Imposter Syndrome Has Cost Me THOUSANDS… Let’s Talk About It.

Imposter syndrome has cost me thousands—and honestly, I’m willing to bet it’s cost you a pretty penny too. Today, I want to share four specific ways imposter syndrome has impacted me financially. Actually… if I’m being real, it’s probably cost me tens of thousands.

This topic has been on my mind for a while. When I first came up with the idea for this podcast, this was one of those “Ooh, maybe someday” episode ideas. And it’s been sitting in the drafts for—what?—16, 17, maybe even 18 months. Wild.

So why now? Why dust it off today? A few things, really. One big one: I was recently chatting with a couple of other business owners. We got on the topic of investments—specifically coaching in this case, but this conversation goes beyond just that.

Everyone was sharing how much they were investing—and it was a lot. And as someone who has probably overinvested in education, especially in the early years… well, let’s just say I’ve learned a thing or two. I’ve been in business for eight years now, and those first six? Yeah, I definitely overdid it.

I’ll go into more detail, but that was one of the key things that made me realize: it’s time to talk about this.

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Imposter syndrome has this sneaky little way of costing us a lot of money. And most of us kind of know that—maybe we’re not charging what we’re worth, maybe we’re over-delivering for clients, not setting boundaries, all that kind of stuff. And yes, all of those are totally valid.

But today, I want to talk about four very specific ways imposter syndrome has literally cost me thousands—not just in missed opportunities, but in actual dollars spent or lost. So, let’s get into it.

1. Investing in Multiple Courses (On The Same Thing!)

So, number one: imposter syndrome cost me thousands by pushing me to invest in courses I didn’t actually need. And I’m talking a lot of courses. Honestly, you could swap in “coaching” here too.

I even had a note to myself—this topic’s been in my drafts for over a year—to try and count how many Pinterest courses I’ve bought. There were so many. I tried to track them all down before recording this episode, but between all the different email addresses and business names I’ve had—Love at First Travel, then working under my own name, then The Kara Report—I couldn’t find them all. But off the top of my head? I know I’ve bought at least six Pinterest courses.

Now, in some ways, I could justify it. Like, yeah—it’s important to know what you’re doing before offering Pinterest as a service. I still believe that. But a lot of it, if I’m being really honest, came from this mindset of: What am I missing?

Sometimes we’re just so naïve in the online space. We believe everyone else is getting better results than we are—but really, they’re just good at marketing. I followed Pinterest managers who made it look like they had dream clients, perfect results, all those green analytics screenshots, millions of impressions… And I was sitting there thinking, Why am I not getting those results? What am I doing wrong?

Valuing Education While Needing a Balance

And again, I do think education is valuable. But did I need six Pinterest courses? No. I probably needed one solid mentor to walk me through their process, then I just needed to buckle down and do the work—testing, tweaking, experimenting with my own account or, transparently, on client accounts.

Instead, I spent all this time consuming content—podcasts, courses, trainings—when I could’ve been doing. And it wasn’t just Pinterest. I did the same thing with other areas of my business too. For example, I bought three website copywriting courses—three!—before I finally felt confident enough to offer website copy as a service. And look, those courses weren’t useless. I learned a ton. And as a copywriter, sure, maybe I needed more technical depth than most. But did I need three? No. That was imposter syndrome convincing me I wasn’t ready.

There was even one time—I don’t even want to say the number, it’s that embarrassing—but I bought this huge bundle of courses for a service I was convinced I wanted to offer. I thought, This is it. This is how I’ll finally hit my income goals. And then… I realized I didn’t even want to offer that service. Total waste of money.

And while that might not technically be imposter syndrome, in a way it was. I didn’t believe I could succeed on my own path, so I tried to replicate someone else’s. I thought the only way to reach their level of success was to do exactly what they were doing—even if it meant completely rearranging my business.

So yes, I believe in investing in yourself—in your skills, in mentors, in learning from people who’ve been where you want to go. But at the same time, this has been one of the biggest ways imposter syndrome has cost me thousands. I bought into the idea that other people had some secret I didn’t. I believed they were getting better results, so I kept buying courses trying to make sure I knew everything there was to know… about everything.

2. I Kept A Software That I Wasn’t Using Because I Thought It Would “Look Bad”

Alright, the next one is a super quickie—but it’s such a clear, practical example. You’re going to picture this immediately.

So, when I decided I didn’t want to do destination wedding planning anymore—just for context, I used to run a destination wedding planning business. It still exists today, but I don’t work in the business directly anymore. These days, I handle the blogging and Pinterest side of things—go figure!

Keana, who now basically runs the show, handles all the travel coordination. She doesn’t do the actual wedding planning, just to clarify—though just is doing a lot of work there, because travel coordination is no small task. So if you’re having a destination wedding, she’ll handle your travel and all your guests’, then put you in touch with the resort’s coordinator for the flowers, cake, all that fun stuff.

Anyway, here’s where the money part comes in. Back during the pandemic, when weddings were on pause, I was still paying for Aisle Planner—a wedding planning software. And if you don’t know it, Aisle Planner is expensive. Like, really expensive. And listen, if you’re actively using it, I’m not saying it’s not worth it. But… I wasn’t using it.

I had a couple of clients with access, but I could literally see that they weren’t using it either. Still, I kept justifying the cost to myself—telling myself it was a value-add, something nice to offer clients.

Then I did the math. While no one was using it, I spent just shy of $2,500 on this software. Why? Because I didn’t want to send an email saying, “Hey, we’re canceling this subscription nobody is using.” I was afraid it would make the business look like it was struggling or like we were being cheap. I didn’t want it to seem like we were cutting corners.

So I just… didn’t cancel it. Even though I knew it wasn’t being used. And that one little decision ended up costing me $2,500. Honestly, I think I’m being generous with that number. I’m not even counting the months I spent debating whether to cancel or the transition months where I started easing people off of it. I’m literally just counting the months where nobody logged in.

But I had this fear that one of those clients might one day randomly log in and be like, “Hey, where’d it go?” So I kept paying for it. All because I didn’t want the business to look a certain way.

And that’s just one example—but I’d bet money (see what I did there?) that you’ve faced or will face a similar situation. That uncomfortable moment where you’re like, “Ugh, I don’t want to do this because… what if it looks bad?”

Ask yourself: Is this just imposter syndrome? Insecurity? Fear of perception? Because if it is, it might be quietly costing you money too.

3. Being Too Afraid To Say “No” and/or Over-delivering

Alright, this third one’s a bit longer, it’s about being too afraid to say no—or not being fully transparent about expectations—because I didn’t want to look like I didn’t know what I was doing.

Let me back up a bit. Earlier, I mentioned one of the inspirations for this episode was a conversation I had with some business friends. We were all talking about how much we’ve spent on coaching, and it hit me—like, wow, we’re all out here spending a lot of money trying to make sure we’re doing things “right.” And I’m not excluding myself here. Even among a group of women who really know what we’re doing, we were all investing so heavily—because we want to get it right, grow, stay aligned, all of that.

The second inspiration for this episode came from a post I saw on Threads. Someone had shared something like, “My Pinterest manager’s been working on my account for X months, and I’ve only gotten X number of link clicks.” Now, the post itself wasn’t the issue—but the comments were.

Gaining Experience Means I’m OK Admitting I Know Less

It was filled with other Pinterest managers chiming in like, “Whoa, that’s way too low,” or “When I run accounts, I get XYZ amazing numbers.” And listen—maybe those numbers are real. Maybe they’re best-case scenarios. But the vibe was: “That Pinterest manager must not know what they’re doing.”

And here’s the thing. I used to think like that. I’d see those results and think, “Wait, what am I doing wrong?” But now? If you’re only sharing your best client results and positioning them as the norm, I don’t assume you’re amazing—I assume you just haven’t been in business long enough to know better. That might sound harsh, but here’s what I mean:

In my early Pinterest days, I’d tell clients, “It takes 3 to 6 months to see traction.” Now? I say 6 to 12. Not because I’ve gotten worse—but because I’ve gotten more experienced. I’ve seen how long it actually takes for some accounts to start performing, especially when you factor in niche differences, business model alignment, or just the unpredictable nature of Pinterest itself.

There are outlier accounts that pop off fast. I had one recently that got 2,500 clicks in three months. But that is not typical. A lot of factors aligned. I’d never use that result in marketing like, “Hire me and this is what you’ll get.” I’d rather under promise and overdeliver every time.

So, how does this tie back to imposter syndrome costing me money? Because I used to overpromise. I was too afraid to say no or set realistic expectations, because I didn’t want to seem like I didn’t know what I was doing. And since integrity is really important to me, I would then turn around and over-deliver to make up for it—working double or triple the time, sometimes for what probably worked out to $4/hour, just to live up to promises I never should’ve made.

Let me give you a clearer example. People would ask if I could do things like write email funnels, and I’d say, “Yes, absolutely!”—even if I’d never done one before. Then I’d go buy a course, spend 25 hours obsessing over every word in that welcome sequence, trying to make it perfect. And all of that came from imposter syndrome—not because I wasn’t qualified, but because I didn’t believe I was enough without over-preparing, over-delivering, and proving myself over and over.

Even if I already had the knowledge, it never felt like enough.

Now, because I’m so much more confident in what I do know, I can say things like, “Hey, I don’t know much about email funnels.” Or, “Sure, I can write one for you because I understand your brand and I’ve done your website copy—but if you’re looking for a true specialist, [insert expert’s name] might be a better fit.”

And the truth is, in the earlier stages of my business, I wouldn’t have been able to say that. But now I can confidently explain not just what my skillset is, but also what it isn’t. Or maybe even more importantly—what I actually want to do. Because sometimes it’s not about ability, it’s about desire.

So maybe this is where imposter syndrome and people-pleasing start to blend together. (And let’s be real—I still struggle with people-pleasing, so don’t expect an episode on that anytime soon.) But the point is: this hesitation costs money.

But that’s the thing: imposter syndrome has cost me money not only by pushing me to learn skills I never really wanted to learn, but also by eating up so much of my time. And as your business grows, your time becomes your most valuable resource.

Eliminating Services and Going “All In” On Pinterest and Blogging

Actually, just earlier tonight, I was chatting with a friend about our visions for the next year. And with a few different things going on—like teasing my new branding and rebuilding my website—I’ve been digging into keyword research, seeing what I rank for now, and thinking about what I want to rank for.

One of the things I rank for on page one is “website copy VIP day” and “website in a weekend.” Which is great! Those were real services I used to offer—I’d write the copy, plug it into a Showit template or whatever platform the client used. I’m not a designer, but I can work with templates just fine.

So now I’m looking at the data, and I’m like: okay, I’m getting good traffic, but not a ton of inquiries. The “logical” thing to do would be to optimize that sales page, add more testimonials, tweak the pricing, look at conversions—all of that.

But the truth? I don’t want to book more of those services.

And even though it’s exciting to rank on page one for anything, I’m scaling back. I’m going all in on Pinterest and blogging—those are my bread and butter services. I still take on extra projects for current clients—if you’re one of them and want a welcome email or something, I’ve got you! But I don’t want to bring in new clients for these one-off or side services. That’s not the direction I’m going in.

4. Not Charging “Enough”

And that brings me to the fourth and final way imposter syndrome has cost me thousands: pricing.

I teased earlier that this episode wasn’t about not charging enough—but surprise! It kind of is. Because the truth is, even now, I still hesitate to charge as much as others who I know are equally qualified. And I’m not talking about guessing—I have the receipts. I’ve been doing this work for five solid years. I have case studies, I have results, I know the impact I create.

Am I the best at asking for testimonials? Absolutely not. But I know my long-term clients would vouch for me in a heartbeat. I’m probably going to do a little testimonial outreach batch before the new site goes live. Like, “Hey, we’ve been working together for three and a half years… would you mind leaving a quick review?”

A lot of my clients don’t even offboard—which is amazing, I love that. But it also means I don’t have those natural moments built into my process to ask for reviews. So that’s something I’m working on.

Anyway, the bottom line is: I know I get powerful results. I have clients who shout about me from the rooftops. And yet… pricing can still be hard. That’s the imposter syndrome talking. That little voice that says, “Are you sure you can charge that much?”

And the truth is, I am sure. I just have to keep reminding myself—and maybe you do too.I know I have amazing clients—like truly, the best. They refer me constantly, they’re loyal, they’re kind… I’m really lucky. So if I had to name the last way imposter syndrome has cost me money, it’s this:

Despite all of that, I still struggle with raising my prices to match what many of my peers or competitors are charging.

And actually—let me be real for a second. I recently saw someone I loosely follow offering a group program. It was teaching something that, if someone hired me to do it for them, I would’ve charged $400/month—and done it for five solid months—for the same price as this one course. That’s $2,000 for a program… when they could’ve had five months of hands-on support.

And my first reaction was like, What?! How is this not a no-brainer to just outsource it to me? But that’s when I realized: clearly, it’s not a no-brainer. And that’s on me.

I’m not doing a good enough job communicating my value. Not just that I’m good at what I do—but that I care, I’m invested, I’m affordable… and I genuinely get results.

I have packages that start at $275/month. For done-for-you services. From someone who’s going to be in your business with you, thinking strategically, showing up consistently, and cheering for your wins. Like… hello?? Why am I still hesitating to raise my prices?

I think it comes down to this: ROI is important to me. I want to know that people are getting value, and sometimes imposter syndrome whispers, What if they don’t? Even when I have proof that they do.

Okay—I’m going to rein this in, because I could spiral off in a million directions. Let’s keep it focused.

Is Imposter Syndrome Costing You Money?

Here’s the recap—these are the four ways imposter syndrome has cost me thousands:

1. Investing in courses or programs I didn’t really need—because I thought I needed to “know more” to be worthy.
2. Being too afraid to say no or set clear expectations—so I over-delivered and worked for far less than my time was worth.
3. Holding onto software or tools I wasn’t using—because I didn’t want it to look like I was cutting back.
4. Not charging enough or hesitating to raise prices—even when I had the experience, the receipts, and the referrals to back it up.

And I’m willing to bet imposter syndrome is costing you somewhere in your business too.

Now, I don’t have a magic 8-step solution for this. I wish I did. But I do believe that awareness is the first step—and that naming it can start to loosen its grip a little.

So thank you. Truly. Thank you for letting me talk at you for 25 minutes. That feels wild. And thank you for sticking around to the end.

If you liked this episode, I would love love love if you’d leave a review—or even just shoot me a message on Instagram to let me know what resonated. I appreciate you so much, and I’ll talk to you next week.

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