Waiting Decades to Finally Follow Your Dreams
A lifelong deferred dream, a sacrifice worth the wait [The Other Side of Enough: Interview #5]
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The Way of Work explores stories of where we fit in the world of work. This is part of the new series, The Other Side of Enough, exploring what life is like when you have enough to never work again.
What if the things that bring us the deepest meaning don’t make any money?
The popular mantra of “follow your passion” is often endorsed by people whose passions conveniently happen to be well-timed and highly marketable business opportunities.
But what if your purpose doesn't pay?
For many of us, life’s day-to-day demands take precedence – earning a living, raising a family, and fulfilling obligations – leaving little room for other ambitions. Purpose can feel like a luxury that’s squeezed out by the pressures of a busy adult life.
In our last interview, Omar wrestled with finding intrinsic motivation after achieving enough. This week’s story is different. Sara Pendergast always knew what she wanted to do: become an artist. But she was also pragmatic, having no delusions that her passion would somehow manifest into a profitable career.
So Sara did what she needed to… she put her passion on pause. It was a pause that required extreme patience, lasting over 30 years.
Instead she channels her energy into a long career as a business owner and consultant. But when she and her husband reach “enough,” she doesn’t hesitate to dive into the dream that she deferred for so many years, with a focus and intensity that rivals her previous career.
Sara’s journey reveals the patience and sacrifice it takes to pursue a creative craft seriously. She shows what it means to engage with the world on a deeper, more resonant frequency—one that transcends the surface-level hum of daily obligations. It’s an example of the richness and meaning that come from dedicating yourself to a craft—not as a hobby, but as a way of truly seeing, feeling, and connecting with the world. And it’s a reminder that some passions really are worth waiting for.
Building Toward a Dream
“Being an artist was an absolute, lifelong dream. I've been chomping at the bit to do this my whole life.”
Sara’s dream started early. She grew up immersed in art, with a father who nurtured her passion from the beginning.
“My father was an amateur artist. So we grew up appreciating art and going to art museums. He would paint and he would draw. His best friend was a professional artist (who worked the nightshift as a janitor of the local cinema).”
But even as a child, Sara saw the hard truth behind the beauty.
“I thought: wow! That looks really good. But it also looks like you don't really make a lot of money, not enough to raise kids the way I wanted to.”
By the time she was considering college, she’d already understood the trade-offs.
“I looked into art college, but that path, once you're done, didn't look like I'd get the life that I really wanted, nor be able to have a family the way I really wanted.”
It wasn’t an easy realization, but rather than force a dream that felt financially impossible, Sara embraced a pragmatic mindset. She drew inspiration from the women in her life who modeled resilience and pursued their passions later in life.
“The women in my life sacrificed early and then did things later. [For example,] my mother went back and got her PhD when she was 50, then became a professor. And so I just thought that was a normal pattern.”
Sara focused on a more practical question: what could she do early in life that would build a foundation for what she wanted later?
“I created my career based on: what skills do I have? How can I make the most money possible? I didn't really care what it was, because I had an end goal in mind. So I did that.”
The Practical Years
After college, Sara decided that starting a business was the best path forward. She and her husband,
, co-founded a book packaging company. Sara’s work revolved around organizing and presenting complex ideas through words—communicating knowledge in ways that could inform and influence others.“For 19 years, we created social sciences and humanities reference books.
But Wikipedia and the Internet changed the way people consumed information, especially reference book information.”
This firsthand experience of disruption sparked a new curiosity in Sara: how people and organizations adapt to change.
“I became really interested in the digital transformations that companies were going through; in how businesses get people to do things differently. [So I] made a consultancy around that.
I [became] an expert in organizational transformation. The human dynamics fascinated me.”
Meanwhile, Sara fit in art where she could, sprinkling it in here-and-there, but never with enough time or commitment to satisfy her bigger aspirations.
“I would spend the odd Saturday where I got to paint for 4 hours. But then it was right back into not painting at all. So it was really sporadic.”
Then came the pandemic—a forced pause that made Sara and her husband confront their assumptions about happiness and enough. With most financial obligations behind them, they realized they could trade stress for simplicity, creating space for her long-held dreams.
“Suddenly, we were living on way less. And we thought, this actually feels better.
The things that we had become habituated to no longer felt important. We figured out how to spend money on what made us happy, not on stuff like clothes and eating out, that we used to compensate for the stress and frustrations of working.
And Tom and I drew up a 40-year plan and went: ‘Well, we think we have enough.’”
Reaching “enough” granted Sara that freedom to fulfill a dream long deferred: to finally become an artist.
The Artist’s Journey
“I stopped working and spent an entire year painting every day.”
Not long after starting, Sara realized art isn’t just a hobby, a fun way to spend her time. It was something much deeper. A new way of communicating, one that spoke to a part of her that words alone never could.
“I realized that I'm really intrigued with visual language.
A big part of my life was language as a way to persuade people to do something different. Language as a way to transmit knowledge to all sorts of different audiences. All through words.
And yet, in my experience, so much of life is experienced with a visual connection. So I really wanted to explore: How is painting or drawing a visual language? How is art something that connects you to others?”
In hindsight, her prior careers were breadcrumbs of a deeper curiosity around communication and connection with others and even herself. This interest propelled her daily painting sessions into something far more serious: a pursuit of mastery in visual communication.
“After a year of doing it on my own, I was convinced that this was a path I wanted to explore. But I also felt like I couldn’t make my paintings look like the picture in my head.
To create the kind of art I valued, I needed to develop a deep level of expertise. I realized I could spend a lifetime honing my skills as an artist ... and that would be a life worth living.”
Sara then started an apprenticeship under Jeff Hein, a master artist who pushed her skills to new levels. Jeff would tell her she was "trying to write poetry with a very limited vocabulary.” In her prior life, Sara was the expert, the one giving feedback and guiding others through complex problems. Now, she had to embrace the discomfort of being a beginner again, requiring a willingness to start from the basics. A shift that was both challenging and humbling.
Today, her daily artistic routine looks more than just a casual activity, it’s a commitment.
“I really just get up in the morning and I go to work. And I work all day long. And Tom interrupts me for lunch and dinner. And then we spend time together in the evenings. But I spend time at this like it's a job, because it requires so much of me.
This is something I want to give my attention to. I find it endlessly interesting to try to create an image that resonates with me.”
This pursuit of mastery over her craft gives her a clarity of purpose to her life.
“I have a very specific idea in mind of what I'm trying to get to. I feel like if I don't develop these skills and start producing art that resonates with me, I will not have lived the life that I want to live.”
From Extrinsic to Intrinsic Value
Why does she do it? And how does the motivation contrast to her prior work?
“This is for me. I'm not trying to please a client. I'm not trying to hit somebody else's expectation for what they want.
It's all internally driven, based on my own interests. Whereas I'd say that my interest before was in making as much money as possible. I didn't really care what I was doing.”
But she can’t help but notice that she’s transitioned away from something that society valued, to something more ambiguous to the outside world.
“I realized that in stepping into an art world I was stepping into a pursuit that not very many people understood, and certainly not very many people valued.
I actually think American culture in general doesn't value art. But I feel like it's a central part of the human experience.”
She recalls talking to someone very “business oriented, runs his own companies, and is very successful.” She told him about becoming an artist, but she got this response back:
“‘That'll be a lot less challenging.’
And I just thought, ‘well, actually, it's a lot more challenging!’
[Art] is a much deeper and more complicated subject than I even imagined. I really didn't know what I was getting myself into. I didn't realize how much there was to it.
I still really want to do it. And if people don't understand… they don't understand.”
This begs the question: after living a life where our “value” is so clearly defined, what happens when we move onto something less clear?
“How do we value ourselves now that we don't need value from the market? Because that's the only value we've ever really experienced.
I don't think that the hard work that goes into art is valued at all.
So the best I've come up with is if, first, I create a picture that resonates with me. Then, if other people see it and it resonates with them. And on top of that, if they are willing to pay for it. They want to take it home and have it with them. That would be the trifecta.”
In Pursuit of Meaning
Art may not be your thing. But maybe there’s another pursuit or craft lingering from your past that you’ve put on hold, letting other obligations take priority. Something you always wanted to do, but never could find a way to fit it in. Or it never seemed, well, all that practical.
Like Sara, it may require you to wait decades before you’re ready to take on that pursuit. It may require you to start from scratch, dedicating years, perhaps the remainder of your lifetime, to developing that craft. It may even require you to defy cultural norms and let go of others’ expectations of you.
“Unlike the hollow expertise I developed during my corporate career, the mastery I pursue now feels very rich and rewarding. It helps me explore why I exist at all and allows me to connect to others in ways that feel very natural.
What is it in life that means something to me? What catches my eye? Why do I think about what I think about? All of these things I can't describe, but I might be able to create a visual language for showing what they are and what they mean to me.”
I want to end with one particular story Sara shared to illustrate the depth of connection she has found through her art.
“I have a painting of a little girl (shown above). She was at this party just running around, being the cute little kid in the group. And her ponytail was catching the light in a way that was fascinating to me because she had impossibly thin hair. And I just thought, ‘this is such an interesting ponytail. I really wanna try to get that.’
She was also so vulnerable and uncertain. She was napping, and all these people showed up at her house. When she woke up, she sat in her dad's lap, and was taking in the scene of all these people she'd never met.
And so I thought about the vulnerable look on her face and the way the light made her ponytail look, and thought, ‘Well, how can I get that?’
I took, I don't know, a bazillion photos of her. I was able to take enough that I could create a drawing.
But my painting of her looks, in my mind, much better and more representative than any of the photographs that I took.
I didn't want to keep any of the photographs. But that drawing. Yeah, that resonates with me.”
Sara’s story isn’t just about art—it’s about choosing to redefine what makes life meaningful, even if it must wait. Her patience, persistence, and pursuit of mastery remind us that the best things in life don’t always pay, but are still worth pursuing.
The art featured within the sections are all original works by Sara Pendergast (excluding the title image). To learn more about Sara’s work, visit: sarapendergast.com
Special thank you to from for introducing his wife to me for this project. He has a new piece about his and Sara’s pursuit of purpose that you should check out. This interview was transcribed, then summarized and edited for clarity.
If you’ve enjoyed The Way of Work, you can support the project by commenting, hitting the ❤️ or 🔄 below and/or sharing it with a friend.
Bonus Questions
What are resources that have helped you in your transition?
Mastery, by Robert Greene
Art and Fear: Observations on the Perils (and Rewards) of Artmaking, by David Bayles and Ted Orland
Before & After - on a scale of 1-10 (10 being best), how would you rate the following before and after enough:
Health: 8 → 9 (+10%)
Stress (10 is low stress): 3 → 9 (+60%)
Creativity: 6 → 10 (+40%)
Relationships: 9 → 10 (+10%)
Impact: 6 → 6 (0%)
Meaning: 7 → 10 (+30%)
Work Hours/Week: 60 → 40 (-33%)
This is part of the series, The Other Side of Enough, exploring what life is like when you have enough to never work again. Check out the next part:
Great interview, my favorite line: “Unlike the hollow expertise I developed during my corporate career, the mastery I pursue now feels very rich and rewarding."
Another fascinating story about an amazing lady! No doubt Sara is a talented and hardworking artist. I actually agree that you need have bread first before you pursuit your passion which may not bring bread. I admire Sara's pragmatic approach to her life and admire her more that she didn't give up her passion and true love after 30 years. There is a Chinese proverb "money is not everything, but without money, nothing can be done".
Sara's story will inspire a lot of people to look into our heart what we really love in our life. Her paintings are extradentary and I am sure there are people like to purchase her art work.
Now I am wondering if Rick's passion is writing because you really write well.