your steps a timeline. Not to create pressure. To create reality.
The moment you put a time stamp on something, it becomes a different kind of commitment. Feels more real. Extra tip: phrase the commitment in present or past tense, to make the destination feel even more real and reachable.
Now, work backwards from your destination. If you want to be in a different place by a certain date, what do you need to do - and who do you need to be - six months prior? Three months? Next week? Tomorrow morning? Plot it out.
There. Now you have enough to start.
But wait!…How?
Ok, here's the thing about how.
Most of what you’ll need to know you'll figure out along the way. You have to. Because the how changes constantly as you move: new lessons, unexpected obstacles, delightful discoveries, doors that open and secret paths you couldn't have seen from where you are now. And if you ever have issues with motivation, getting to the how can happen much faster when you’re in the thick of it.
The people who wait until they fully understand the how before they start? Well, they never start. They stay busy researching, planning, preparing, optimizing, and likely complaining. All of which feel productive but none of which is real movement. How do I know this? You should see just how many books, bookmarks, tabs, notes, folders, notebooks, articles, charts, drawings, photos and more I’ve collected over the years. It’s fun to scheme, but without real-world experiments to test those ideas, it’s just journaling or scrapbooking.
Unsplash: Fiona Dodd
You figure out the how by starting. Take the first step, see how it feels. By the third step, if there’s something you’ll need to learn, you’ll get after it, because you won’t want to slow down.
One caveat worth mentioning: your destination has to be genuinely achievable. No matter how much I train for the next three months, I'm not going to become an NFL quarterback. Being conscious of the difference between ambitious and unachievable isn't a form of pessimism. It's what keeps you honest with yourself.
Ok, how’s your written statement coming. Here’s another way to look at it:
“I am [your where] right now. I am becoming [your who] because [your why] so that I can achieve [your what] by [your when]”
“How do you possibly do it all?” my friend asked.
I don't, always. It depends on the day. Honestly: the novel hasn’t been touched since I wrote the outline and the first few pages two months ago. On some weeks this newsletter gets dangerously close to not being delivered. Some days I'm fully present as a dad, rendering me barely functional as anything else. I’ve still got dishes in the sink to clean, laundry to fold and the acoustic needs to be tuned. I did get the dental work and haircut in, though.
Week after week, month after month, I keep reaching. However slowly, I’m moving in the direction I deliberately chose. I know who I am, who I’m trying to become and where I'm trying to go. I know why it matters to me. And I've broken the mountain down into steps small enough that I can take just one, even on the weeks when everything else is pulling at me.
The stretch isn't heroic. It's consistent, disciplined adherence to a direction over the long term. All along, you’ll be replacing anxiety with elasticity, flexibility, confidence.
Unsplash: Marc Olivier Jodoin
This is the kind of work that I'm building The Courageous around. Not a single moment of clarity that fixes everything. A consistent practice of refocusing, of returning to these questions alongside peers who understand your world firsthand, and will tell the truth about what they see in you. Tools, community, clarity - to give you the courage you need to go after what you want. You don’t have to do this alone.
Remember, the how takes care of itself once you’ve taken care of the rest.
If you’re feeling bold, share the statement you’ve written with me. Or if you still need help with yours, drop me a line and tell me what you're working through. And I’d love to hear what else came up for you. I read every single response.
You’ve got this.
Onward,
Kevin
Founder, THE COURAGEOUS