Feeling Financially Confident in Your Business with Madison Brown

October 31, 2022

Reading Time: 6 minutes

How to Feel Financially Confident: Make Time for Routines, Cultivate Your Dream Life, and Know Your Numbers with Madison Brown

Whether we like numbers or not, all business owners have to work with them on some level! On today’s episode of the podcast, I’m talking with Madison Brown, an accounting expert and time management superstar, as she walks us through her favorite ways to take the overwhelm out of dealing with your numbers.

How to set boundaries


Financial confidence doesn’t come naturally to everyone — or every business owner. Wife, mom of two, and master bookkeeper over at Madison Dearly Bookkeeping — Madison Brown truly does it ALL! 

She spends her time working with creative, online business owners who never got into business to do bookkeeping — but as Madison says, bookkeeping is non-negotiable when you have a business! She helps entrepreneurs find their expenses, profits, and bottom line numbers to inform their business decisions and find financial confidence.

Before starting her own business, Madison worked at a public accounting agency, which meant she was working somewhere between 60-80 hours a week on the regular. 

Now? She works 20 hours a week while making a great salary than she used to, thanks to her new outlook on the true meaning of productivity. 

Sustainability is a choice

Creating this sustainable 20 hour work week wasn’t an overnight success. Madison needed to make conscious decisions as she grew her business, especially as someone who came from such a fast-paced agency environment. 

This looked like allowing herself more time to do tasks, moving at her own pace, and only working with people she enjoyed. 

The basis of it all? Client relationships. 

Understanding her clients as humans first

Madison might work with numbers all day, but the reason she’s able to see to her clients’ success is because she understands them as a human first, and uses that to inform their financial decisions. 

Each quarter, she has a sit down with her clients where they dive into their finances AND goals. They talk about how to use their life goals to inform their financial decisions, bringing personality and joy to something that can often be intimidating. 

How does she get all this done? 

Having such a human-centric business requires Madison to put herself first, as well, which means having carefully structured time that allows her to take as much space as she needs. 

Both of her kids are in daycare Monday-Thursday. On those days, she works about 5 hours a day and takes a 2 hour lunch. And then, Friday through Sunday is wholly devoted to family time! 

Madison still balances a full client load and bookkeeping work in those 20 hours, without feeling stressed or overloaded. 

The keys to cultivating her dream life

Madison was absolutely glowing when she was talking to me about all this. Which made me wonder… how did she get to a point where her dream life was the norm? 

Reverse-engineer your goals

Madison first decided on her goals in life. What did her ideal everyday life look like? 

Once she had that, Madison used Google Calendar to time block her days with activities and work that would move her closer to her goals. For example, one goal was a 2 hour daily lunch. So now, Madison’s Google Calendar has a 2 hour block around 12 every weekday! 

I love that Madison talks about the “ideal” day instead of the “perfect.” Perfect sets us up for failure — because it doesn’t exist. But ideal is so much more like a goal! 

The design your life challenge

Madison credits Ashleigh Foy with helping her start the journey to her ideal life. She went through Ashleigh’s 5-day challenge to brain dump her ideal life and situation, and then use that to structure her calendar in a way that allows her to do what she wants to do. 

For example, Madison’s morning routine is listed out step-by-step in her calendar, and includes everything. From morning supplements to skincare to Bible study, blocking each activity out in her calendar for the morning time gives Madison a clear action plan to follow to meet her goals. 

When you get into these intentional habits day after day, they become second nature. There’s no such thing as putting too many things down in your calendar! 

Mitigating the overwhelm

I don’t know about you, but my first instinct when I think of putting everything down into my calendar was that it would be overwhelming. So I had to know how Madison deals with that so the overwhelm doesn’t hold her back! 

“It might seem overwhelming at first, but you need to look at how you execute it.” 

This routine works really well for Madison, but it might not work immediately for you. However, learning how Madison structures her day and manages her time can help inspire you to add another tool to your toolbox! 

Madison’s favorite tools

In her personal life, Madison lives and dies by her Google Calendar. She’ll even write down her most important goals and habits on a piece of paper and tape it to the fridge! 

For her business, Madison loves using ClickUp to organize her projects. She also uses Dubsado to manage her clients and keep track of her workflows, as well as Xero for accounting.

How can we take the intimidation out of our numbers? 

Have you ever felt like you might have filled out a form wrong while doing your taxes and then worried that the IRS was going to arrest you? 

I definitely have! I needed to know Madison’s best advice for taking the intimidation out of the numbers. 

She pointed out that money and emotions are always going to be intertwined. But how can we take the emotions out of it so that we can make better financial decisions? 

Look at your numbers objectively

Sometimes, it’s as simple as sitting down once a week and going through the numbers from a completely objective point of view. How much money came in the door? How much went out? What’s the bottom line? 

Then, take that information and shape it for the rest of the year. This isn’t going to feel natural right out of the gate, but the more often you do it, the more objective you’ll become. 

The same tactic can be applied to your personal finances. A great way to do this is by using a software like You Need A Budget or Mint. 

Have a plan

We can always feel intimidated by numbers when we don’t have a plan. But when we do know exactly how we want to move forward (and why we want to do it that way), we can take even more of the emotion out of it. Then, it simply becomes about next steps. 

Whenever you feel overwhelmed, intimidated, or emotional about something, it’s great to step back and just give yourself a plan. That in and of itself will make your brain feel so much less overwhelmed. 

Asking for help

Especially as women, it can be so difficult to ask for help. We feel like we should be able to do it on our own, or we might have asked for help previously and not gotten the right kind of help, which led to us doing it all on our own anyways. 

But what you really need to do is ask for help in a way that sets you up for success! 

The first thing you need to do is set up a system and process so that you can easily hand it off to someone. The second thing to remember is that when you’re asking for help from someone who genuinely loves what they’re doing (like Madison with bookkeeping), you’re giving them a gift! They get to do more of what they love, and you get to delegate a task out to the experts. 

The best piece of advice Madison has for anyone who’s struggling to let go is to focus on the rewarding results you’ll get once you DO ask for help! Whether you do it or outsource it, the result will be the same. But if you outsource it, you’ll take so much of the stress out of your life along the way, which means you can enjoy the results so much more! 

If you’re looking to ask for some help in your business bookkeeping, Madison would love to hear from you! You can explore her website here. 

In this episode, we talk about: 

  • How to build sustainability into your schedule
  • Madison’s backwards method for cultivating her dream life
  • 3 ways to take the intimidation out of your numbers
  • Why asking for help is the strongest thing you can do

Resources Mentioned in this Episode

Related Episodes

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