Welcome to the third and final part of my series on how to begin personal projects with intention. Today, we close out the series by learning techniques for finding direction and brainstorming project ideas.
Living in greyscale
A few years ago,1 I realized that I was quite discontent in my life. The morning it dawned on me was a pretty normal day. I was sitting on the floor by my bedroom window, nursing a mug of coffee as I looked out at the street below. I often started my mornings this way before jumping into remote work.
From my window perch, I watched various inhabitants of San Francisco going about their morning. Energetic joggers breezed by, couples ambled with their sniffing dogs, and groggy tech workers hunted down their first caffeine of the day. I daydreamed about their lives as they passed by—what they were doing that morning, what their dreams were, who they were friends with.
But as I sat there cross-legged tracing these invisible threads, I started to feel a sense of unease. I noticed that I could not romanticize my life in the same way. And as suddenly as a car horn blaring from the street below, I realized I had no idea what I was doing with my life.
Moments of dissatisfaction tell us something
I don’t really know why these “aha” moments can sneak up on us—or how we can live within a grayscale monotony for months without consciously realizing.
Maybe at the time, it was because my life was pretty good.
I liked my job well enough, I had close friends, a beautiful apartment, and a loving boyfriend. On paper things looked great. I had so much to be grateful for, and I felt a sense of shame for recognizing that I felt quite empty.
But regardless of my circumstances, there was no denying that I felt completely and utterly disconnected from myself.
Despite how tough they can feel, moments like these are blessings in our lives. They act as inflection points, which offer insights if we take the time to explore the root of our feelings.
If we are dulled and dissatisfied, this is a signal that something needs to change. We can reevaluate our priorities, kick-off new projects, and work on the areas of our lives that need attention.
The key is in correctly identifying the root of the problem. We need to know what’s missing so that we can discover what to change.
Method to my madness
My method for finding direction and generating ideas is what I like to call Whiteboard Mapping. It’s a practice I’ve developed over the past decade, and it’s changed the way I think about important decisions, especially in these moments of inflection.
The idea is simple: using organization as a tool to elicit self-awareness. (I’m convinced I left the womb with sticky notes and dry-erase markers clutched in my little baby hands.) My framework focuses on identifying where we are now, where we want to be, and ideas for how to get there. Pairing this with a regular mindfulness practice can be transformative—if you’re curious, I’ve written more about that here.
The exercises below can be done in a journal if preferred, but I strongly recommend trying out the whiteboard first.2 Whiteboards are awesome because they also act as visual tools that we can see and interact with throughout the day. Ideas don’t always come all at once—they take digestion and thought. With a whiteboard, our ideas are not stored in a journal that we have to return to and open throughout the day; they’re right in front of us, which makes brainstorming a more fluid process.
Whiteboard Mapping
Where am I?
Before we can figure out what to work on, we must get a sense of our bearings. We have to find ourselves on the map so that we can chart a course for where we want to go.
The easiest way of doing this is by assigning levels of satisfaction to different aspects of our lives. It’s up to you which pieces to reflect on, but I recommend starting out with:
Health
Community & Love
Work & Finances
Creativity & Hobbies
It’s important to understand how we feel about the various areas of our lives, so that we know what to prioritize when we get to the project planning phase.
Exercise 1: Assessing Our Lives
Create a list (like the one above) of the important aspects of your life.
Assign a satisfaction level to each area.
Answer the following questions for each area
What do I enjoy about where I’m currently at?
What do I dislike?
Is this area of my life affecting my broader feelings of dissatisfaction?
Do I want to prioritize improving this area of my life?
In addition to recognizing where we are now, it can be useful to identify where we’ve been and the things we enjoyed and disliked about our previous experiences.
Exercise 2: Assessing Our Past Projects
Identify 3 past projects and answer the following questions.
What aspects of this project did I like (working with people, type of tasks, etc.)?
What aspects of this project did I dislike?
What would I like to do more of?
Where do I want to be?
Next it’s time to ideate where we want to be. Exercises 1 and 2 help us to identify where in our lives we feel dissatisfied, and now we can brainstorm solutions.
This portion of Whiteboard Mapping can be as idealistic as working to achieve a life-long dream of ours, or as simple as increasing our exercise consistency. We should write out whatever comes to our mind, and we’ll be able to prioritize how we want to spend our time in the next section.
We shouldn’t be in a discerning phase yet—this next exercise is all about idea generation so that we have lots of options to choose from.
Exercise 3: Mind Mapping
Pick a handful of problem areas that were discovered in Exercise 1.
For each one, list five words or ideas that are related to a solution to that problem area. Incorporate learnings from Exercise 2.
When an idea feels good, circle it. Bonus points if an idea can solve problems in multiple areas of your life.
Organize ideas and rank them
Now that we have lots of ideas to work with, it’s time to prioritize them and ultimately pick a project to work on.
This part should feel exciting. We have lots of options to choose from, and it’s just a matter of whittling down to the best ones.
Exercise 4: Prioritizing Our Ideas
For each circled idea from Exercise 3, answer the following questions.
What problem areas does this idea/project solve?
Why do I care about the outcome of this idea/project?
Are there any setbacks or tradeoffs to consider?
Are my goals rooted in fear or external expectations/pressures (i.e.: social pressure, financial pressure, etc.)?
Identify the top two ideas.
Based on how you feel and how your ideas meet your problem areas, pick an option!
How this has worked for me
Back when I was having my existential crisis, Whiteboard Mapping helped me to realize that I was lacking a creative outlet in my life. I sensed that reconnecting with my creative side would bring me fulfillment and lead me to deeper discoveries. I also wanted to start small so that my new project felt doable to incorporate into my life.
After deliberating between a few different artsy projects to start, I decided on learning how to watercolor. I walked to the neighborhood arts and craft store, bought a small paint kit, a book on techniques, and sheets of watercolor paper. For the next few months, I started watercoloring during my lunch breaks.
This new creative project transformed my mental health and brought me back to an abundant mindset, where I could continue to deliberate (and romanticize) about the other areas of my life.
One step at a time
I want to be clear that we may not have all the answers at the end of a Whiteboard Mapping exercise. Sometimes making our best guess—and trying and learning—is what it takes to know whether we like something or not. Regardless of the results, our efforts will add new layers to our understanding of ourselves.
It’s also important to let go of the notion that there’s a single, perfect path we need to uncover. Fulfillment doesn’t hinge on one ideal pursuit. There are countless ways to live a meaningful and enriching life, which is beautiful and liberating.
By approaching this process with curiosity, we create space for discovery and growth. So without further ado, grab your dry erase markers and start ideating!
Thanks so much for reading!! -Ari
Long before streaming
If you’re wondering whether my friends make fun of me for the several whiteboards I own, the answer would be yes.
Thank you so much for sharing this, Ari! I've definitely experienced moments of dissatisfaction and uncertainty, and I love how you break down the process of identifying what truly matters and finding direction. It's a great reminder that reflection leads to clarity and clarity opens up creativity!
This technique helps more than we might be willing to admit.
Too many people are unhappy, but when you ask them what to they want - they can't seem to provide the specific picture of their life.
You need direction if you want your car to take you somewhere.