The Top 5 Career Mistakes I’ve Made (That I Hope You Don’t Make)

Show notes
Before I get started, let me mention that I’m offering The Smarter Accountant CPE course “The Smarter Accountant Guide to Effective Time Blocking” for the last time this month on Wednesday, August 27th at 12 pm EST.
This is a powerful course because the way I teach time management is not like anyone else. I blend brain science with time management so that you can learn how to manage your time more effectively and get more done in less time.
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We all make mistakes in our careers. It’s just part of the process. I’ve been in public accounting for over 35 years and I have yet to meet an accountant who says their career has been exactly what they hoped it would be.
Sometimes you know you’ve made a mistake right away. Other times, it takes years to realize something wasn’t working.
Looking back, there are things I wish I had done differently. Not because I did anything “wrong,” but because I didn’t know there was a better way.
When you’re busy trying to keep up, it’s hard to step back and ask if the way you’re doing things is actually helping. Most of us are just trying to get through the week.
No one really teaches you how to have a career that fits your life. You’re usually taught how to get the work done, not how to feel good doing it.
You figure it out as you go, and sometimes that means falling into patterns that aren’t helping. Even when those patterns seem normal, they might be slowly burning you out.
What makes it tricky is that many of the things we do as accountants are praised by others. You might get compliments for working late or taking on more, even when it’s hurting you.
That’s why I think it’s important to talk about the mistakes that sneak up on us—the ones that feel like the “right” thing to do at the time.
Have you ever kept doing something just because it’s what you’ve always done, even if it no longer makes sense? It’s easy to fall into that trap without even realizing it.
It took me a long time to figure out that just because something is common doesn’t mean it’s smart. And just because it works for someone else doesn’t mean it’s right for you.
These kinds of mistakes aren’t about technical skills. They’re about how we approach work, decisions, and the way we treat ourselves.
That’s why I wanted to open up and share some of the bigger things I wish I had learned sooner. Not to look back with regret—but to help you move forward with more clarity.
If you’ve ever felt like your career doesn’t quite feel the way you hoped it would, you’re not alone. And it might not be that you’re doing anything wrong—it might just be that no one showed you another way.
So the real question is—what if you didn’t have to make the same mistakes? What if one small shift could help you feel more in charge of your career and your life?
Let’s talk about it.
Mistake #1: Working Off a To-Do List
For a long time, I truly believed my to-do list was helping me. I’d write everything down—every task, every reminder—and I’d get a little thrill each time I crossed something off. It felt productive. It felt like I was staying on top of things. But the truth was, I was just staying busy.
My list never actually ended. Most days, I just moved things from one list to another. I’d knock out a bunch of small tasks and still feel behind. I wasn’t deciding what mattered—I was reacting to whatever looked easiest or most urgent in the moment.
What I didn’t realize back then was that my brain loved the illusion of progress. Checking boxes gave me a quick sense of relief. But I wasn’t making meaningful progress on the things that actually moved my career forward or supported the life I wanted outside of work.
If I could go back, I would tell myself that a to-do list isn’t a plan—it’s a collection of random thoughts. It’s not meant to guide your day. What really matters is learning to decide—ahead of time—what deserves your time, energy, and focus.
Smarter accountants don’t rely on lists. They learn how to calendar effectively. And that one shift can change everything.
Mistake #2: Not Defining What’s “Enough”
For years, I kept pushing myself without ever asking, “When will it be enough?” More clients, more work, more hours—I just kept going. I told myself that once I hit a certain point, then I’d feel better. Then I’d feel successful. Then I’d slow down.
But that point never came. No matter how much I got done or how many goals I reached, it always felt like I should be doing more. There was always another project, another request, another reason to keep pushing.
The mistake wasn’t in wanting to grow—it was in not setting a clear stopping point. Without a personal definition of “enough,” I was chasing something I couldn’t see. And that kind of chase never ends. It just leads to burnout, stress, and the feeling that you’re always behind, even when you’re actually doing a lot.
And for a long time, that included chasing more money. I thought I had to say yes to every opportunity because turning it down felt irresponsible. But over time, I’ve learned something really powerful: I’ve started turning down extra work—not because I can’t do it, but because the promise of more money just doesn’t appeal to me the way balance does.
The irony is that the more I’ve focused on “enough,” the more money I’ve actually made—and I’ve done it while keeping that balance I used to only dream about. It turns out that when you stop chasing everything, you create space for the right things to grow.
If I could go back, I’d sit myself down and ask, “What does enough look like—for me?” Not what other people say. Not what the industry expects. Just my own version of a full, balanced life. I didn’t realize that defining enough gives your brain permission to stop reaching and start appreciating.
Smarter accountants don’t let “more” be the goal. They decide what’s enough and let that guide their choices. Because once you know what you’re aiming for, you can finally rest when you get there.
Mistake #3: Not Defining Success
When I first started my career, I had a vague idea of what success looked like. I figured it meant working at a good firm, climbing the ladder, making a solid income, and being seen as someone who had it all together. That’s what I chased—without ever stopping to ask if that version of success actually felt good to me.
Getting hired by Deloitte right of college felt like success at the time. Passing the CPA exam felt like success at the time. Moving up the corporate ladder felt like success at the time.
I kept hitting milestones that were supposed to matter, but something always felt off. I’d reach a goal and think, “Is this it?” It looked impressive from the outside, but inside I felt tired, disconnected, and unsure if I was even on the right path.
The mistake was letting the outside world define success for me. I never took the time to decide what my version looked like. So I kept checking off boxes that didn’t actually lead to the kind of life or work I wanted. It was like running a race I didn’t remember signing up for.
If I could go back, I’d ask myself a simple question: “What does success feel like, not just look like?” Because it’s not just about achievements—it’s about how you want to live, how you want to feel, and what actually matters to you.What I’ve learned is that success isn’t one-size-fits-all. It’s not about what your title is, how many hours you bill, or how full your calendar is. It’s about building a career that fits the life you want—not the other way around.
Smarter accountants define success for themselves. And once you do that, everything changes. You stop chasing and start choosing. You stop comparing and start aligning. And that’s when success starts to feel like something you actually want to keep.
Mistake #4: Not Getting Clear on Life Priorities and Values Early On
In the beginning, I made career decisions based on what looked good on paper. More money? Great. Bigger title? Even better. I didn’t stop to ask what actually mattered to me. I just followed the path that seemed smart and responsible.
What I didn’t realize at the time was that I was building a career that looked successful but didn’t feel right. I was saying yes to things that didn’t leave room for the life I actually wanted—things like quality time with family, my health, creativity, or just a little breathing room.
The mistake wasn’t in being ambitious. It was in letting my career take over without ever checking if it matched the kind of life I wanted. I felt pulled in different directions. Like I was doing “the right things” but losing pieces of myself in the process.
If I could go back, I’d ask myself to write down what matters most in my life—before making big career decisions. Not just goals like saving for retirement or paying the mortgage, but deeper values like peace, connection, freedom, or joy.
I’ve since learned that your accounting career should support your life, not run it. You don’t need to choose between being a good accountant and being true to yourself—you just need to know what your priorities are and let them lead the way.
Smarter accountants start with life in mind. They get clear on what matters most and use that clarity to make smarter choices at work. And when your work supports the life you want, it stops feeling like a constant tug-of-war.
Mistake #5: People-Pleasing
For a long time, I said yes when I wanted to say no. I answered emails late at night, took on extra work I didn’t have time for, and tried to make everyone happy—clients, coworkers, even people I barely knew. I thought being helpful meant being available all the time.
At first, it felt like the right thing to do. I got praise for being dependable and easy to work with. But underneath it all, I was exhausted. I was constantly putting other people’s needs ahead of my own and ignoring the quiet voice in my head that kept saying, “This isn’t working.”
The mistake was thinking that being nice meant never disappointing anyone. But people- pleasing isn’t kindness—it’s self-abandonment. It taught others that I was always available, and it taught me that my own time, energy, and needs didn’t matter as much.
If I could go back, I’d tell myself that boundaries aren’t selfish—they’re necessary. I didn’t need to be rude or distant to protect my time. I just needed to stop assuming that saying yes was the only way to be valued.
What I’ve learned is that people-pleasing doesn’t actually please anyone in the long run. It leads to burnout, resentment, and feeling like you’re never doing enough.
Smarter accountants know that you can be kind without being a pushover. You can be professional without being available 24/7. And you can respect others without constantly sacrificing yourself.
The Brain Science Behind These Career Mistakes
One of the biggest things I’ve learned over the years is that most of the mistakes I made weren’t because I was doing something “wrong.” They were because my brain was doing exactly what it’s wired to do.
Our brains are built for safety and survival, not for modern-day success in a demanding career. They like what’s familiar—even if what’s familiar is stress, overworking, or saying yes when you want to say no.
Your brain is constantly scanning for danger, and in today’s world, that “danger” often shows up as things like disappointing someone, missing an email, or not meeting a deadline. So it nudges you to avoid discomfort and play it safe, even if that means repeating old habits that aren’t helping.
It also wants quick wins and easy rewards. That’s why checking off a to-do list feels so good, even when the tasks don’t really matter. It’s why praise from others feels important, even when it pulls you away from your own goals.
The brain loves short-term validation more than long-term fulfillment. So it pushes you toward what feels good right now—approval, achievement, staying busy—even if it leads to burnout later.
That’s what was happening in every one of the career mistakes I made. Overcommitting, people pleasing, chasing success that wasn’t mine—all of it made perfect sense to my brain. It was just trying to keep me safe, liked, and comfortable.
But here’s the truth: becoming a Smarter Accountant means you stop letting your brain run the show. You learn to manage it instead of follow it.
And once you start doing that, everything begins to shift. You’re no longer stuck in survival mode—you’re making conscious decisions that truly work for you.
Becoming a Smarter Accountant: Learning From Career Mistakes
I worked with a client who was deep into her career and doing all the “right” things—at least on the surface. She had a steady stream of clients, worked long hours, and was constantly trying to prove she was reliable and capable. From the outside, she looked successful.
But behind the scenes, she was exhausted. She had no clear boundaries, no time to think about what she wanted, and no idea what “enough” looked like. She was checking off endless tasks, saying yes to everything, and felt guilty anytime she even thought about saying no.
When we started working together, she realized she had never stopped to define what success actually meant to her. She’d been following a path she didn’t choose—one that left very little room for rest, family, or anything outside of work.
As she started learning how her brain was driving those old patterns—like people pleasing and chasing constant productivity—things began to shift. She learned to notice those thoughts without letting them take over. She practiced making decisions based on her values, not her fears.
And over time, she began to do something that felt impossible before: she started turning things down. She let go of work that didn’t align with her goals. She created space for herself. And instead of losing money or momentum like she feared, she actually became more focused, more effective, and more fulfilled.
Her calendar looked different. Her energy felt different. And most importantly, she felt different—more in control, more confident, and more at peace.
Now I’m going to share the key takeaway from today and an action item for the upcoming week.
Key Takeaway and Action Item
The mistakes we make in our careers often come from not questioning the default settings in our brain. When we don’t define what’s enough, what success really means, or what matters most to us in life, we end up following someone else’s path. But once you start managing your mind instead of letting it run on autopilot, everything can change—for the better.
This week ask yourself, “Am I building a career that supports the life I want—or one that’s just happening by default?”
This question is meant to help you pause and reflect. So many accountants stay on a path simply because it’s what they’ve always done or what others expect.
But when you slow down and ask yourself if your career is actually supporting the life you want—whether that means more freedom, less stress, or more meaning—you give yourself the chance to make a smarter choice moving forward.
The bottom line is that we all make mistakes, and every one of these taught me something important. The good news is, you don’t have to wait years to learn these lessons.
You can start making different decisions today—ones that reflect who you are and the life you want. That’s what being a Smarter Accountant is all about.
Pulling Back the Curtain
Pulling back the curtain…
There was a point in my career when all five of these mistakes were happening at the same time—and I couldn’t see it. I was working off an endless to-do list, saying yes to everyone, chasing success without really knowing what I wanted, and constantly ignoring what mattered most in my life.
From the outside, it looked like I was handling it all. But inside, I was burned out. I was drained, snappy with the people I loved, and questioning whether this was really how my career was supposed to feel. I remember thinking, “If this is what success looks like, why am I so miserable?”
The turning point wasn’t some big, dramatic moment. It was a quiet realization that I didn’t want to keep doing things the same way.
I started questioning the thoughts that were driving my choices. I began to notice how often I was trying to prove something—trying to be everything to everyone while putting myself last.
What helped me most was studying to become a Professional Certified Coach and learning how my brain worked. Once I understood that my habits were based on fear, approval-seeking, and old beliefs, I could finally change them. I could finally make decisions from a place of clarity instead of guilt or pressure.
And I’m still practicing. I still catch myself tempted to add just one more thing to the list or to say yes out of habit. But now, I have the tools to pause, ask better questions, and choose differently. That’s what being a Smarter Accountant means to me.
So, if any part of this episode hit home for you, I want to invite you to take The Smarter Accountant Quiz. It’ll help you see where your brain might be running the show and where you have the most room for growth. You can find it at www.thesmarteraccountant.com.
And if you’re ready to talk about what’s next for you, I offer a free 30-minute call where we can explore what’s working, what’s not, and how you can start making smarter decisions in your career. Just go to www.thesmarteraccountant.com/calendar to grab a time.
Lastly, if you know another accountant who could use this episode—someone who’s smart and capable but maybe stuck in some of these same patterns—please share this with them. We all deserve to feel better about the work we do and the life we’re creating.
The truth is that you’re already smart. But this podcast, I promise, will show you how to be smarter.