Do people look at your life from the outside and think you’re really successful? Maybe you have a leadership role at work or run your own company, but inside, you feel like something is missing.
Where does that sense of disconnect come from, and how can you find the fulfillment you crave?
I was fulfilled… until I wasn’t
I used to make a full-time living from a board game website I founded. It gave me time and location freedom, and I earned more money doing it than in my corporate job. Yet, despite checking all the “success” boxes, I still felt unfulfilled.
And worse, I felt guilty for feeling that way. I knew that, in many people’s eyes, I had everything they could want – so why wasn’t it enough?
I tried various ways to make myself feel more grateful for what I had, to appreciate my success more. But it still wasn’t enough.
I needed to understand why I felt this way and what was missing.
If you’ve ever felt this disconnect, I want to share with you the four things that helped me the most so that you can uncover what fulfillment truly means for you.
The Social Science Behind Why Success Feels Empty
To understand why success and fulfillment are so often tangled together, I turned to social science. One concept stood out: social contagion.
Social contagion
Have you ever been at a party where everyone is indulging in dessert, so you do too – even if you weren’t planning to? That’s social contagion in action: the spread of behaviors, attitudes, and emotions from one group member to another.
But this phenomenon doesn’t just influence small decisions like eating dessert – it can shape the entire course of our lives.
Harvard psychologist Susan David explains how social contagion makes us strive for things that others value, even if they’re not what we truly want.
Society tells us that traditional markers of success – like a high-paying job, a big house, or scaling a business – are the ultimate goal. We assume that achieving these things will bring us fulfillment. But if we don’t personally value them, then reaching these milestones can leave us feeling restless and disconnected.
We might be living someone else’s dream – not our own.
No wonder success doesn’t automatically lead to fulfillment.
How to Redefine Success and Find Fulfillment
Once you recognize that conventional success doesn’t necessarily equal fulfillment, the next challenge is figuring out what truly matters to you. This seems like an easy question, but in reality, it’s like asking: What gives my life meaning?
That’s a question philosophers have wrestled with for centuries. I don’t have the ultimate answer to the meaning of life! But I did find some practical ways to uncover what brings me fulfillment.
Susan David in her book Emotional Agility outlines a four-step process to help you identify what truly matters to you:
Step 1: Show Up
Pay attention to what you feel throughout the day and record it. I used a simple notes app to jot down activities I was doing and how I felt while doing them. The challenge was:
- Noticing emotions in the moment instead of ignoring them.
- Resisting the urge to over analyze or judge my reactions.
Step 2: Step Out
Once you have a record of your thoughts and feelings, step back and analyze them objectively. Look at them as data points – patterns to uncover rather than problems to fix.
Face your thoughts and emotions with curiosity and kindness – without judgment.
Step 3: Walk Your Why
This step was the hardest. It required me to break free from conventional success mindsets and creatively redefine my own path.
To do this, I used four different exercises.
1. Values Finder
I searched for a list of 100-200 values (e.g., integrity, freedom, creativity) and narrowed it down to my top five. This helped me see what truly mattered to me.
I also created my own list and guide on how to do this, see my Values Finder Activity.
2. Personal Mission Statement
In The 7 Habits of Highly Effective People by Stephen Covey (Amazon link) suggests writing a personal mission statement
- What do I want to do?
- Who do I want to be?
- What do I want people to say about my life when I’m gone?
3. Past Moments of Fulfillment
I reflected on times in my life when I felt truly proud or satisfied. What values were present in those moments?
4. The Five-Year Reflection
I asked myself
If I continue on my current path, where will I be in five years?
Then, I imagined my ideal five-year future and compared the two.
These exercises made one thing clear: I loved content creation, but I wanted to help people in a more meaningful way than just through board games.
Step 4: Move On
Once you understand what fulfillment looks like for you, the next step is making changes – big or small – to align your life with those values. The tiny tweaks principle is a great way to start.
For example:
- If you value freedom but don’t enjoy your job, see it as a means to an end while you work on a side hustle.
- If you value peace, but stress causes you to overreact, practice pausing and responding calmly.
In my case, small tweaks weren’t enough – I needed a bigger shift.
I explored different ways to modify my business: scaling up my writing team, launching a merch store, even creating my own board game. But none of these ideas aligned with my core value of helping people in a meaningful way.
That realization led me to a pivotal moment: I needed to change paths entirely.
What’s Next?
Now that I understood what I didn’t want, I needed to figure out what I did want. And that was an even harder question to answer.
If you’re on a similar journey of redefining fulfillment, then check out How to Live a Fulfilling Life.
If you found this post helpful, I’d love for you to share your thoughts. What exercises have helped you discover what brings you fulfillment? Drop me an email in the contact form.
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