Classes / Lives Well Designed

A Path Toward Clarity: My Journey with Designing Your Life


by admin

Life has a way of presenting us with unexpected twists and turns,

challenging us to redefine our paths and priorities. For me, this journey of introspection began earlier this year, two months after I left my job. I found myself at a crossroads, navigating the roles of spouse, mother to two elementary school-aged daughters and a daughter to a mother battling a terrible disease. It was a time of deep reflection, where I pondered what my next chapter should look like. In fact, this would be the first time I have not ‘worked’ since I was 15 years old!  Is NOW the time for me to explore a professional career that is different from what I had done for the past 18 years?

As a person who tends to approach life with caution, I’ve always been deeply analytical and thoughtful. But in this moment, I wanted to challenge myself to think beyond my usual boundaries and linear career trajectory, to embrace a more holistic perspective, and to avoid the trap of overthinking that can lead to inaction. Easy, right!?

The “Designing Your Life” (DYL) Digital Journey came into my life as a timely opportunity. I had purchased the DYL book and workbook years ago while on maternity leave, yet life’s busyness had prevented me from fully immersing myself in it.  With more time available to me now, I made a conscious decision to sign up for the digital journey. My goal was clear: I wanted to leave the workshop with a newfound clarity about the next chapter of my life, both personally and professionally. I wanted a process that would allow me to think in unconstrained, unbiased ways while still being practical to implement.

Right from the start of the workshop, I was hooked. The Fieldbrook Advising facilitators – Joan Cheverie, Michael Cato, and Catherine Dalipe – led with authenticity, curiosity, and kindness. They created a safe space for us to explore our thoughts and dreams. What also struck me was the diverse community that came together. We were a group of 15 individuals that spanned many time zones and came to the workshop with vastly different backgrounds, yet we shared a common goal of designing lives we truly desired.

The workshop – which spanned 4 weeks – provided us with a comprehensive workbook and various frameworks that allowed for deep introspection. In between live sessions we had the opportunity to journal, answer prompts and reflect in ways that made each subsequent session more meaningful.  Over the course of the month, I had numerous “a-ha” moments that have really shaped my thinking. Some key learnings that resonated with me included:

  • My definition of success is not fixed; it evolves over time, AND that’s perfectly okay.
  • Life is not about achieving predefined milestones; it’s about embracing the journey and choosing the path that provides the greatest coherence and aligns with our values.
  • There is no singular life or path for me; I have the power to choose and shape my next chapter. How exciting is that?!

The mix of large and small group breakout sessions was a highlight of the workshop. These sessions fostered a sense of community and allowed us to share our stories authentically. I felt comfortable sharing my own journey and receiving valuable feedback and ideas from others.

The frameworks introduced in the workshop were not just theoretical; they were practical tools that I could carry forward into my life. Concepts like Work view/Life view/Cohesion and Balancing Work, Play, Love, and Health provided me with a new lens through which to view my life. Problem-Framing allowed me to break down the complex questions I kept asking myself into actionable steps, while Odyssey Planning opened my eyes to multiple potential paths for my future.

Perhaps my favorite phase of the workshop was the Prototyping exercises we did. I had the opportunity to turn my inner reflections into tangible action plans. I defined prototyping questions for two career paths I wanted to explore: ‘the work and lifestyle of a franchisee’ and ‘starting my own business’. The breakout groups provided a space for radical collaboration, where I received fresh ideas and perspectives for moving forward that I hadn’t considered before.

As the workshop concluded, I found myself energized and equipped with newfound clarity. But my journey didn’t end there. Our workshop community was so strong that many of us decided to continue our connection through a Mastermind group. This group serves as a support system, where we meet monthly to keep each other accountable and collaborate on our life design.

I also took my ideas, odyssey plans, and prototype boards to my personal stakeholders – my spouse and friends – for additional ideation. I am now running multiple action plans against multiple potential lives, embracing small steps and forward momentum.

I am filled with excitement for what the future holds. This life design journey has been transformative for me. Through the DYL workshop, I gained not just insights but a renewed sense of purpose. As I continue to apply these principles to my life, I am confident that I am on a path that aligns with my values and aspirations. Mine is a continuous journey of self-discovery and intentional living, and I can’t wait to see what’s next!


Kristen Donnino lives in New York City with her husband and two daughters. She spent the last 18 years leading Product and Design teams at early-stage tech startups and is actively designing the next chapter of her life! She loves reading, traveling, spending time outdoors doing just about anything (hiking, skiing and gardening with family are faves) and has recently started oil painting again.