Hi, Reader!
This week's newsletter is one we've never done before: Reader Q+A.
I chose 3 reader submitted questions that weren't topics I've really expanded on over on Instagram and I'm going to dive into them here.
- How do you get over the fear of failure in budgeting?
- What the heck does Kyle do for work!? (Totally valid questions coming fresh off the heels of a trip to Mexico and Disneyland ๐คญ)
- Are my kids involved in budgeting and modeling financial practices to them?
"How do you get past the fear of feeling like a failure and get started? It feels so overwhelming?" -Katy
When it comes to money and failure, the stakes are high for a few reasons. The first one I really don't like but it doesn't make it real: money (or the appearance of having money) is unfortunately one of our society's main status measurements.
We don't get to keep our financial life completely a secret: people see the car we drive, the home we live in, the activities our children do or do not do, the size and frequency of the trips we take, the clothes we wear, and on and on.
Unfortunately, we also have access to tools (mainly debt) that allow us to have the appearance of money without actually having it. So we are tempted to allow others to believe we have money when really what they see is just a list of our debts disguised as accomplishments.
Another reason the stakes are high: a financial error can impact us for years and years to come even if the choice was made in a moment.
So how do we acknowledge these high stakes without letting them paralyze us?
I'm not an expert or a counselor but I'll tell you what I learned and what has worked for me: Asking myself questions about the deeper reason for my fears and allowing myself time to find the answers.
First, I learned about debt. And the negative impacts of it. And the hidden nature of it. I learned about compound interest and the true cost of a purchase if we make payments on it.
And I asked myself: "Is that actually what I want to do with my money every month for the next 5 years?"
Another question I ask myself regularly: What happens if I do nothing?
If you struggle with a fear of failure, it can be so easy to believe that staying still, not making any decisions, and certainly not making any changes will keep you safe.
But when it comes to money, choosing to do nothing actually has negative consequences.
For example, if I recognize that in order to pay off my credit card balance every month, I have to pull money from my savings: what are my options?
Option A: set a budget that fits into my income, adjust a few spending habits, and stop seeing every transaction as unavoidable.
Option B: panic and commit to not buying anything. Realistic? No. But it could stop the bleeding for a month or 2.
Option C: do nothing because both of those options are overwhelming.
See the problem? If we choose Option C, we actually choose for our savings to continue to shrink. We do not solve the problem we simply delay it. And when we are forced to deal with it down the road, it will in fact be worse than it is today.
So I suggest writing your options down. Get specific with concrete ways you could respond to your fear and what the long term implications of each response would be. This can start to reduce the anxiety around change and the false belief that doing nothing is safe.
No one is doing it well - we are all failing
I think one of the main roots of a fear of failure is the belief that we will be alone in that failure if it happens. That if we mess up, it will be a unique mess.
It will not be.
Your debt, your lack of a budget, your spending you keep secret from your spouse, your celebration of stuff without caring how that stuff was acquired.... they are tales as old as time.
They are easy for me to rattle off because of how frequently I encounter them.
You are not alone. In where you are right now, in the attempts you're making to budget and figure this crazy thing called personal finances out, or in your failures while you learn.
The only way to make failure less frequent is to START.
Everyone fails. But no one fails all the time. Experience, mistakes, lessons, mentors, resources, and good old sweat equity do eventually work.
You WILL get better the more you try. Whether it's trying a new budget, a meal plan, a weekly meeting with your spouse, taking your kids on outings. It will feel awkward and there will be errors in the beginning because that's what the beginning is for.
But it won't stay that way.
When you fail - because you will.
I've talked on instagram a lot about my former fear of flying. I still don't love it, but I don't have a panic attack on every flight anymore. One of the main reasons for this is that Kyle and I lived with a couple for 5 months during an internship and the husband was a commercial pilot.
I told him about my fear of flying and he said "tell me exactly what you're afraid of." I expressed the feeling that flying was different from driving in that there are 1000s of things that can go wrong while driving that won't kill me, but flying doesn't have room for error since you're in a giant tin can hurling through the air 30,000 feet up.
He laughed. Because of his experience, training, and knowledge, he knew that not only are mistakes, errors, and "failures" not fatal in flying, but he is so well trained on them that they don't even increase his heart rate.
Planning out how you will handle failure is a much better use of your time than attempting to avoid it all together. That's why I believe in emergency funds so much: they allow you to fail!
Change your goal to: persistence. This is a goal you can succeed in because it means that no matter how bad the mess up is, no matter how many months you go without looking at your budget, "success" is always in front of you by beginning. And beginning again.
"What does your husband do for his new job?" -Lisa
Some of you were around long before Kyle had this job, but many of you were not so here's a brief history of how we got here!
2013: Graduated college with a degree in Youth Ministry and Preaching
โ2014: Finished a youth ministry internship and got hired as a Regional Director at the Christian Summer Day Camp where we'd both worked in high school.
โ2018: Became the Executive Director at camp. Because it was such a small organization (only 4-5 full time staff), he was responsible for marketing, donor relationships, website, programing, and the finances.
โ2022: He felt the pull to leave this job. It was extremely physically taxing, low pay, and busy hours that were opposite of our kids' schedules as they got into school. He finished the summer and left in September to help me grow Debt Free Mom and do some freelance website design and marketing work.
โFeb. 2024: Debt Free Mom had a major dip in revenue (spring is always low season but this felt really low) and the cost of many things were rising. Being the worrier I am, I was very concerned about getting out in front of the dip in income so as to not have long term consequences so he started applying for full time jobs.
โMay 2024: Kyle's brother worked at a marketing agency who exclusively served non-profit agencies. He asked Kyle if he'd be interested in some freelance work which he was eager to do. He had a few conversations with the person looking for freelance work then was asked "actually do you want to apply for a job?"โ
He went through several interviews (his brother was awesome in getting connected and also awesome in completely staying out of the process so that Kyle could succeed or fail on his own merits alone).
โJune 2024: We were on vacation with Kyle's family and he did 2 interviews tucked away in a bedroom of the beach house. He got offered the job a week after we came home and started right after 4th of July.
So what does he actually do?
He was hired in July 2024 as a Digital Strategist - writing copy and planning marketing campaigns for digital fundraising efforts for a roster of clients whom he serves along a team of other people in the company.
In October 2025, he was promoted to Account Lead. This means that while he is still on a team of people who service their own roster of clients, a few of the clients are specifically assigned to him as their main contact as well as now having a direct report (a part of his job at camp that he loved and missed! He is an excellent leader of people.)
Basically he writes and writes and writes any time he's not on a meeting. He works from home, but travels regularly to the company headquarters, conferences to attend or speak, and visit clients in person.
This has been a dream of all dreams for our family. Everything he did at camp for 10 years led to this job - it prepared him to understand deeply the goals and frustrations of non-profit organizations, to know the nuances of marketing that isn't directed at sales but instead at donations, and to work well in teams for a common goal. This job allows him more flexibility than I thought possible in a full time private sector position while also paying more than we dreamed would be possible coming off a decade of establishing and growing our family on a non-profit ministry salary.
He loves his work. Just last night, he spent hours on a Saturday working on something he had learned about at the most recent conference he attended - because he wanted to. No deadline, no boss expecting this of him, just a passion for the work.
I can't wait to see how he continues to grow. He went into the job feeling inadequate but determined. He knew he hadn't done a lot of the technical work, but he also knew he's a researcher (enneagram 5: if there's anything he isn't an expert in, it's simply because he doesn't want to be. If he's interested, he's not satisfied until he knows everything about it. I love this about him).
I remember him getting to the end of the day when he first started the job and telling me all the things he had to google in order to do them. Now? He knows what he's doing, truly. And he knows how to find the answer when he doesn't.
TL;DR: he writes emails and paid advertisements for large non-profits to support their organizations through digital fundraising. And has a lot of fun doing it because the company is FUN.
"Have you started involving your kids in your family budget? How have you worked with them on teaching money concepts? Was thinking about how you are working on modeling more house maintenance and curious about financial teaching." -Lauren
Short answer: they're not involved in our family budget, but they know what a budget is.
Teacher talk: they are currently learning the pre-requisite skills needed for budgeting.
I say regularly: "Dad and I make a budget which helps us plan how we want to spend our money and that's not in the plan right now."
Telling children that something costs too much money is NOT a bad thing: because it's the truth.
Shielding children from something that is both true and a part of their lives forever will not prepare them to face the world confidently.
I'm very passionate about this. ๐ Money is finite for everyone and teaching kids this truth is a kindness, not a disservice.
I want my kids to know that hard work (a paycheck) and planning (a budget) are the two main components of financial success. We often emphasize one to the detriment of the other.
Get money for Christmas, mow some lawns, get a good degree, go into a high paying field. But how much time do we spend teaching them to say "not right now" to themselves or planning out how they'll spend their $20 of birthday money in advance that balances short term and long term goals?
So I don't specifically show them our family budget. But I have these building block conversations regularly. They know that mom and dad work hard and are paid for this work. They know that when we say yes to one thing, it means saying no to other things. They also know that "not yet" is not the same as "never".
Their star rewards on our Skylight calendar are a form of a budget. They earn a currency in exchange for work and there are purchase options at a variety of price points that they can choose to get the low priced rewards frequently or delay their gratification in order to afford the larger (often more appealing) rewards! One of the rewards available to them is to exchange 50 stars for $5 cash.
Lastly, secret and private aren't the same thing. It's not a secret that we budget and that we say no to ourselves and to them in order to achieve our larger goals. But we currently choose to keep our budget private in that I don't want them to know how much we make or how much we spend. Kids latch on to these larger than life numbers while missing the big picture principles, so I share the habits and values without the numbers.
As with all parenting topics, there are many good ways to achieve the goal of raising financially wise children, this is just how we are doing it for now!
PHEW! That was a lot longer than I expected it to be. If you made it this far, I would give you 30 stars on your Skylight profile which is worth 30 extra minutes of video game time or you can save them and when you get to 50, cash them in for $5.
PS: Looking for something specific from me? You can probably find it here!โ