Quotes don't change your life. You change your life. But sometimes - not always, but sometimes - the right words arrive at the right moment and give you permission to do what you already knew you needed to do. That's what happened to me several times over the past few decades. Here are the quotes that mattered, and why they mattered when they did.
The Permission to Leave
"Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did." Mark Twain wrote that, though there's debate about attribution. Doesn't matter who said it. What matters is that I read it when I was thirty-three, comfortable in a career that was going nowhere interesting, and it hit like a physical blow.
I had everything that was supposed to constitute success. Good salary. Respected company. Clear path to promotion. All my friends and family thought I was doing great. And I was miserable in a way I couldn't quite articulate. Not because the work was bad, but because it wasn't mine. I was executing someone else's vision, building toward someone else's goals, optimizing for metrics I didn't care about.
That Twain quote did two things. First, it reframed the risk. I was thinking about the risk of leaving - what if I fail, what if I'm wrong, what if I can't make it work? The quote made me consider the risk of staying - what if I never try, what if I play it safe forever, what if I reach sixty and realize I spent my best years building something I didn't believe in?
Second, it gave me a timeline. Twenty years from now. That phrase made it real. I could imagine fifty-three-year-old me looking back at this decision. What would he wish I'd done? The answer was obvious. He'd wish I'd taken the shot. Even if I failed, at least I'd have tried. At least I'd have built something that mattered to me.
So I left. Gave notice. Told people I was starting something. Didn't quite know what yet, but knew it had to be mine. That quote didn't give me the idea or the plan or the strategy. It gave me permission to act on what I already wanted. Sometimes that's all you need.
Starting Tallyfy: Words That Guided
When I started Tallyfy, I had clarity about the problem - organizations running on chaos, processes trapped in documents, work happening through endless email chains and Slack messages. What I didn't have was clarity about how hard it would be to build a company around solving it.
The quote that sustained me through the early years: "The secret of getting ahead is getting started. The secret of getting started is breaking your complex overwhelming tasks into small manageable tasks, and starting on the first one." Also Twain, or attributed to him. Doesn't matter. It's true.
Building a software company from scratch is overwhelmingly complex. Product, engineering, sales, marketing, support, legal, finance, hiring, culture, strategy. Everything at once. All of it urgent. It's paralyzing if you let it be. That quote became my operating system. Break it down. Start with the first thing. Then the next. Then the next.
Every time I felt overwhelmed - which was often - I'd come back to that. What's the next smallest step? What can I do right now that moves forward? Not solve everything, just solve the next thing. That's how we built Tallyfy. Not with grand master plans, but with relentless focus on the next right step.
Another quote that shaped how we built the company: "You can't use up creativity. The more you use, the more you have." Maya Angelou said that. I kept it taped to my monitor for years. Tallyfy was born from the insight that work shouldn't be chaotic, that processes should be visible and trackable and improveable. That required believing that you could keep having insights, keep iterating, keep making things better.
In the early days, we'd ship new features constantly. Break things. Fix them. Try again. Some people thought we were moving too fast, changing too much. But I believed what Angelou said - the creativity wouldn't run out. The ideas wouldn't stop coming. Using your creative capacity doesn't deplete it. It builds it.
Failure and the Quotes That Helped
Not everything worked. We built features nobody used. Pursued markets that didn't materialize. Hired wrong. Made strategic mistakes. Spent months on initiatives that went nowhere. That's entrepreneurship. You fail constantly. The question is whether you learn from it and keep going.
"Ever tried. Ever failed. No matter. Try again. Fail again. Fail better." Samuel Beckett wrote that. It became my mantra during the hard periods. Not "failure is not an option" or "failure is the path to success" or any of the other nonsense motivational speakers peddle. Just: Fail better. Learn from the last mistake. Don't make the same one twice. Make new mistakes.
There was a period, three years in, when we almost ran out of money. Not because we weren't growing - we were. But because we'd mismanaged the burn rate, hired too fast, spent on things that didn't matter. We had maybe three months of runway left. I had to lay people off. Had to tell investors we'd screwed up. Had to admit I'd made bad calls.
The quote that got me through that: "What is to give light must endure burning." Viktor Frankl wrote that in different words. The version I know might be a paraphrase, but the truth stands. If you want to build something that matters, you have to endure some burning. The fire isn't optional. It's how you become capable of giving light.
We survived that period. Barely. Cut costs, refocused on core product, rebuilt. The company that emerged was stronger specifically because we'd almost died. We knew what mattered. Knew what didn't. Knew our limits and how to operate within them. The burning had taught us something the success never could have.
When Ambition Becomes Ego
One danger of entrepreneurship is mistaking ego for ambition. Wanting to build something great is ambition. Wanting to be seen as great is ego. They feel similar but point in different directions. Ambition focuses on the work. Ego focuses on the recognition.
The quote that helped me distinguish between them: "It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena." Theodore Roosevelt said that in a longer, better speech. I encountered the excerpt first and then read the full thing.
What resonated wasn't the part about ignoring critics - though that's useful. It was the part about being in the arena. The emphasis on doing. Not talking about doing, not planning to do, not criticizing others for how they're doing it. Actually doing it. That's what matters. That's what ambition looks like. Ego wants the spotlight. Ambition wants the work.
I've tried to build with that distinction in mind. Saying no to speaking opportunities that were about ego. Avoiding startup celebrity culture. Focusing on building a good product and a sustainable company rather than chasing press coverage or funding milestones. Not perfectly - I'm human, ego shows up. But the Roosevelt quote helps me catch it when it does.
The Long Game
Building a software company isn't a sprint. It's a decades-long marathon. You need quotes that remind you to play the long game. The one I return to most: "Rule number one is that you've got to have patience. The market is going to do what the market does. Don't force it." This is from investing, but it applies to building companies. You can't force growth. You can't force product-market fit. You can work consistently toward it, but you can't make it happen on your timeline.
Tallyfy is now over a decade old. We're not a unicorn. We're not going to be. We're a profitable, sustainable, useful company serving thousands of customers. That's success by any reasonable metric. But it took a decade to get here. Not six months or two years or whatever timeline the startup mythology suggests. A decade of consistent work, of learning, of iteration, of patience.
"It does not matter how slowly you go as long as you do not stop." Confucius said that, probably. Point is, momentum matters more than speed. Keep moving. Keep building. Keep learning. Stop comparing yourself to companies that raised fifty million dollars. They're playing a different game. You're playing yours. Stay in your game.
Finding Your Own Wisdom
Here's what I've learned about quotes and guidance and advice: It's all useless until it isn't. You can read a quote a hundred times and it doesn't land. Then one day it does. Not because the quote changed, but because you did. You're finally at the point where you can hear it.
The quotes that shaped my path worked because I was ready for them. Twain's line about regret landed when I was wrestling with that exact choice. Beckett's line about failing better landed when I was in the middle of failure. Frankl's line about burning landed when I was burning. The timing mattered as much as the content.
You can't manufacture that. You can't read a list of inspirational quotes and absorb them all at once. They have to arrive when you need them. Which means you have to keep reading, keep collecting, keep exposing yourself to other people's wisdom. So that when your moment comes, the right words are available.
But - and this is crucial - the quotes are training wheels. They help you balance until you learn to ride on your own. At some point, you develop your own wisdom. Not from quotes, but from experience. From the thousand small decisions you make while building something. From the failures you survive and the successes you earn and the patterns you start to recognize.
I still collect quotes. Still find new ones that resonate. But I rely on them less now than I did at thirty. Not because they're less valuable, but because I've internalized some of what they teach. The quotes point you toward certain truths. But eventually you have to discover those truths yourself. Nobody else's wisdom is a substitute for your own.
What I'd Tell Younger Me
If I could go back and give my twenty-five-year-old self one quote, one piece of guidance, it would be this: "Do not go where the path may lead, go instead where there is no path and leave a trail." Emerson said that. Or it's attributed to Emerson. Again, attribution matters less than truth.
I spent my twenties following paths other people had laid out. School, university, career, progression. All the normal steps. They weren't wrong, exactly. But they weren't mine. I was optimizing for what others thought success looked like rather than what success meant to me.
The trail I eventually left - starting Tallyfy, building this quotes site, writing poetry, thinking about how work should work - that's mine. Nobody handed me a map for it. There wasn't a career path called "build workflow software and collect quotes." I had to make it up as I went. That was terrifying and liberating in equal measure.
Twenty-five-year-old me needed permission to make things up. To not have a plan. To trust that if you walk in a direction that feels right, a path emerges behind you. That's what Emerson's quote means. Not that you need to do something unprecedented - most things have been done. But that you need to do things your way, for your reasons, with your perspective. That's what creates the trail.
The Quote I'm Living Now
These days, the quote I return to most is from Mary Oliver: "Tell me, what is it you plan to do with your one wild and precious life?"
I'm fifty now. More behind me than ahead. That question hits differently at fifty than it did at thirty. It's not hypothetical anymore. It's not "what do you want to do someday?" It's "what are you actually doing right now?" Because right now is all there is. The wild and precious life isn't waiting in the future. It's happening. Today. This year. While you're busy making other plans.
So what am I doing with it? Building a company that makes work less chaotic. Maintaining this collection of quotes that helps people find wisdom. Writing essays and poetry. Trying to think clearly about what matters. Not changing the world - I'm not that ambitious. Just making my corner of it slightly better, slightly more thoughtful, slightly more human.
That's enough. It has to be. Because you can spend your whole life planning for some future where you'll finally do the important work, or you can do important work now with what you have. The quotes that shaped my path all pointed toward the same truth: Start. Try. Fail. Learn. Keep going. The path emerges from walking it. The wisdom emerges from living it.
These are the words that guided me. They won't guide you the same way. You need to find your own. Read widely. Collect what resonates. But remember: The quotes are signposts, not destinations. They point you toward certain truths, but you have to walk the path yourself. You have to do the work. You have to live the questions until you earn the answers.
And then, if you're lucky, maybe someday someone will quote you back to yourself. Not because you're famous, but because something you said happened to be what they needed to hear exactly when they needed to hear it. That's how wisdom propagates. Person to person. Moment to moment. One wild and precious life at a time.