I’ve only been in debt for about 28 years.

Considering I’m almost 46 that’s kind of a long time.

Ever since I could make money, I spent beyond my means. As a hard worker, I could never really understand why I was constantly behind on bills; I should have been rolling in it.

I’ve had many close calls when it comes to being broke but then something crazy happens; a refund check from the dentist would show up, an early birthday check from my dad, a long-lost insurance reimbursement. I have the Universe to thank for my life just always ‘working out’. Don’t get me wrong, I love it that way, but it’s risky.

AND, I’ve had enough almost-rock-bottoms to know that when it manifests physically in my body or infiltrates in to my relationships, I know it’s time to pay attention. This is exactly how I got sober; it wasn’t rock bottom but I skipped along it for a while.

And so, now I’m here on Day 1 of a Debt Diary. Let’s get mighty real here because being totally honest is really the only way I know how to bring the monster out from under the bed. That monster for me, and probably most of us with self-medicating and/or money issues, is shame. There’s no doubt I have made money mistakes to get me to where I am today however, that IS what they are. Mistakes.

Mis-takes. We get re-takes.

I am going to share all the numbers and my plan but first I’ll give you a little history.

I am the daughter of a financial planner. In my dad’s defense, he tried to teach me all the right ways to spend and save with all of his yellow legal pads, four of the same sentences he said over and over (that I mostly rolled my eyes at), a demonstration of compound interest, the percentages of each paycheck that should be going to savings, bills, housing and investments, etc. He also led by example and can do all the things he wants because he is truly financially free.

I thought I knew better than him.

I didn’t.

As soon as I could (at 17) I moved in to my first apartment with a friend working two jobs and still ended up not being able to cover rent. I got behind, had to crawl to daddy to bail me out of a $740 back rent issue and basically lost a friendship over spending more than I made. Fast forward a few years and I left for Army National Guard Basic training where I left my mom with all my bills and a plea to help me pay off $5000 worth of credit card debt and a real-bad vacuum purchase. I came home and married the man of my dreams who had $20k in the bank and promised me a wrap-around porch. I thought all my money woes were gone…somebody to save and take care of me. Yay.

Wrong.

Our newly-wedded bliss was sprinkled with the excitement of entrepreneurship and big commission checks only to be tainted by a $30k IRS tax bill we didn’t save for and $20k worth of credit card debt that bought what-I-don’t-know. (This was another one of those yellow legal pad lessons I ignored: save 30% for taxes when you’re self-employed. Whoops.) We had to crawl to my in-laws this time and graciously they bailed us out. And then, we bought a house high and took a bath on it in 2008. This time my in-laws bailed us out again by letting us live in their basement for two and a half years with our 6-week old son until that house sold for $30k less than we bought it for. But Dale had a good job and we had few bills so I thought we could get ahead a little.

Not so much.

(Geez. This is difficult to write out. I’m starting to sweat.)

We finally sold our house, moved in to a modest ranch, put some sweat equity in to it and then did a big remodel borrowing the money for that from my mom. When we sold that house we were able to pay her back and put a down payment on a new house (with a porch). We were pretty stretched but not enough to start paying attention.

It was fine.

Within five years we started a wine bar business which included purchasing a commercial building. The fact that I had the balls to even go to the bank made me pretty proud. The business actually made quite a profit during the pandemic and spending was fun so we bought a coffeeshop business. Both of those things fueled my confidence in business ownership enough to open an ice cream shop/candy store, purchase another commercial building and quit my real job. My husband left his real job and we both became 100% self-employed overnight.

The thing that no one tells you about a service based business like a bar, coffeeshop or ice cream store is that over everything else: staffing, rent, cash flow, product, inventory, customers, all of it, the number one energy and money suck are appliances. Freezers, coolers, blenders, panini makers, beer tappers, dipping coolers, microwaves, soup kettles. And the dishwashers. The fucking dishwashers. In less than 4 years I paid over $20k for new dishwashers.

Guess where all of those purchases went?

Right on to shiny, pretty, platinum-plastic credit cards. And because revenue was high and the construction market was great, I thought we deserved a retreat and I convinced us a little cabin 30 minutes from our house would be another successful business venture (AirBnB). So we tied up a significant amount of cash for the down payment and committed to another monthly payment.

Then we sold a business, got a nice chunk of change and instead of saving it or paying down our debt, we sunk it in to another expansion and remodel. I actually think this was one of our better business/financial decisions and we’ve already seen the fruits of that labor, however, it left us very, very house rich and cash poor. And with inflation at 18% over 3 years, our cash flow stopped flowing.

Cue: construction market slow-down because of the interest rates.

Ironically, my 2024 resolution was to pay attention to our finances. I don’t know if this coming-to-Jesus is because I opened my eyes and it’s been this bad before when I had my head in the sand or it just happened to get this bad while I was watching. Either way, I am actually grateful it worked out the way it did.

About a month ago, I could see in my husband’s eyes that he was scared. He came in to the bedroom and he looked so sad and defeated I actually said out loud, “Do you want me to be worried?” And he said, “I think it’s time.”

Even as I write this I just sighed really loud.

It was the wake up call I needed. I knew I would need a plan of action so I followed the steps below:

  1. Called my sister and showed her all of my finances. Everything. I had avoided her help for fear of judgement for too long. She’s been through this, on a smaller scale, but understands the behavior changes that are needed. And she loves me so she just wants me to be happy. I know that now.
  2. I wrote down every single thing we owe and since January I have been tracking our spending habits so May will begin a new spending plan (aka budget)
  3. We had a serious conversation and decided selling the cabin was the wisest decision for us. We hope to get around $35k back after all taxes and closing costs.
  4. I closed out my 401k and a $20k is on the way.
  5. We toyed with the idea of asking a parent for another loan to get out from under the extremely high interest rates of the credit cards but in the end, I NEED to do this on my own. Getting bailed out, even if it will save us money or is deemed the “smart” thing to do by society standards, will not solve this issue. I have 14 paragraphs of proof above here. I had to beg my husband to trust me to do this. That was hard. Staying in debt is harder.
  6. I started taking intentional action; from the littlest things to the more aggressive. I saw a penny on the floor of our cabin that was just about to be picked up by the Roomba. I stopped it, picked it up and put it on my phone so I could take it home. I took the change cup from my desk and traded it in for bills: $42 that has just been sitting there on my desk. I folded it neatly and in order and put it in my wallet. I started this journal in hopes that putting it out to the world wide web will bring the accountability I need to keep going. We cleaned the cabin, made some repairs and brought personal items home in preparation for listing it this week.
  7. I reframed my mindset around self-care. Financial security is one of the values I have been waiting for from someone else almost my entire life. I don’t need to be saved. I’ll be doing the rescuing myself from now on.

Here are the big picture steps you can use to customize your own plan:

  1. Continue Open Communication: Maintain open and honest conversations with your support system about your finances. Their support and understanding can be invaluable.
  2. Consolidate Your Debts: Consider consolidating your high-interest debts into a lower-interest loan if possible. This can make repayment more manageable and save money on interest over time. Beware that this is not a “bail-out”.
  3. Create a Detailed Spending Plan: Utilize the information you’ve gathered from tracking your spending (start tracking now) to create a comprehensive plan until your debt is paid off. Allocate funds for essential expenses and prioritize debt repayment.
  4. Utilize Windfall Funds Wisely: If you come in to a big chuck of change, use it wisely.
  5. Avoid Further Borrowing: Resist the temptation to seek additional loans, even from family members, to address your debt. Focus on managing your existing debt responsibly and developing healthy financial habits.
  6. Embrace Small Wins: Celebrate small victories along the way, such as finding spare change or converting it into bills. Every effort counts towards your goal of financial freedom.
  7. Stay Accountable: Journal your progress and share your journey with others for added accountability and support. Consider joining online communities or support groups focused on debt repayment for additional encouragement.
  8. Prioritize Self-Care: Remember to prioritize self-care throughout this process. Recognize that financial security is a personal responsibility, and empower yourself to take control of your financial future.
  9. Seek Professional Guidance: Consider consulting with a financial advisor or debt counselor for personalized guidance and strategies tailored to your specific situation. They can offer expert advice and help you develop a realistic plan for achieving your financial goals.

By following these steps and remaining committed to your goal, you can gradually work towards becoming debt-free and achieving greater financial stability. Keep believing in yourself and the progress you’ve already made. You’ve got this!

If you’ve made it this far, you’re probably interested in the down and dirty numbers huh? Stay tuned for Day 2.

Setting boundaries is hard, but necessary for any kind of success.

This week I had to say no to a friend.

One of my dreams is to start taking clients on self-care retreats to amazing destinations coupled with some lifestyle design, delicious food, adventurous excursions and good company. I share this dream with one of the most empowering, soul-led business-owning women I have the honor to know and this week we had a plan to meet (in-person) to start the process.

Starting last week, I had a nagging feeling in my gut (ah, that’s intuition for those of you that don’t know it originates in your stomach) that I shouldn’t go. The boys were just getting home from Patagonia after a week on Spring Break, my son started the spring golf season (for the first time), I had meetings I would have had to rush to get back to and following my surgery two months ago, I finally turned a healing corner where I felt I could get back in to a routine. It was overwhelming.

For three full days I struggled with listening to and caring for myself versus disappointing Cindy. I’ll be honest here, and this is embarrassing, I thought of many lies I could have told her that would have ‘forgiven’ me; illness that would have let me off the hook. But what kind of self-care coach would I be if I did that? A hypocrytical one for sure, but it also just didn’t feel right. I have enough respect for myself and Cindy to be honest and let her know I was feeling overwhelmed. It wasn’t that the retreat dream isn’t a priority, it’s just lower on the list than my family and my own wellbeing right now.

I texted her the following:

I am feeling really overwhelmed right now. The boys are not getting home until later today from Patagonia, Miles starts golf tomorrow after school, I am short staffed at Crossroads (my manager’s dad is old and ill) and Dale is working late every day this week to catch up from last week. ‍♀️ However, this retreat planning trip is extremely important to me. Help me.

Her response came a few hours later. Had I lied I to her, I would have been checking my phone incessantly to see her response, but instead, I put my phone down, took a deep breath and felt freedom. Of course, because we respect one another, all is right in the world and we are making the meeting work through this beautiful thing called technology.

This is the hard shit.

The stuff that you have to wrestle with for a while, sit with the feelings of someone else (maybe) being disappointed, letting someone else down but in turn making yourself a priority. We have to start respecting ourselves MORE than we respect others.

What if, instead of automatically agreeing to every request that comes our way, we start prioritizing ourselves and our needs? What if saying “no” becomes an act of self-care rather than people-pleasing?

Here’s the thing: saying “no” doesn’t make you selfish or uncaring. It’s about setting boundaries and recognizing your limitations. It’s about honoring your time, energy, and mental health. And guess what? It’s perfectly okay to do so.

So, how do we master the art of saying “no” without feeling guilty or rude?

Here are a few tips:

  1. Know Your Priorities: Before committing to anything, take a moment to consider your priorities. What truly matters to you? What do you need to accomplish? By understanding your priorities, it becomes easier to decline things that don’t align with them.

  2. Practice Self-Awareness: Tune in to your own feelings and needs. If saying “yes” to something feels draining or overwhelming, listen to that inner voice telling you it’s okay to decline. Trust yourself and your instincts.

  3. Set Boundaries: Boundaries are your best friend when it comes to self-care. Learn to say no firmly but kindly when something doesn’t work for you. Remember, you’re not obligated to explain or justify your decision.

  4. Be Honest: Honesty is key in any relationship, including the one you have with yourself. If you’re declining an invitation or a request, be honest about your reasons. Most people will respect your honesty and understanding.

  5. Practice Self-Compassion: Saying “no” may feel uncomfortable at first, especially if you’re used to always saying “yes.” Be gentle with yourself and remember that prioritizing your well-being is not only acceptable but necessary.

  6. Offer Alternatives: If you’re declining an invitation, offer alternatives if possible. This shows that you value the relationship and are willing to find alternative ways to connect or contribute.

Remember, saying “no” is not about shutting people out or being dismissive. It’s about valuing yourself enough to prioritize your own needs. By learning to say “no” for self-care reasons, you’re not only taking care of yourself but also setting a powerful example for others. So go ahead, embrace the art of saying “no” and watch how it transforms your life for the better. You deserve it!

And the circle we don’t talk about.

The closest people in your life are not {necessarily} going to be your best customers.

I thought when I opened my first business I was going to be guaranteed at LEAST 100 customers because we have a huge family and a large circle of really great friends.  You can imagine how broken-hearted I was when I could count on one hand how many of them walked through the door after the initial grand opening with free champagne stopped flowing.  I thought I had failed.  I thought they didn’t support me.  I thought and thought and thought and thought.

And that got me no where.

Initially, wrapping my head around this social circle concept as it pertains to business ownership was tough. But I’ve developed a philosophy over the past few years that’s been a lifesaver for my tender heart—it’s what I call my “FIRST CIRCLE, SECOND CIRCLE” theory.

FIRST CIRCLE

The first social circle comprises those closest to you: your partner, parents, lifelong friends, maybe your closest pals, or even siblings—those who’d go to the ends of the earth for you (maybe not that dramatic, but you catch my drift). These are the folks who love you unconditionally and would do anything to shield you from harm. It’s a tight-knit, inner circle. However, they’re not going to be your best customers. They may never visit your business, buy a product, suggest your services to friends or even mention or ask about your dream. This is confusing and hurtful because isn’t this the circle you should be able to count on the most?

SECOND SOCIAL CIRCLE

Then, there’s the second circle. It’s broader, encompassing acquaintances, friends of friends, beloved relatives, your parents’ or siblings’ buddies, social media connections, customers, clients, community members, former colleagues, neighbors, business allies, fellow female entrepreneurs, and anyone genuinely rooting for your success. These are the ones that suggest, share and buy from you BECAUSE it’s you.

social circle

Here’s the crux: your first social circle keeps you grounded, reminding you of life beyond the business world. They offer a respite from profit margins and strategic plans. Sometimes, it may seem like they’re not fully behind your dreams, but it’s out of concern, not lack of love. They’re the ones asking the tough questions, expressing doubts, maybe making snide remarks (which could be jealousy-induced, but that’s a story for another day).

Now, your second circle—hold onto these folks tightly. They’re your lifelines, your cheerleaders, your virtual and real-world support squad. You might not know them well beyond their Instagram handles, but they’re there for you. They understand the entrepreneurial journey, the fears of both failure and success, the loneliness of self-employment, and the importance of community support.

THIRD RING

Then there’s the third ring, often overlooked. It’s beyond the second circle and fades as you gain confidence and embrace authenticity. Initially, it’s glaring and irritating—the jealous, envious bunch. They wish they had your courage and determination but lack the guts. They can be noisy, but remember, their negativity stems from their own insecurities. It’s tough, especially in the beginning, but redirect your energy away from them. The less you engage, the quicker they fade into the background.

“At first they’ll ask you why you’re doing it. Later they’ll ask how you did it.”

Individuals may transition between these circles, perhaps moving from the third ring to the second once they witness your success. Some may even straddle both the first and second rings when they are assured of your safety, evolving into cherished customers and supporters. Embrace this fluidity as it’s a natural part of human nature. Holding ring-jumping against someone is a waste of your precious energy.

Understanding the dynamics of the “FIRST CIRCLE, SECOND CIRCLE” theory can be pivotal for navigating the journey of entrepreneurship. While the first circle provides grounding and protection, often questioning your decisions out of love, the second circle offers vital support and understanding, essential for fueling your ambitions. As for the third ring, acknowledging the presence of jealousy and negativity with compassion is crucial, but it’s equally important to minimize their influence on your path to success. By embracing the strengths of each circle and leveraging their respective roles, entrepreneurs can find balance, resilience, and ultimately, fulfillment in their endeavors.

What do you think? Does this make sense in your entrepreneurial journey?

“Make sure you didn’t just buy yourself a job.”

This piece of advice hit hard. One day, after a couple of years in, I was bartending at our wine bar and I was like, “oh fuck, I just bought myself a bartending job.” I swore I hung up my last bar rag in my late twenties. Very soon after that, I changed my perspective on hiring staff, rearranged the budget and started delegating tasks that I either didn’t like to do or just was plain not good at.

“I’ll Just Do It Myself.”

As a small business owner, it’s easy to fall into the trap of trying to do everything yourself. After all, your business is your baby, and you want to ensure that every aspect of it reflects your vision and dedication. I get it. However, trying to handle every task can quickly lead to burnout and limit your business’s growth potential. This is where strategic staffing comes into play.

Instead of buying yourself a job by taking on every responsibility, it’s essential to strategically hire staff or professionals for the parts of the job you don’t enjoy or aren’t proficient at. Not only does this free up your time to focus on what you do best (which is also where you make the money), but it also brings in expertise and fresh perspectives that can propel your business forward. Here are some steps to help you build your dream team and avoid the pitfalls of self-employment:

1. Identify Your Strengths and Weaknesses.

Take a step back and honestly assess your skills and preferences. What tasks do you excel at? What aspects of running a business do you find draining or challenging? By understanding your strengths and weaknesses, you can begin to identify areas where hiring additional help would be most beneficial.

Download the Skills + Preferences Worksheet

2. Define Roles and Responsibilities:

Once you’ve pinpointed the areas where you need support, it’s crucial to clearly define the roles and responsibilities of each team member. This ensures that everyone knows what is expected of them and reduces the likelihood of overlapping or neglected tasks.

3. Hire for Complementary Skills

When building your team, look for individuals whose skills complement your own. For example, if you’re a creative visionary but struggle with the day-to-day operations, consider hiring someone with strong organizational and logistical skills to handle that aspect of the business. By bringing in team members with diverse talents, you create a well-rounded team that can tackle any challenge.

4. Focus on Culture Fit

In addition to skills and experience, consider the cultural fit when hiring new team members. Look for individuals who share your values, work ethic, and passion for your business’s mission. A cohesive team that shares a common vision will be more motivated and productive in achieving your business goals.

5. Invest in Training and Development

Once you’ve assembled your team, invest in their ongoing training and development. Provide opportunities for skill-building, professional growth, and cross-functional training to ensure that your team members are equipped to handle evolving challenges and responsibilities.

6. Delegate and Empower

Trust your team to take ownership of their roles and make decisions autonomously. Delegate tasks and empower your employees to innovate and problem-solve independently. This not only relieves you of the burden of micromanagement but also fosters a sense of ownership and accountability among your team members.

7. Regularly Evaluate and Adjust

As your business evolves, periodically evaluate your staffing needs and make adjustments as necessary. Be open to feedback from your team and solicit their input on areas for improvement or areas where additional support may be needed. Flexibility and adaptability are key to building a successful and sustainable business.

In conclusion, building a successful small business requires more than just hard work and dedication – it requires strategic staffing and delegation. By identifying your strengths and weaknesses, defining roles and responsibilities, hiring complementary team members, and fostering a culture of empowerment and continuous learning, you can avoid the trap of buying yourself a job and instead build a thriving business that can flourish and grow for years to come.

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We’re Katy and Dale, or Dale and Katy depending on who you ask.  We are a married team that combines creativity, craftsmanship, and a shared passion for making dreams a reality. We’re currently embarking on an exciting journey to build our forever home on 8 beautiful acres just outside Madison, Wisconsin.

I’m Katy—a life coach and podcaster with a love for designing spaces that are warm, authentic, and filled with purpose. I’m all about turning ideas into reality, and this home project is the ultimate way for us to create something that truly reflects who we are, together.

Dale is an incredibly talented woodworker and a specialist in countertops and flooring, but honestly, there’s nothing he can’t do.  His eye for detail and “can-do-anything” attitude have been crucial as we dive into the many DIY projects that come with building a home from the ground up. He’s the hands-on expert, and together, we make a great team.

For us, this journey is more than just building a house—it’s about creating a space that’s true to our values and reflects how important our surroundings are to us. It’s about designing a home that embodies our love for family and nurtures our deep connection to the world around us. Whether we’re working with local artisans, sourcing sustainable materials, or getting our hands dirty with the next big project, we’re committed to making our dream home truly extraordinary.

We’re excited to share this multi-year adventure with you, and we hope our experiences, insights, and inspiration resonate with anyone who’s ever dreamed of building something special.

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