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About two years ago, I read Your Money or Your Life, and I had trouble answering one of the core questions of the book. “What would you do if you didn’t have to work for a living?” was a question that stumped me. 

I hadn’t thought about what I wanted in so many years that I didn’t know who I was anymore. I couldn’t tell you the last time I engaged in a hobby that I enjoyed. I was working a toxic job. I felt like all I could do was go to work and recover from work. 

Starting to reflect on this question was a real wake-up call for me.

I tried many strategies. Meditation, journaling, and reflection helped me to reconnect with myself. I started to remember what I enjoyed doing and began focusing my time on some of those things. 

I started being more intentional about setting goals and creating habits to make my life happier.

But, I wasn’t dreaming big. My dreams were still small and manageable. They were things I was 100% sure I could achieve.

It wasn’t until the past 6 months where things have finally clicked. 

Reading Designing Your Life

Last summer, I finished reading the book, “Designing Your Life.” The book was helpful and gave me some new perspectives and ideas. This is where things really started to take shape for me.

This book is based on the idea that you can use the same principles of design thinking to design your life. This is the same process that designers would use when designing a new product. The foundation is that life is not about getting to a “successful destination.” Instead is about the journey – about growth and change.

Before reading this book, I took an approach of focusing primarily on thinking and reflection to figure out what I wanted. Knowing yourself and what you enjoy is important. Yet, this book embraces the idea that “Designers don’t think their way forward. Designers build their way forward.” (XXV)

We’re not going to wake up one day saying we are passionate about something and want to do that for the rest of our lives. According to the authors, “Passion comes after [you] try something, discover [you] like it, and develop mastery – not before.” (XXIX)

So, how do you figure out what you are passionate about and “build your way forward”?

The book takes you through a variety of activities to figure out who you are, what you believe, what you want to do, and how you can get there.

The activities included:

  • Determining your level of satisfaction in different areas of your life.
  • Defining your Workview and Lifeview – the purpose of work and of life.
  • Tracking your energy and engagement to see what daily activities engage and energize you and which drain you.
  • Identifying peak experiences.
  • Brainstorming and mindmaps about all kinds of options that could be available.
  • Creating 3 “Odyssey Plans” – creating three 5-year plans for yourself. These three plans should be:
    • Life 1 – the thing you plan to do.
    • Life 2 – what you would do if Life 1 were no longer an option
    • Life 3 – what you would do if money were no object
  • Determining ways to prototype (test out) each option through conversations and experience
  • Take action, reflect, and build your way forward. 

This process helps us learn to “build our way forward.” We should determine our path based on action and reflection, not just reflection. 

The Power of Accountability When Designing Your Life

The last chapter of the book recommended putting together a “design team.” This is a group of people who are committed to designing their own lives and want to support each other in the process.

I decided to give it a try.

I had no idea that putting together a group would be such a transformational experience. 

Last summer, I reached out to the personal finance community on Twitter. Within a day, our group of 4 (me, Ms. Mod from Modest Millionaires, Barista FIRE, and Lacy from Sense with Cents) was filled.

Over the last 6-8 months, our design team has met monthly. To prepare for the meetings, we read a chapter and went through the various activities as pre-work. Within the sessions, we discussed our learnings from each activity. Then, we brainstormed together about ideas for each person. 

This simple process has completely changed my outlook on life. I’m now dreaming bigger than ever before. I’m also experimenting with different paths to achieve these dreams. 

The Activities Had a Powerful Impact

Each person in the group experienced a personal transformation. I want to let them share in their own words. 

For me, the activity that had the biggest impact was the brainstorming and mind maps. First, we reflected on our peak experiences and tracked our energy and engagement. Once we reflected on the commonalities between these experiences to create mind maps. The mind maps were broad brainstorming on specific things that provided us energy, engagement, and flow.

I’m a fairly pragmatic person. I tend to jump to conclusions about whether things will work (or not) pretty quickly. Because of this, I can sometimes stop my own brainstorming before getting started. This process arrested that reaction and allowed me to think big. 

When we later went into the group brainstorming, the team helped me think even bigger!

Lacy found the process of documenting our Workview and Lifeview extremely powerful. Lacy says,

“The initial process of documenting our Workview and Lifeview provided the lens through which every current or potential life choice could be evaluated. All throughout the process, I continued to check back in with my Workview and Lifeview. This helped me to filter my choices so I was always left with the very best ones for me.”

For Barista FIRE, creating the three life plans (Odyssey Plans) was also the most valuable. She says,

“We were supposed to design three potential lives. One is the life you are planning. Two is if that plan is no longer an option. Three is if money were no object.


I named my ‘life 1’ corporate drone and investor. I think that’s very telling. If you name something so negatively, it shows how much you dislike it. I realized I hated being a corporate drone. While researching people to interview about my ideas for lives 2 and 3, I realized that there were people were living these lives. If they could, why not me?


I realize I don’t have to be a corporate drone to live. There is life beyond the nine-to-five. As far away as my ideas for lives 2 and 3 are, this activity made me realize that they are possible. I could be living them if I want to.


Life feels less bleak now. I am hopeful and excited. I don’t know yet how I would generate income in lives 2 and 3. Having these ideas makes me feel so happy and at peace even though I’m on the verge of losing my corporate job. It’s almost as if that part of me that I have so long denied is finally coming awake.”

The thing that was most impactful for Ms. Mod was the feedback from discussing ideas with the group.  She says,

Bouncing ideas off of people in various fields was quite illuminating. It helped my aspirations become concrete ideas. It was also inspiring to see others doubt themselves and work through those doubts to better define a life that would be more satisfying. Brainstorming ideas that are near and dear to your heart with a small group of passionate people is such an enriching process.”

This Process Shifted Our Mindsets

We all saw many mindset shifts while participating in this group. 

For me, the broad brainstorming and creating the three life plans allowed me to dream bigger. I felt like I was already thinking somewhat big by choosing to work part-time and run my blog on the side. I’m enjoying this now (for the most part), but lifestyle design is never finished. My first life plan had me continuing to pursue my part-time job and continuing to grow my blog. At some point down the road, I would see if I could generate enough income to quit my job and become semi-retired. 

digital nomad computer ocean
Who knows? Maybe I’ll be doing work from this desk someday!

My third life plan (the one where money was no object) really got my jazzed. In this plan, I brainstormed about ways that I could combine my passions for teaching and coaching with a balanced life and my love for travel. In this life plan, I run a location-independent coaching business. Eventually, I run lifestyle design and FI retreats in different parts of the world as we slow travel. While I don’t know how these plans will evolve as I “prototype” and build my way forward, I’m excited to be working toward them. 

When I asked Barista FIRE what she got out of the process, here’s what she shared.

I realize that I don’t have to put up with a subpar life for financial freedom. I can design a life I don’t want to escape from. I’ve spent far too long living life on other people’s terms and have put up with a lot just to get money.


Being part of this group has given me permission that I can embrace a life that is riskier and less conventional for my happiness. Now that I’m facing a job loss, I find that I’m feeling positive about it. Yes, I’m scared, but I’m also excited. I have so many ideas for things I want to test out. I contribute this change of mindset to being with like-minded folks in this group.”

From Ms. Mod, we heard,

Before participating in the group, I had a lot of aspirations that I put on hold. I did believe it was important to find happiness along the journey to FI. Yet, I had the idea that I needed to find happiness in my current circumstances only. The projects I wanted to do would have to wait.


Working with this group helped me realize that I can make many changes in my life now so that I can also pursue my passion projects. I have so many ideas. It’s a matter of taking action and testing my ideas to make informed decisions. There are ways to structure my time to support finding my passions and building something now rather than waiting to reach FI.”

Lacy also shared how participating in this group changed her mindset.

“I’ve always had the confidence that I could design a life I wanted. The magic of this book and group is that I now feel like I have the tools to do so. It’s too easy to find myself on one extreme or the other – either terrified to take the leap or taking the leap too quickly without understanding if this is the right path.


This process allowed me to ‘try on’ aspects of a new life, like trying on shoes to determine the perfect fit.


This experience has also been instrumental in helping me to develop the path along my chosen journey. I used to focus too much on the destination. For me, a well-designed life includes designing all the things along the path too.”

I Want to Help You Design Your Life

What I learned from running and participating in this Designing Your Life group was that I want to help others design their lives. Meta, I know, right?

Over the last two years, I’ve gone through a process of personal transformation. From being completely burned out in a toxic job to figuring out how to live a life I love today. I am also working toward an even better vision of the future. In this vision, I get to combine my unique passions, strengths, and desires. 

I know that I’m a teacher and coach at heart. I don’t feel like any learning process is complete until I can turn around and share what I’ve learned with others.  This is why I started blogging! I wanted to share my experiences and to have an impact within the FI community. 

Through sharing my experiences on the blog, I’ve met so many people in similar situations. I’ve met people who want to dream big, have more clarity about what they want, and understand how to work toward their vision for the future. 

I feel like sharing my story through the internet isn’t enough. I want to do more.

A number of people over the last year have asked if I would help them design their lives. Because of all these things, I have decided to launch a small group coaching program. 

I’ve already started collecting feedback on what would be most helpful for people in group coaching. Based on this feedback, the group would cover the following themes (including some from the Designing Your Life book):

  • Identifying what you uniquely value
  • Strategies to figure out what you want in life
  • Brainstorming big dreams
  • Prototyping and testing your ideas
  • Overcoming barriers that might hold you back

Depending on where people are in their lifestyle design journey, we will dive deeper into different themes. 

I’m thrilled to finally share my plans with our full community.

I’m still collecting feedback to design the coaching program and will plan to launch it sometime within the next 4-6 weeks. Because I will be doing small group coaching (likely groups of 4), availability will be very limited.

If you are interested and want to be the first to learn about new developments in the coaching program, please sign up for our newsletter. Anyone who signs up with the form at the bottom of this page will also join my VIP coaching list. I will share updates and announce the launch of the program to this group first. 

I will leave you with one of my favorite quotes from the book.

“When you remember that you are always playing an infinite game of becoming more and more yourself and designing how to express the amazingness of you into the world, you can’t fail.”

I encourage you to figure out how you can design your life along the path to financial independence. There are so many strategies to do this. If you want to take your life planning to the next level, read this book, pull a group of like-minded folks together, or join one of my coaching groups.

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