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Flirting With Our Possible Selves

Updated: Jun 11

I first came across this idea of flirting with possible selves, while reading Range, by David Epstein. The story of Frances Hesselbein, former CEO of the Girls Scouts of USA and founder of the Frances Hesselbein Leadership Forum, is a fascinating example of someone who trusted the process and let herself guided by life's surprising experiences. When the author asked Hesselbein what training had prepared her for leadership, she replied that "she just did whatever seemed like it would teach her something and allow her to be of service at each moment." As diverse experiences accumulated, they transformed her into a leader, before she even realized or could think of herself in that role. Leadership turned to be an attitude and a way of acting, rather than a formal title or an external recognition.

Lately, I thought a lot about the idea of imagining different future scenarios and prototyping different versions of myself. I sometimes draw this imaginary tree where every branch is a different path that could have shaped, every time I took a different decision in the past. I imagine that in 2000, when I was admitted to the university in Cluj, I would have not accepted the offer, and went to Bucharest instead, like my initial plan was. How would my life be now? Or instead of deciding to live and study in France on a very small scholarship, I would have just looked for another job and stayed where I was. Or instead of accepting a job in Belgium, I would have decided to not leave my country, family and friends. It's a fun exercise, but it's also scary. Because it proves how uncertain the future is and how one decision can shape an entirely different life context.

A few months ago, a friend of mine recommended me this book called Designing Your Life, by Bill Burnett and Dave Evans. The core idea is that a well-designed life is a life that is constantly creative, productive, evolving, and often, full of surprise. While the ideas were not new to me, I liked this framework borrowed from the world of design thinking.

There are eight main steps in the Designing Your Life (DYL) discovery process and while it sounds easy, it takes a few weeks or months of journaling and trying things out. We need to use our brains and think about what happened in the past, so we can learn and avoid the same mistakes in the future.

But when we want to grow and broaden our experiences, acting must come before thinking. As Herminia Ibarra, Organizational Behavior Professor at London Business School puts it:

“We learn who we are just by living, and not before.”

We need to experience, expand our network and then re-adjust our personal narratives. Introspection alone is not enough. A quiz and a course that will magically reveal our talents and ideal career, will not help us find our dream work. Themes emerge while we are doing stuff, and we always need to start from where we are now.

1. Find the Problem

When we feel that something is not quite right and balanced in our lives, we often jump into problem solving mode. We fall into the trap of the easy fix and we try to find the fastest answer to life, the universe and everything. How can we feel happier? There must be an easy way that we just didn’t figure out yet.

A whole industry of lifestyle gurus is feeding on our need for certainty and having answers for how our future will look like.

But what if we try to fix the wrong problem? Problem finding is just as important as problem solving. Sometimes we try to find solutions to the wrong problems. We might want to become faster and more efficient at climbing a ladder, but if the ladder is leaning against the wrong wall, we get to the top and we ask, “what am I doing here?”

People who are unhappy in their current jobs or relationships, find it sometimes easier to leave than understand the root cause of the problem they’re facing. And what if the problem was never the boss, the culture, the partner, or the colleagues? What if the problem was their perception and all they needed to do was to look at it from a different angle?

We all know someone who always complains that others don’t care about them and they feel left out and not important. Nobody told me. Nobody asked for my opinion. I was not involved. But when you ask them what they proactively did to get involved, often the answer is nothing. When you try to find the problem, look for patterns and talk to a couple of people you trust, to get an outsider’s opinion. Sometimes, half of the problem is solved when you just explain it to someone else.

The first thing we need to understand about a problem is whether it is actionable.

We might be unhappy that we work in an open space, and there is too much distraction. But the company we work for always had open spaces in all its locations and that situation will not change any time soon. That’s not a real problem; it’s the reality. And we cannot fight reality. We should have probably not started there in the first place, if working in an open space is such a big issue for us. Or we can reframe how we look at an open space and start using some techniques to avoid distractions, like focus music or background noise cancelling headphones. There might also be some positives in being able to connect more to your co-workers and work on collaborative projects while being in the office.

When we are trying to solve a problem, we must start with what we know about the problem. We start with the data, with the facts, and we try to avoid building stories of self-justification.

2. Assess where you are

If you want to explore where you’re going, you need to know where you are. There are many existing frameworks to assess where we are in each area of life. The Designing your Life framework looks at four main areas of life: Work, Play, Love and Health and proposes a visual dashboard that we can use throughout the process for regular assessments.

© Bill Burnett, Dave Evans, Designing Your Life

When we think about work, we should think broad and include all the different types of work we do and not just our job. My main work is being a marketing manager, but I also run activities in a women’s organization, I help other people grow and become more driven, I work at home on different household activities and personal projects, I write and so on.

Work is anything that is productive, whether you have a financial compensation related to it, or not. Think about your work as something you do, and not someone you are.

Play on the other hand, is related to any activity we do for the pure enjoyment of it. There is no expectation of outcome in play. It can include organized activity or productive endeavors, but only if they are done for the joy of it. For example, I might include cooking as play, when I am experimenting with a new recipe for the fun of it and I don’t mind if it doesn’t turn out the way I expect. But when I cook dinner during the week, I see it more as a functional activity than a creative one and therefore I consider it work.

Love includes all your different relationships that bring you positive energy, affection, and appreciation for. So, it’s not only about romantic love, but also extended family, friends and community members.

And finally, health is measuring your general physical and mental well-being. How do you feel on most days when it comes to physical comfort, energy level, mental focus, and drive? Do you take care enough of your body, do you exercise and intentionally practice activities that clear your head? It can be sports, walking, hiking, anything that keeps you fit, active and in a good state of health.

So, how does your dashboard look like? Is the tank full in each area?

3. Building a compass

When we think about the future, it’s better to embrace the mindset of an explorer who is guided by a compass rather than a treasure hunter, following a clear map of the treasure chest. Nobody can clearly predict what the future holds and what changes will occur in our lives. Hopefully, the last two years taught us some good life lessons in this sense, so we are better prepared for the future.

A compass should be built around two areas: our Lifeview, which includes our ideas about the world, what we value, what’s important for us and gives us meaning. And the Workview, including all the different areas of work that we do, that we like and want to further master. The goal of this exercise is to see whether our Lifeview and Workview are coherent.

A coherent life can clearly connect the dots between three things: who we are, what we believe and what we are doing.

If one of my core values is health and I am an active person who takes care of herself in all areas, but I work for a company that makes cigarettes, I have a lack of coherency between my Lifeview and Workview that can cause misalignment. Or if one of my values is supporting others and collaborating, but I work in a culture that encourages radical competition, praises individual achievement, and discourages collaboration, I will have a hard time finding meaning and feeling any joy.

There are times when we need to make conscious compromises. For example, if in my Lifeview poetry is the most important thing that the world needs, I write poems every day, but at the same time I know I cannot earn a living from poetry and I have two small children I need to provide for, I might take a conscious decision to have a job that will help me support my family. It’s not completely aligned with my Lifeview, but I am aware of that and for the moment it’s the best decision. In time, I might work my way into finding more coherence between the two areas and find a way to earn my living from poetry.

4. Wayfinding: Engagement and Energy

When we have a demanding job, an active family and social life, we might find ourselves on a Friday afternoon thinking “where did this week go?” Do we feel we had control over the way the week unfolded? Were we in the driver’s seat or someone else made the planning for us? How do we spend our days and how aware are we about which daily activities engage us and which not, what gives us energy and what drains our batteries?

I wrote about how we spend our time and engagement before, but the Designing Your Life framework proposes a practical exercise called Good Time Journal. You can download the template here. Like with measuring flow experiences, you need to set up reminders every two hours, and then enter a log regarding the activity you are doing at that moment, or something you did in the previous two hours. Then assess the level of engagement and energy you feel. After a couple of weeks, you will start seeing some patterns. (Spoiler alert, meetings are usually the biggest energy vampire for most people. If that’s not you, please reach out, I would love to learn your secret.)

“To live means to experience—through doing, feeling, thinking. Experience takes place in time, so time is the ultimate scarce resource we have. Over the years, the content of experience will determine the quality of life. Therefore, one of the most essential decisions any of us can make is about how one’s time is allocated or invested.” (Mihaly Csikszentmihalyi)

5. Getting Unstuck

The best advice when it comes to generating new ideas is go for quantity and forget about quality. After assessing which activities keep you engaged and energized, think about how much time you currently spend doing those activities. In the end, if we want to feel happier in our daily lives, it’s all about obtaining and maintaining a baseline of well-being and not just having peak moments of happiness and joy a few times a week. One way of doing this exercise is to draw a mind map of all the activities you like doing and which give you good vibes and energy.

Set you timer to 25 minutes and start writing your mind map like in this example. Go for quantity!

© Bill Burnett, Dave Evans, Designing Your Life

After spending less than one hour focusing on what you like to do and exploring some further connections, you will be inspired to see many ideas that didn’t come to surface before.

6. Build your “Odyssey Plans”

When you explore doing different things, changing jobs and career paths to do more meaningful work, the worst you can do is jump to a new thing too soon. In my late twenties I suddenly became very fond of baking and dessert making. Because I was not happy with my job back then, a crazy idea started to shape: what if I would do something completely different and work in a totally different industry? As I was preparing to leave for half a year to study in France, I thought, this might be a good launch opportunity into a future food service career. I was already imagining my future food service business, painting how the place would look like.

So, I enrolled in a four-month program, to obtain my pastry certification that would make my dream possible. The training also required 120 hours of mandatory apprenticeship, and I found a shop who accepted that I would work only during the weekends, next to my full-time job. For three months, I spent my Saturdays and Sundays getting up at 5am and working in a pastry shop until 2PM. I did everything, from preparing ingredients, running back and forth to the walking fridge to bring frozen cakes for decoration, baking tart shells for seven hours in a row until I could not feel my back, kneading one thousand sandwich breads, baking hundreds of trays of pretzels and decorating vanilla cupcakes with pink buttercream frosting. It was the hardest work I had ever done. I loved the people and the communal feeling of that place, but I didn’t enjoy the work. My career path in pastry was a definite no go.

When we want to explore different options, the best strategy is to think like a design engineer and create different prototypes that can be tested before launching the first production batch. Write down what work you would enjoy most and then list your strengths and expertise. What are you good at? What is your superpower? Then draw a line and mark a five-year timeline. Start from where you are now and imagine how the new path would look like in year one, two, three, four and five. It will be an evolution. See the example below.

© Bill Burnett, Dave Evans, Designing Your Life

Once you imagined the journey in big lines, think about what resources you need, how much do you like the idea, how confident you are and how coherent is this plan with your Lifeview.

You can repeat this step and have up to three plans, but you can also start testing the first one if you only have one. The whole idea is to not get stuck in planning and just go out and try stuff.

7. Just do it

What always helps me when testing new territories is adopting a beginner’s mind. Start playing around, learn a few new things, test them out and repeat. I just focus on learning and try not to judge myself or compare myself to others.

Comparing ourselves to others is feast for our inner critic whose sole purpose is to block us. Instead, what always works is going out and talking to people.

Talk to people about what you are exploring and see if it still makes sense after you heard yourself talking a few times about it. Talk to people who already do what you want to do. Talk to people and ask questions that can help you clarify your thoughts. Just talk to people. Don’t lock yourself in an ivory tower with your idea and expect that everything will just turn out fine. Ideas need to be out in the world, to be seen and grow. We need other people if we want to grow our ideas. We cannot achieve anything great without the support of others.

The idea of prototyping different versions of ourselves is strongly related to play and having more play in our lives helps us reconnect with our intuition and creative energy.

Most of us are overusing our left brain and when we forget to play, we risk overthinking and over planning, which is not very fun. Plus, we risk burning out. Experimenting and having some side gigs that might or might not turn into something serious at some point, is a sort of play that can add a ripple effect in everything else we do.

Throughout the ages, people have been asking the same questions: Why am I here? What am I doing? Why does it matter? What is my purpose? What’s the point of it all? The only way to find the answer is to try different things. The dark horses, the fulfilled people that Ogas and Rose study, do pursue a long-term goal, but they only formulate it after a period of discovery.

Self-awareness comes from expanding our perspective and getting more experiences. Just by doing and prototyping different experiences, we can learn what we like and what we want more of.

The best strategy is to act our way into discovery and not wait for the answer before doing anything.

After going through the DYL exercises, I realized that without being aware of it, I have always been prototyping and experimenting. And this is what helped me move forward. I always had a main job, while experimenting with other secondary activities that I saw more like play, so the stakes were lower, and the fear of failure minimized. That helped me develop new skills and opened new doors. Later in the journey, I incorporated those skills in what I was doing as main job, which in turn, created a new range of experiences and opportunities.

But in a nutshell, it’s all about three words that someone was smart enough to trademark: Just do it.

8. Commit or let go

Have you ever heard about “The Jam Experiment”? In 2000, psychologists Sheena Iyengar and Mark Lepper ran a supermarket experiment. In one instance, they installed a tasting table showcasing 6 different types of jams. 40% of shoppers stopped, they sampled on average 2 different types of jams and 30% of them bought jam. In the second instance, the researchers showcased 24 different types of jams. 60% of shoppers stopped, they sampled 2 different types of jams, but only 3% of them bought jam. This experiment has been used to illustrate the paradox of choice. The more choices we have, the more difficult it is to choose.

So, when we think about our future options, it’s better to stick to a small number of scenarios and then commit to one. It doesn’t mean that this commitment is for life. But we need to spend enough time on one option, in order the deepen our understanding of it and get to a more profound level of experience. If I am envisioning a new career in photography, I will want to spend at least a few months or even a year, playing with photography as a side gig, and immersing myself in the world of photography where I can meet like minded people.

Next to deepening the learning and mastering the skill, being part of a tribe is equally important for getting a sense of acknowledgement and feeling motivated to continue.

Give up too soon and you will find yourself jumping from one shallow experience to the other. Soon, you will feel stuck in the paradox of choice. Stay too long on the wrong path and you will later regret wasting precious time that could have been spent on a more fulfilling activity.

Finding this balance is not exact science. It’s an art. And like in any artistic endeavor, there is uncertainty and risk of failure. It can get scary. But that’s where our instinct and intuition come to play.

One of my guiding principles that I apply in everything I do is the Goldilocks principle. If something doesn’t feel right, I first try to understand the possible cause, and then I change something until it does. Anything that is not in the right amount, can cause discomfort so it needs attention and probably change. But when we adopt a more playful attitude, we have the power to turn what scares us into something fun.

Look back at your journey for the last ten years. How many of the things you did were part of a clear plan and how many were opportunities that came up along the way? Did your journey follow a precise map, or it was a journey guided by a compass, with different opportunities that you took along the way and that connected at some point? Or maybe you had no map and no compass, but you still got where you are today.

Now try to imagine your next ten years. How many roads do you see from where you stand now? What do you see on the side of the road? Who else is travelling with you? Who do you want to meet on the road and what stops do you want to make? What do you need to carry in your backpack?

As we all experienced at some point in life, we need to carry a lot less than we think, to have a memorable and pleasant journey. All that matters at the end is who we were with and how we felt. If we apply this to our work and everything we do, we might get more satisfaction from the activity itself than the result and goal we dream of. The end is a peak that we often remember most vividly, but it’s short lived. The journey is the hardest and the longest part, and we might want to make it more fun and enjoy the ride. We can have a compass, a toolbox and some good guiding principles that help us take less bad decisions, but we can never control luck and we have no crystal ball that can predict our future.

It’s tempting to analyze our decisions in hindsight, and believe we can predict the future, but if we want more peace of mind, we should accept that we can never obtain complete certainty over our future. We can experiment with different scenarios and take the right decisions in that direction, but it’s not a guarantee.

But what we can do at any time and point in life, is to clarify our values and purpose, and just do more of the things that keep us engaged and happy.

We should put less importance on finding happiness and just experience happiness every day. When we obsess about finding happiness, we forget to enjoy those moments that are right in front of us. So, let’s have more fun, let’s play more, let’s learn new things every day and let’s judge less. The key to happiness is not to build plans for a predictable future, but to embrace the uncertainty that comes with discovering new wonders every day.

Recommended Resources:


Designing Your Life [BOOK], by Bill Burnett and Dave Evans

Dark Horse: Achieving Success Through the Pursuit of Fullfilment [BOOK], by Todd Rose, Ogi Ogas

More Isn't Always Better [ARTICLE], by Barry Schwartz,

What Kind of Parent Are You, Carpenter or Gardener? [ARTICLE],

A Playful Way to Problem Solve [ARTICLE], by Ingrid Fetell Lee


What Frogs in Hot Water Can Teach Us About Re-thinking [TED Talk], Adam Grant

The Surprising Science of Happiness [TED Talk], by Dan Gilbert

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