364. Stop Optimizing for Pennies When You’re Losing Dollars

So… let me tell you a little story about a decision I put off for way too long — and the lesson it taught me about what “saving money” actually costs you in business.

On my course platform, they have these custom AI bots you can create to give access to your students. Pretty cool, right? The problem is, it’s not something you can purchase a la carte. It requires an upgrade to the next tier of service, which also comes with a bunch of shit I don’t actually need. So I hesitated. For a long time.

Instead of paying for features I didn’t need, I decided I was going to build the AI bots on a different platform and embed them into my community instead. Seemed smart. Seemed scrappy. Seemed like the kind of thing a smart business owner would do to avoid wasting money, right?

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Why the Cheapest Choice Isn’t Always the Best Choice

But of course, months went by and I couldn’t get it done. I tested a new platform and struggled to get it to do what I wanted. Then other things came up. Then more time passed. And the whole time, this thing just sat on my to-do list like a little digital troll, mocking me every time I looked at it.

Eventually I just decided to screw it, upgraded to the new version of my course platform, and guess what? I was able to launch the AI bot within a matter of minutes. All I had to do was check some boxes to tell it what content inside Circle it should use as its knowledge versus having to create all the knowledge docs from scratch.

I mean, I knew it was going to be a big project to create all that content myself, but I figured eh, it’s a one-time project and then I could save myself a bunch of money every month. 

The problem with that thinking was, it didn’t get done.

While this showed up for me at this moment about a tech product… This struggle goes well beyond just apps and tech tools. 

This is about the psychology of how we make decisions in our businesses. The false economy of “saving money” by doing it yourself. The mental trap of avoiding an expense that would actually move you forward.

So today, we’re talking about the real cost of cheap. Why trying to save money can end up being one of the most expensive mistakes you make. And how to know when it’s time to just pay up and move on.

The Real Cost of Cheap

Let’s start by talking about what “cheap” actually costs you. Because here’s the truth: when you’re trying to save money by doing everything yourself, you’re not just saving money. You’re spending something else. And that something else is usually way more valuable than the cash you’re trying to hold onto.

First up, time. And I’m not just talking about the hours you spend actually working on the thing. I’m talking about all the time you spend researching. Testing. Troubleshooting. Starting over. Watching YouTube tutorials at 1.5x speed because you’re convinced you can figure it out if you just find the right video.

In my case, I spent time researching different AI platforms. I signed up for trials. I tested different setups. I got on support calls. I built knowledge docs from scratch only to find out my bot wasn’t reading them properly. And then… life happened. Other priorities came up. And the whole project just sat there, half-finished, collecting digital dust.

How much time did I actually spend on this? I honestly don’t even want to calculate it. But let’s be conservative and say it was 10 hours. If my time is worth $200 an hour — and yours should be worth something in that ballpark too — that’s $2,000 worth of my time to try to save maybe $100 to $150 a month. The math doesn’t math, friends.

Then there’s mental energy. And this one is sneaky because it’s harder to measure, but it’s just as real. Every time you look at your to-do list and see that thing you’re avoiding, it takes up a little bit of your brain space. Every time you think about it and feel that twinge of guilt or frustration, that’s mental energy you’re spending.

Decision fatigue is real. Frustration is real. The constant mental load of “I still need to finish that thing” is real. And all of that is energy you’re not spending on the things that actually move your business forward.

And then there’s momentum. This is the big one. Every day you’re stuck in DIY mode is a day you’re not moving forward on revenue-generating activities. Every day that project sits unfinished is a day you’re not getting the benefit of the thing you were trying to build in the first place.

In my case, I wanted those AI bots to help my students get answers faster without having to wait for me to respond outside of regular business hours. That would have improved their experience, and freed up my time for higher-value work. But while I was busy trying to save money by building it myself, none of that was happening. The opportunity cost was massive.

And finally, there’s opportunity cost. What else could you have been doing with that time? What revenue could you have generated? What campaigns could you have launched? What products could you have created? What customer relationships could you have nurtured?

This applies to so many scenarios beyond tech tools. Think about it:

You spend weeks trying to “figure out” email automation instead of hiring someone or taking a course. Meanwhile, your subscribers sit there not getting nurtured, not generating sales.

You avoid hiring a $200/month VA because you “can’t afford it,” but you’re spending 10 hours a week on admin tasks that have nothing to do with growing your business. That’s 40 hours a month. If your time is worth even $50/hour, you’re losing $2,000 in opportunity cost to save $200.

You don’t invest in a course or a coach because it feels expensive, but you stay stuck for months — or years — trying to figure it out on your own. How much revenue did you not make during that time?

The real cost of cheap isn’t the money you save. It’s everything else you’re spending to avoid spending that money.

Why We Do This to Ourselves

So if the math doesn’t math, why do we keep doing this? Why do we convince ourselves that spending 20 hours to save $100 a month is a good idea?

Here’s the thing: I get it. I really do. Because I just did this exact thing in my own business.

Part of it is the guilt of “wasting money.” Paying for features you don’t need feels bad. It feels wasteful. It feels like you’re getting ripped off. And if you’re someone who values being strategic and smart with your money — which, let’s be honest, if you’re listening to this podcast, you probably are — then that feeling of wasting money can be really hard to swallow.

But here’s what I want you to consider: Is paying for a few features you don’t need really more wasteful than spending dozens of hours trying to avoid it? Is it more wasteful than the revenue you didn’t generate while you were stuck in DIY mode?

There’s also this illusion of control. “If I do it myself, I’ll know exactly how it works.” And sure, maybe that’s true. But do you actually need to know how it works? And even if you do, was it worth the time it took to learn?

And then there’s the one-time project trap. You tell yourself it’s “just a lot of work upfront” so it’s worth the savings. But then it never gets done. Because here’s the truth: one-time projects that aren’t urgent have a way of never actually getting finished.

If it’s not urgent and it’s not easy, it’s going to keep getting bumped down the list. And meanwhile, you’re not getting the benefit of the thing you were trying to create.

There’s also the sunk cost fallacy. You’ve already spent so much time researching, testing, and planning that it feels wasteful to not finish it yourself. So you keep going, even though it’s not working. Even though it’s taking way longer than you thought. 

But here’s the reality: the time you’ve already spent is gone. You can’t get it back. The only question that matters now is: What’s the fastest way to move forward from here?

Look, I’m the first person to tell you not to waste your money on shit you don’t need. There are tools out there that are completely unnecessary for most of us. There are service providers who sound great on paper but end up creating more work because now you’re managing them instead of just doing the thing yourself. There are courses that promise the world but don’t actually move the needle for your specific business. It’s a fine line, and sometimes it’s genuinely hard to tell whether something is a smart investment or just shiny object syndrome. I fully acknowledge that. There are no hard and fast rules here.

But here’s the thing: that healthy skepticism can also become an excuse to avoid investing in the things that would actually move your business forward. And that’s where we get stuck.

The Lesson: Stop Optimizing for Pennies When You’re Losing Dollars

So, what’s the lesson? Stop optimizing for pennies when you’re losing dollars. I know this can be hard to hear. You might feel dumb like I did when you finally come to this realization in your own business. But we all need to hear this. 

If you’re spending hours — or weeks, or months — trying to save a few bucks, you’re not being strategic. You’re being penny-wise and pound-foolish.

The math doesn’t math. If your time is worth $100 an hour, and it probably should be, spending 20 hours to save $100 a month is a terrible ROI. You’re spending $2,000 worth of your time to save $100. That’s not smart. That’s not scrappy. That’s just… not good business.

And here’s the kicker: that calculation doesn’t even account for the opportunity cost. It doesn’t account for the revenue you didn’t generate while you were stuck tinkering with the thing. It doesn’t account for the momentum you lost. It doesn’t account for the mental energy you wasted.

Speed matters in business. Every day you delay is a day your competitors are moving faster. Momentum compounds. But so does inaction.

When you’re stuck in DIY mode, you’re not just slowing yourself down. You’re actively falling behind. Because while you’re spending weeks trying to build the thing yourself, someone else is paying for the solution and moving on to the next thing.

Your zone of genius is not “figuring out every random tool.” You didn’t start your business to become a tech support specialist for yourself. You started your business to sell products, serve customers, and build something meaningful.

Every hour you spend trying to figure things out, is an hour you could be generating more revenue or spending time outside of your business. 

The best investment is the one that gets you unstuck. Whether that’s a tool, a service, a course, or a person — if it moves you forward fast, it’s worth it.

In my case, upgrading my course platform wasn’t the “cheapest” option. But it was the fastest. And that speed had value. It got me unstuck. It got the project off my to-do list. It freed up my mental energy to focus on other things. And it actually delivered the result I was trying to achieve in the first place.

For you that might be hiring a VA to handle customer service, upgrading to the platform that has the feature you need instead of trying to frankenstein things together, investing in mentorship like the Lounge or Email Badassery so you can make your marketing more profitable. 

At the end of the day, speed is a competitive advantage – we can see that playing out in real time in the AI industry right now, for better or worse. The faster you can move, the faster you can test, the faster you can learn, and the faster you can grow.

And every time you choose the slow, cheap option over the fast, effective option, you’re choosing to stay stuck a little bit longer.

The Framework: When to DIY vs. When to Pay Up

Okay, so how do you actually know when something is worth paying for versus doing yourself? Because I’m not saying you should throw money at every problem. That’s not smart either.

Here are some questions you can ask yourself when you’re evaluating these decisions in your business… and what I probably should have done when it came to my AI bot creation.

Question 1: Do I actually have the time and bandwidth to do this well right now?

Not “can I do this?” but “do I realistically have the time to do this well given everything else on my plate?”

Because here’s the thing: you might be perfectly capable of doing something. You might even be good at it. But if you’re a one-woman show running a business, there are always going to be more things you could do than you actually have time for.

In my case with the AI bots, I absolutely had the skills to build them myself. But did I have the bandwidth? Clearly not. Because months went by and it still wasn’t done.

If something keeps getting pushed to the bottom of your to-do list, that’s your answer. You don’t have the bandwidth. And pretending you do is just wasting time.

Question 2: How long will this realistically take me — and am I being honest about that?

Be honest here. And then double it. Because everything takes longer than you think it will.

I thought building the AI bots would take me a few hours. Maybe a weekend. It ended up taking months because I kept getting stuck, distracted, and deprioritizing it.

If I had been honest with myself about how long it would actually take — factoring in my actual available time, the learning curve of a new platform, the inevitable troubleshooting — I probably would have made a different decision from the start.

So when you’re evaluating whether to DIY something, don’t think about how long it would take in a perfect world where you have unlimited focus and zero interruptions. Think about how long it’s actually going to take in your world, with your schedule, and your competing priorities.

Question 3: What am I not doing while I’m stuck on this?

This is the opportunity cost question, and it’s a big one.

Every hour you spend trying to figure out how to build the thing yourself is an hour you’re not spending on revenue-generating activities. Every week that project sits unfinished is a week you’re not moving forward on something else to grow your business.

For me, every week I didn’t have those AI bots live was a week I wasn’t getting the benefit I was trying to create. But more importantly, it was a week I could have been creating new course content, working with clients, launching new offers, building partnerships, marketing myself more — all the things that actually move the needle.

What are you not doing while you’re stuck tinkering with the tool, or wrestling with the integration, or trying to teach yourself the skill? That’s the real cost.

Question 4: If I pay for this, how fast can I move on to what actually matters?

This is the question that changes everything. Because it flips the whole conversation from “what’s the cheapest option?” to “what’s the fastest way to get unstuck?”

When I finally upgraded my course platform, I had those AI bots live in minutes. Not weeks. Not months. Minutes.

And the value of that speed wasn’t just that the bots were finally launched. It was that I got my mental energy back. I got that item off my to-do list. I got to stop feeling guilty about it. And I got to refocus on other work.

Speed is a competitive advantage in business. The faster you can move, the faster you can test, learn, and grow. And every time you choose the slow, cheap option over the fast, effective option, you’re choosing to stay stuck a little bit longer.

The rule of thumb: If paying for it gets you back to revenue-generating activities faster, it’s probably worth it.

What This Looks Like in Practice

Let’s bring this back to the real world. Because I know some of you are sitting there thinking, “Okay, Jessica, I hear you. But what does this actually look like in my business?”

Here are some scenarios where paying up is probably the right move:

Hiring help. Paying a photographer, bookkeeper, or an ads manager isn’t a luxury. It’s leverage. They can do in a few hours what might take days or weeks to figure out. And they’ll probably do it better than you because it’s their zone of genius, not yours. Even if it’s not a highly-skilled position, just hiring someone to manage customer service, shipping, or uploading new products can be a huge help. Your time is worth more than what you’ll pay them, and you’ll get your life back.

Buying tools and software. If a tool saves you 5+ hours a month, it’s probably worth the cost. Run the numbers. If your time is worth $100/hour and the tool saves you 5 hours, that’s $500 in value. If the tool costs $50/month, that’s a no-brainer.

Investing in education. A $1,500 course that gets you unstuck in 30-90 days is way cheaper than staying stuck for 6 months. Because the real cost of staying stuck is the revenue you didn’t generate while you were spinning your wheels.

As I’ve mentioned, when it comes to my AI bot. I could have kept being stubborn thinking I was going to get it built on that other platform. And if I had made that decision, it probably wouldn’t be live right now. Instead, I upgraded, launched the bots in minutes, and moved on with my life.

Was it the cheapest option? No. But it was the fastest. And that speed had value.

It got the project off my to-do list. It freed up my mental energy. It delivered the result I was trying to achieve. And it let me get back to focusing on the things that actually grow my business.

That’s the energy we need to bring to every decision. Not “what’s the cheapest option,” but “what’s the fastest way to move forward?”

The Challenge

Alright, here’s your homework. And I actually want you to do this, not just nod along and forget about it the second this episode ends.

Step 1: Identify one thing you’ve been avoiding because you’re trying to “save money” by doing it yourself.

Maybe it’s hiring a VA. Maybe it’s upgrading to a better platform. Maybe it’s investing in a course or working with a coach. Maybe it’s paying for a service instead of trying to DIY it.

Step 2: Ask yourself, what is this delay actually costing me?

Not just in dollars, but in time, mental energy, momentum, and opportunity cost. Be honest. Write it down if you need to.

Step 3: Make a decision. This week.

Either commit to doing it yourself with a deadline — and I mean an actual, no-BS deadline that you’re going to hit — or invest in the solution and move on.

Because here’s the truth: your business doesn’t need you to be a martyr. It doesn’t need you to do everything yourself. It doesn’t need you to prove how scrappy you are by spending 20 hours to save $100.

Your business needs you to be strategic, fast, and focused on what actually matters.

So stop optimizing for pennies when you’re losing dollars. Stop getting in your own way. And go make some money instead.