Like it was for many of us, March 2020 was the beginning of a very difficult period for me. As a small business owner, my slate of projects and clients were wiped out in an instant. And as a mother and partner, I was thrust into full-time homeschooling and housekeeping, while also trying to pack for our family’s previously-planned relocation to another part of the state.

To say I was reeling is an understatement.

In an effort to steady myself and to find a bit of meaning in the midst of all the chaos, I decided I needed a project. I had heard of the 100 Day Project: a global community effort encouraging people to spend 100 days creating some kind of art – any kind of art – and chronicling their progress along the way. 

A new cycle was just about to begin in April 2020. Without much advance thought, I pulled out my watercolors and pens and created Day 1: Navigating Adulthood.

I called the series 100 Days of Designing My Life. I completed Day 1 and moved on to Day 2. Day 2 turned to 3, then 4, then 5 and so on. When so much of quarantine life was in chaos, this daily practice became a lifeline for me – a routine I could count on and count the days by. 

It turned out this was true not just for me, but also for my 7 year-old who would often join me on the floor to paint with his watercolors while I painted with mine.

Then June came along and the news broke about George Floyd’s murder. The United States was on fire, and in an instant, adhering to my daily project felt trivial and self-indulgent. So much of my project was about sharing outward and narrating my experience – and as a white woman, it felt tone-deaf to keep talking. I wanted to listen instead. 

I stopped at Day 66: Constraints Breed Creativity.

In July, we moved to a new house in a new city. We navigated learning to make friends at a distance, a new school and teacher, tough safety conversations with family, cancelled holiday plans, new traditions, and a new year.

In February 2021, as my 40th birthday rolled closer, I felt called to finish what I’d started. Day 67: Giving Myself Permission was my re-entry. It felt like coming home to a part of myself that had been pushed away carelessly and in haste.

I’ve always loved frameworks, sense-making, and storytelling. As a design coach and instructor, I light up when I can help people come up with new creative solutions or approach problem solving differently.

100 Days of Designing My Life (spread out across almost 12 months of my own life) grew into a collection of 100 prompts, questions, frameworks, and inspiration to help anyone see their life and work through the lenses of innovation and design thinking. 

The hundreds of hours I spent envisioning, creating, writing, and sharing these postcards challenged me not only to make the complex feel more simple, but to bring humanity and beauty into the often messy experience of designing a life. Along the way, I unknowingly chronicled my own learning and my own life as things unfolded in unexpected ways across the lifespan of the project.

How might we all design a life we love? I hope these postcards will inspire new thinking and action for your own life. Imagine what might change for you in just 100 days.

Onward,
Ashley

DAY 1: NAVIGATING ADULTHOOD

I’ve always been fascinated by the contrast between the direction I thought my life would take and the curvy path my life has actually taken. It seems to me that managing the distance between those two lines is what makes us grownups.

DAY 3: EXPANDING OUR RANGE 

I tend to play in the same octave: my comfort zone. Don’t we all? But there are times when I’m pulled out of that octave – perhaps unwillingly! – when I realize that expanding my range is what the world needs from me. Sometimes, showing up differently helps us have the impact we yearn for. How might you play in a different octave today?

DAY 23: BRIDGING THE GAP

I’m fortunate to work with many diverse coaching clients from all sorts of backgrounds, perspectives, and experiences. But you know what they all have in common? The Gap. The Gap represents the distance between where they are (current state) and where they hope to be (future state). Often, they don’t even know how to define that future state – they just know where they are right now isn’t where they want to be (side note: I totally remember this feeling from my early days as a coaching client, too!). 

Together, we get them unstuck and clear about what they’re working towards. And then? We prototype. Adopting a prototyping mindset – being open to build one small thing to try out, test, and learn from, and then refine as you go – is by far one of the most powerful tools in our wayfinding toolkit. Prototyping helps you try out different options, see what works, and then make an educated decision about next steps based on what you learned. Prototyping de-risks big choices, because we’re not making grand declarations or sweeping changes. Instead, we’re asking, “What’s the smallest, cheapest thing I can do TODAY that will help me learn the most, the fastest? I truly believe everything – EVERYTHING! – can be prototyped. What are you prototyping?

DAY 50: INNOVATION IN DESIGN // INNOVATION IN MY LIFE 

I’ve been playing with the idea that today’s models, frameworks, and other tools can help us understand how we might design our lives in new or unexpected ways. I started Day 50 with one of the most classic design thinking frameworks, a visual that demonstrates that innovation comes at the intersection of three things: Desirability (what we want or need), Feasibility (what we can technically build or create), and Viability (what will make money or be sustainable). When we map this onto innovating for our lives, I think it creates an interesting recipe for wayfinding, too. What do you think?

DAY 80: I AM MY FIRST CLIENT

Does your weekly calendar look like mine? With multiple client projects running at once, sometimes my calendar looks like a colorful bomb exploded, with barely a moment to breathe in between meetings. A couple of years ago, a coaching friend of mine planted the seed that  before I sit down to do work for my other clients, I should make time for myself. “What if you were to treat yourself like the first client of your day?” he asked. I haven’t looked at my calendar the same way since.

What might change for you if you protected some space in your calendar for your biggest priority client (AKA YOU)?

DAY 99: NOT IF, BUT WHEN

About a year ago I put a piece of big flip chart paper on an empty, white wall and grabbed my thick markers. At the top of the page I wrote, “If my dreams came true… How would I be? What would I do?” After a short while, I’d brainstormed a bunch – listing out adjectives, emotions, and actions as they came to me.

Feeling complete, I took a step back and contemplated my list. And I saw it immediately: “IF my dreams came true!?” How about WHEN?

Language makes all the difference. How we talk to ourselves makes a difference. Your dreams can already be coming true – you don’t have to wait! “Not if, but when.” Start now.