How this business owner went from feeling “messy” to calm and in control of her personal finances
“I knew Cole as a friend and as a fellow entrepreneur, but I didn't know her as a financial professional. And I know she says she doesn’t judge, but getting on a call, and seeing that, and feeling that was really important. I could tell that she was completely there for me. She wasn’t prescriptive or judgy at all.
“And I saw the power of working through it one-on-one. She never said anything like, ‘here are the seven action items that I recommend to everyone.’ It was very tailored to my goals, and it was so personal — and that was really helpful.
“I don't feel afraid to open my bank account anymore. Seeing how Cole looks at money, having those conversations about money, and saying the numbers out loud with zero judgment — that's such a powerful habit.”
- Annie, B2B SaaS Copywriter
THE CHALLENGE
Annie was on top of her business finances — but felt disorganized when it came to her personal finances
Annie Bacher works independently as B2B SaaS Copywriter, helping tech teams connect with their audiences through human-sounding, empathetic copy.
And she’s awesome at her job. So naturally, when we first started working together near the end of 2021, her business was thriving.
“At the time, I had just gone through a period of growth in my business where I started taking myself seriously, I was earning a lot more money, and I had hired a bookkeeper,” Annie says.
“I felt like I really had my stuff together on the business side — everything was flowing, I had a system, I was paying myself a regular salary, and I just felt really on top of it.”
But that feeling didn’t extend to her personal finances.
“As soon as the money hit my personal account, all of that organization was just gone,” remembers Annie.
She had read a few personal finance books and laid some solid groundwork for herself — like setting up an investment account, a high yield savings account, and a retirement account.
“But even so, I felt kind of messy,” Annie says.
“I wasn't struggling financially. I was earning enough money. But I had no real idea how much I was spending every month. And I was saving sometimes, but it was haphazard.”
“In previous years in my business, money was coming in and I didn't really have a way to know where it was going. But now that I had a clearer picture, I could see that I was earning this money, and that it was enough to save and invest. I just needed to be more responsible about how I went about doing that.”
Annie loves reflection and goal setting, so with this clearer picture of her business finances in mind, she decided that her big goal for 2022 would be to build up $10,000 in her personal emergency fund (which she prefers to call an abundance fund — because words matter!).
So she had a concrete savings goal — but she didn't yet have a plan for how to reach it.
With everything so clearly systematized in her business, she was starting to feel more ready to create systems for her personal finances as well.
“I was more on top of my finances than I thought, but I just did not feel on top of it, because there was no system,” she says.
And at first, she wasn’t sure how to start creating that system. Partly because her situation was so unique. Annie is originally from the United States, but lives in Buenos Aires, Argentina. That means she has bank accounts in two different countries, operates in a lot of cash, and does most of her spending in a currency that regularly fluctuates in value.
“I had kind of convinced myself that my financial situation was too complicated, that nobody would understand, and that no typical financial advisor or budgeting software could help.”
“I felt like I definitely wouldn't want anyone looking at my personal finances, because it was kind of a mess, and I was sure I was doing things wrong,” Annie explains.
Annie echoed something I hear from my clients all the time, saying, “I felt like everyone else has it together, and I don’t.”
“People don't talk about how everyone struggles, how everyone feels like their finances aren't up to snuff — and I don't think I realized that,” she says.
And although she’d appreciated having a bookkeeper looking at her business finances, she felt a little hesitant to hire someone to look at her personal accounts.
At the time, Annie and I knew each other from college, and crossed paths again in an online community of alumni entrepreneurs. Eventually we connected and set up a services swap (Annie helped me with copywriting, and I helped her with personal finance).
So, I suggested she start where I start with all my clients: a Spending Staredown.
“Looking back, I was fine — but I didn't feel good about my finances. And that was giving me a low level of stress. I would think, ‘Oh, I really should handle that. But I have no idea where to start.”
“I was more on top of my finances than I thought, but I just did not feel on top of it, because there was no system… I would think, ‘Oh, I really should handle that. But I have no idea where to start.’ I felt like I definitely wouldn’t want anyone looking at my personal finances, because it was kind of a mess, and I was sure I was doing things wrong.”
THE PROCESS
Annie looked at her money without judgment, so she could start building habits and systems that work for her
“At first I didn’t really think I needed a Spending Staredown,” Annie says, “because I didn't feel like my issue was spending — I felt like it was everything else.”
“I thought she was going to give me homework to track my spending. But instead, Cole asked me to open up all of my accounts and read off all of my expenses from the past month, so she could write them all down right there, live on the call,” remembers Annie. “And I was like… what?”
At first she felt a little resistant, saying there wasn’t enough time, and that it would be too complicated with her operating in two currencies and in a lot of cash. I let her know we had plenty of time, and we could just pick an exchange rate and run with it. Despite the discomfort she was feeling, Annie decided to give it a try.
But after just an hour of looking at her money, Annie completely flipped her perspective on what it meant to track her spending.
“And then we did it. We went through, and I read out every single expense,” Annie remembers.
As she read off her expenses, I wrote them down in a shared spreadsheet, and organized them into different categories, like baseline expenses, food, travel, etc.
We also created some Annie-specific categories to represent her priorities, like sports. Annie is a badass runner (she’s run 6 marathons — six!!), which means she has regular running-related expenses.
“And that was really helpful too,” says Annie, “Because instead of saying, ‘oh, no, I spend so much on running things,’ we just made that a category, and gave it a column in the spreadsheet.”
“Cole made it really clear that she was not judging my purchases, that we were literally just getting it down on paper so that I could look at it,” says Annie.
“That was really cool. Because that was the first time I had ever had anyone in my personal finances, and Cole wasn't just saying that she wasn’t judging me — she was actually not judging at all, which was really nice.”
“And on top of just being really nice, when Cole looked at my money without judging me, she modeled how I could look at my money without judging myself,” Annie says.
Annie explains that the process of looking at her spending without judgment — beyond just feeling better — has a practical impact.
“If you're judging yourself for your spending or for how you're managing your money, then you get stuck and you can't move forward. And that's just not very productive,” she says.
"I realized I could really benefit from making this more of a habit, so I decided to do the full 6-Pack of Staredowns. I know I do really well with accountability. So, knowing that I was going to be seeing Cole every month meant that it was more likely I’d actually do the action items we defined together,” Annie says.
Once we had that number, we were able to tackle her questions and goals one at a time, which meant doing some simple math to figure out…
How to make a plan to reach $10,000 in her abundance fund, so that she feels covered in case of emergencies or unexpected circumstances
How much to contribute monthly to a life events fund, which she can draw from down the line for things like a wedding, or a house, or whatever she decides to do next
How much to contribute monthly to her investment account, so she can passively build wealth in an index fund
How much to contribute monthly to a retirement fund, so she can have plenty to fall back on when she’s ready to stop working
We met once a month for the following 6 months, and over time, we were able to calculate her average monthly spending — the number that Annie needed to create the systems she was missing.
“I really liked how everything that Cole does is simple,” says Annie. “I thought personal financial spreadsheets would have all these complicated formulas, and that it would just be too much. But all we needed were sums and averages — and it was all very easy to understand.”
In addition to our simple, shared spreadsheet, it was a huge help that the systems Annie had set up in her business were so crystal clear and organized. This made it easy to see that she could be paying herself a higher salary — and then contributing more to her savings and wealth-building goals.
“I used to be hesitant to pay too much of my business earnings into my personal account, because I was afraid I’d spend it irresponsibly. So I hoarded money in my business account, where it wasn’t really doing much work,” she explains.
“Because of Cole’s help to figure out my monthly numbers and understand how to actually distribute my earnings into savings, investments, and retirement funds, I started slowly increasing my salary for my business — because I started to see how to distribute that extra cash responsibly into these different accounts.”
Once we got clear on the amounts she could start contributing, Annie got to work setting up recurring transfers to all of her accounts.
“Cole encouraged me to start small and just get in the habit. So I set up $100 a month to each account. And then as we kept working together, I realized I had room to pay myself more and increase those transfers,” Annie explains.
“And Cole got out her calculator and showed me how much faster those savings would grow the more I saved each month, which was motivating — super simple, but helpful.”
With those transfers all set up and running smoothly in the background, she started working towards her savings and wealth-building goals every month, automatically.
After 6 months of Staredowns, Annie was feeling like she had enough systems and clarity in place to switch to Quarterly Calls. This meant getting together once every 3 months to check in about her spending, her net worth, and her goals, and anything else that came up for her.
“I knew Cole as a friend and as a fellow entrepreneur, but I didn't know her as a financial professional. And I know she says she doesn’t judge, but getting on a call, and seeing that, and feeling that was really important. I could tell that she was completely there for me. She wasn’t prescriptive or judgy at all,” Annie remembers.
“And I saw the power of working through it one-on-one. She never said anything like, ‘here are the seven action items that I recommend to everyone.’ It was very tailored to my goals, and it was so personal — and that was really helpful.”
“I found it really helpful to just note it down every time I'd have random financial questions, and then be able to bounce ideas off Cole every time we talked,” says Annie.
“When Cole looked at my money without judging me, she modeled how I could look at my money without judging myself.”
THE RESULTS
Annie doubled her salary and her savings, and built systems that help her feel calm and free
Over the course of working together for a year and a half, Annie consistently took action on all the goals and to-do’s we defined in our calls — and ultimately she was able to…
Hit her goal of $10,000 in emergency savings before 2022 was over
2x her salary
2x her savings
Set up recurring transfers to all of her savings and investment accounts
Let go of any judgment she felt towards her spending, and stop feeling afraid to open her bank accounts
Over time, as Annie figured out what systems worked for her, she felt more confident raising her salary, and moved more and more cash from her business account to her personal account.
“I started paying myself more than double, and almost all of that went towards savings, investments, retirement, and things that are important to me, like recurring donations to causes I care about.”
She’d started small with her recurring transfers, but now she’s steadily contributing…
$500 a month to Life Events
$500 a month to Abundance
$500 a month to Investments
$500 a month to Retirement
And, $100 a month to Travel! This is a new one that Annie is excited to increase in the future, so she can proactively save for trips and stop feeling guilty about spending “too much” on travel.
“After a year of working with Cole, my savings doubled,” says Annie. “And I wasn’t earning significantly more in my business – I had just learned to manage my money in a more systematic, proactive way.”
“I really care about the power of habits compounding over time. It was clear that Cole could help me develop these habits and get accountability around setting up systems. And then all of that compounds, not just over the months that we're working together, but over my lifetime,” she explains. “Even if I don't spend any time outside of our calls, even just those hours on Zoom could be huge financially — just because of how investing works and how taking little actions can make a big difference.”
“That was part of the calculation in my head of, ‘is this worth it?’” Annie says. “I thought, ‘well, if I can just do these little things, it’ll pay off.’ And it absolutely has, and I know it will continue to pay off moving forward.”
“I now have habits that will serve me exponentially over the years to come. I have automatic recurring transfers to my savings and investment accounts, and goals for a giving plan.”
And the best part? Getting there was a lot easier than she thought it would be.
Annie says that in the end, investing in financial planning support was worth it.
Annie reached those goals by building the habit of looking at her money without judgment — and then pairing that with tangible, low-effort action steps.
“I don't feel afraid to open my bank account anymore. Seeing how Cole looks at money, having those conversations about money, and saying the numbers out loud with zero judgment — that's such a powerful habit.”
“It’s so simple, but this work with Cole has changed my life. In terms of systems, just knowing that those transfers are working in the background, feeling like I know what I'm doing, and knowing I have things under control means that I have more freedom to make the financial choices I want to without second-guessing myself.”
For instance, Annie lives in Argentina, but her whole family still lives in the US — so travel is a big priority for her.
“It’s really important to me to be able to travel to the US and go to the weddings, go to the graduations, and just be there for my family,” she says. “I don’t want to have to think, ‘Wait, can I afford it? Is this worth it?’ I want to always say yes if it's like a family thing.”
Annie loves being generous with her friends, too. Recently, she decided to book a riverside AirBnB for her and some close friends to hang out in for a long weekend — because her friends were moving away, and she wanted to have one big weekend getaway together before being far apart.
“Being able to do that and not question whether or not I should be spending that money was really cool. Having all my financial systems together made that not an issue.”
“In the end, it really wasn't that complicated,” says Annie. “I hit my ambitious goals without feeling like it took too much effort.”
“It felt like, I know I can do this because I know how much I spend. I know I have all these backup savings. I have this abundance fund. I'm covered, so I can be generous to other people.”
“And now I have this amazing memory of all of us spending three days together on a river, just drinking maté and chatting,” remembers Annie.
“The more secure we can feel in our financial situation, the more we can help others and be generous — whether that means spoiling your friends or donating to causes and organizations.”
Looking to the future, Annie is excited to set up even more systems that make giving feel easy.
“One of my 2023 goals is creating a giving plan. Cole helped me figure out the first step — auditing all of my donations over the past year. Once I know that number, I can put together an organized plan instead of donating randomly,” says Annie.
“Because if you feel like you're just giving money randomly, and you have no idea how much you're actually spending, then you're less likely to give. But if you know exactly how much you’ve allotted for this — if it’s just a part of your budget for the year — then it's easy to be generous.”
Right now, Annie feels like she has enough systems and habits in place to manage her personal finances on her own moving forward.
“I feel good about where I’m at in my personal finances, and nothing major is changing in my life at the moment. But it’s really nice to know that if something does change (say, I decide I want to make a big investment in a house or something else major), I can reach out to Cole and trust her to help me navigate that.”
And I’ll be here whenever she’s ready. Go, Annie, go!
“It’s so simple, but this work with Cole has changed my life. In terms of systems, just knowing that those transfers are working in the background, feeling like I know what I'm doing, and knowing I have things under control means that I have more freedom to make the financial choices I want to without second-guessing myself.”
“The more secure we can feel in our financial situation, the more we can help others and be generous, whether that means spoiling your friends or donating to causes and organizations.”
Build habits and systems that that will serve you for years to come
Reach out to learn more about how we can get you feeling calm and in control of your personal finances.
