Working hard should lead somewhere. But what happens when decades of effort don’t create the security you expected? This is my honest look at what happens when loyalty, people-pleasing, and comfort quietly replace ambition. If you’ve spent years working hard for others and wondering why you’re still stuck, here’s what I’m learning about working hard for yourself instead of everyone else.
What Nobody Tells You About Working Hard: When Effort Doesn’t Equal Progress
Table of Contents
The Gap Nobody Talks About
We’re told hard work pays off. Show up every day, do good work, be reliable, and eventually it adds up to something. Your effort compounds. Your loyalty gets rewarded. Your dedication creates security.
But what happens when you work hard for decades and you’re still… here? Same financial struggles, same uncertainty about the future, same sense that you’re treading water instead of moving forward.
Not broke. Not desperate. Just stuck in a way that doesn’t match the effort you’ve put in.
I’m 57, living paycheck to paycheck, still trying to figure out how decades of work didn’t translate into the stability I thought it would. And I’m wondering if the problem isn’t how hard I worked, it’s how I worked, and more importantly, for whom.
Have you ever worked hard for years and wondered where the payoff went?
The Back Seat Syndrome
Here’s what actually happened: somewhere along the way, ambition got replaced by people-pleasing and taking the comfortable option. I worked hard, but I did it sitting in the back seat, waiting for other people to become successful and somehow lead me to a better place.
I made myself useful to good people. I stayed loyal to them. And I told myself that was enough, that being part of someone else’s success counted as my own success.
But it doesn’t. Not really.
For twenty years, I’ve worked alongside the same good, kind people. They appreciate me genuinely. But I’m helping them build their lives while I’m still figuring out how to build mine. That’s not their fault. I chose the passenger seat. Because small ponds feel safer than oceans. Because working for others feels more honorable than working for yourself.
Have you spent years supporting other people’s dreams while your own stayed on the shelf?
Why We Choose Comfort Over Growth
Fear disguised as humility. “Who am I to think I could build something big?” feels like modesty, but it’s actually fear. Fear of failing publicly. Fear of trying and proving you’re not as capable as you hoped.
People-pleasing as borrowed purpose. When you make yourself useful to others, you feel needed. That’s a form of purpose. It’s just not YOUR purpose. It’s borrowed from someone else’s mission.
Comfort as self-protection. Small ponds are predictable. You know you won’t fail dramatically because you’re not attempting anything dramatic. Safe feels like wisdom when you’re scared.
Success anxiety. What if reaching the top wouldn’t actually make much difference? What if you got the money, the success, the recognition… and you were still you, with the same doubts? Sometimes staying stuck protects us from finding out that success wouldn’t fix us anyway.
Did you avoid going after what you wanted because part of you didn’t believe it would matter?
What Nobody Tells You About “Good Work”
Here’s what they don’t tell you: you can be excellent at your job, reliable, dedicated, genuinely valued, and still not move forward. Because being good at what you do and building something for yourself are completely different things.
Working hard for others: Show up consistently. Be dependable. Do quality work. Support someone else’s vision.
Working hard for yourself: Take risks that scare you. Build something that might fail. Prioritize your vision over comfort. Bet on yourself instead of waiting to be chosen.
Both are hard work. But only one builds YOUR future.
I’m currently reading “What’s Your Dream?” by Simon Squibb with my boss during our English lessons. Simon makes a point that surprised me: hard work is only part of the equation for success, but not necessarily the main part. That hit differently than I expected. Because if hard work alone doesn’t create success, then what does? Vision? Risk-taking? Strategic choices? Asking for help? All the things I avoided by staying comfortable and working hard for others instead of myself.
I wrote about how dreams change as we get older, and how they shift from adventure and ambition to something quieter, and more realistic. Maybe my dreams got smaller because I chose comfort over the bigger equation Simon talks about.
Maybe that’s why I stayed stuck. I focused on the one ingredient (hard work) while missing the others entirely.
Are you working hard at the wrong things?
The Selfish You Didn’t Become
I keep thinking about that word: selfish. It feels wrong. But maybe what I needed was to be more self-focused instead of other-focused. To work hard for MY dreams instead of alongside other people’s dreams. To work to people-please my future self instead of people-please my current colleagues.
Once, in my twenties, I chased something purely for myself. I trained as a helicopter pilot. Nobody benefited but me. And I made it happen because I wanted it badly enough to sacrifice comfort for it.
But then I spent the next twenty-plus years being unselfish. Supportive. Loyal. Comfortable. Working hard in ways that focused on serving others, yet somewhat drifting, not molding myself into a better version for the future.
What version of yourself did you abandon by being too selfless?
The Help I Can’t Ask For
Here’s something else I’m realizing: I need to work with successful people, not just good people. People who can lift me, not just appreciate me. And I probably need to ask for help, real help. Maybe even financial assistance to help with a fresh start or begin a project.
Some successful people started by asking family for a small loan to get off the ground or chase a dream. I’ve never done that. I don’t know if it’s pride, shame asking at this age, or just not wanting to burden anyone. But that fear of asking might be keeping me stuck as much as anything else.
When I scroll social media, I’m drawn to successful people and their advice. Part of me hopes that having a blog, building an online presence, will somehow be seen as proof of my potential, my sincerity, my willingness to work. Like maybe if I document my journey honestly enough, someone will notice and offer a hand up. Maybe the current 616 Duolingo day streak can demonstrate a willingness to show up daily, even if just for 10 minutes.
I imagine many people feel like that. They know their energy and passion are real, but they can’t figure out how to translate that into opportunity. They want to work WITH successful people where both parties lift each other and benefit, and not just work to be kind and helpful while never getting lifted themselves.
But here’s the truth: nobody’s coming to save you just because you have a blog or post consistently or show up with good intentions. Opportunity doesn’t find you, you have to create it. Or at least ask for it.
Are you waiting to be discovered, or are you afraid to ask for what you need?
The Uncomfortable Truth
The gap between effort and outcome creates a kind of shame that’s hard to admit. Because if you worked hard and didn’t succeed, what does that say about you?
Or maybe it just means you chose loyalty over ambition, comfort over risk, serving others over building for yourself, and now you’re living with the consequences of those choices.
I’m embarrassed that decades of work didn’t create more security. Frustrated that being into technology for years hasn’t translated into income. Confused about whether I worked hard at the wrong things, or just worked hard in the wrong way.
Have you dug yourself a hole not through laziness, but through misplaced effort?
How To Work From Here On Out?
I don’t have the answer. I’m still figuring out what “working smarter” looks like at this age. But I do know this: working hard isn’t enough if you want to build something for yourself.
At some point, you have to get selfish. You have to stop waiting in the back seat for someone else to drive you somewhere better. You have to work hard for YOUR vision, even if it’s uncomfortable, even if you might fail.
Because the alternative – working hard for decades and ending up stuck.. isn’t working.
What would change if you worked as hard for yourself as you’ve worked for everyone else?
How Hard Have You Worked For Yourself? What’s Your Experience?
Maybe you’ve worked hard for years and stayed loyal, dependable, and valuable to others, yet wondered why the payoff never came. Maybe you chose comfort over ambition and now question that choice. Maybe you’re embarrassed by the gap between your effort and your outcome.
Or maybe you figured this out earlier than I did. Maybe you learned to be selfish in the right way, to bet on yourself, to work hard for your own vision. Did you wait until middle-age before you decided to work differently?
Give me some advice, or let me know your journey: Have you worked hard at the wrong things? Did people-pleasing replace ambition somewhere along the way? Are you still waiting for your turn, or did you finally take it?
I explore the possibility that success might be dependent on a more spiritual foundation, too, if that resonates with you and your feelings about working hard.
One More Thing:
I don’t want this to come across as a rant or pity party. The people I work with and have worked for are genuinely great people who’ve supported me, and I’m grateful for that. This is just me recognizing that I spent years expecting success to happen through hard work and loyalty alone, when really, it needs to be actively pursued. That’s on me, not anyone else.
Share your thoughts below. I respond to every comment, and your experience often helps others more than mine does.
