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Ask Ashley: Overdrawn and Overwhelmed

Ask Ashley: Money stresses me out. How do I start to get a handle on my finances?

Ashley Janssen
Ashley Janssen
6 min read
Ask Ashley: Overdrawn and Overwhelmed
Photo by Josefa nDiaz on Unsplash

Welcome to the first edition of the Ask Ashley advice column! On the second Wednesday of every month, I answer a question from my subscribers, consulting clients, or social media followers on their biggest productivity challenges.

Have a question you want to submit for another edition of Ask Ashley? Shoot me an email. Questions will be anonymized and may be edited for clarity.


Dear Ashley,

Money stresses me out, and my coping mechanism is to avoid thinking about it. But not knowing what is going on is costing me money, and it isn’t buying me much peace of mind.

How do I start to get a handle on my finances?

— Overdrawn and Overwhelmed

Dear Overdrawn and Overwhelmed,

The first thing I want to tell you is you are not alone. Having blockers on how to manage the money side of a business is something I see with almost every one of my consulting clients. One of the things I always ask them is:

Why would you know how to build a cash flow spreadsheet or read a profit and loss report if you have never been taught?

It’s not like when you start a business you suddenly know these things.

But you do move past your mental blocks and learn.

Why understanding your finances is so important

As you said, it is expensive in both money and mental energy to avoid thinking about your finances. Not knowing your exact financial situation puts your business in a precarious position. You don’t have the information you need to make informed decisions about things like:

  • How much should you pay yourself?
  • Which projects should you accept?
  • What work should you prioritize?
  • Can you afford to hire?
  • Can you afford new hardware or to take a course or new software licenses or...anything really?
  • How much should you be putting towards debt repayment?
  • How much should you be putting towards taxes?
  • etc.

It’s not enough to know your bank account balance. It is vital to your business to know:

  • What is coming in and going out, and when?
  • How much money do you project to have in the future?
  • What are common trends over time and seasons?
  • What are different scenario projections depending on which projects come in or how many units you sell?

You have already acknowledged that you have some mental blocks around money and that something needs to change. Awesome!

These are a few things you can do to start getting a handle on your finances:

  1. Identify your money blockers
  2. Reflect on and record what you DO know about your finances
  3. Educate yourself
  4. Identify who might be able to help you and ASK
  5. Hire professional help

1. Identify your money blockers

You said, “money stresses me out”. It is helpful to dig a little deeper into where that thought comes from. Understanding some of the automatic thought processes (and spirals) that happen when you think about money is the first step to moving past them.  

Some questions to ask yourself to shed some light on your money blockers include:

  • What about money stresses me out?
  • What was my perception and experience of my family’s financial situation growing up?
  • What financial situations have I experienced as an adult?
  • What is my perception of those who are wealthier than me?

While the answers to these questions may veer into sometimes heavy topics (that are best left to a trained therapist), they can help to give you some context for where your feelings are coming from. We all started businesses to make money. Take a step back to get clarity on what's blocking you so you can think about what mental shifts need to take place to move forward.

Knowing there is a blocker is half the battle.

2. Reflect on and record what you DO know about your finances

You know way more than you think. You haven’t made it into adulthood and started your own business without learning a thing or two about how to pay bills, budget, pay taxes, and understand your bank statements. Dealing with these things still might be uncomfortable, but that doesn’t mean you don’t know anything.

Take some time to reflect on what you DO know or information you could easily find:

  • What are your revenue sources?
  • What are your salary costs?
  • Do you have payroll deductions?
  • How much do you pay subcontractors?
  • What are your recurring monthly chequing expenses? Things like an office lease, insurance, parking, tax instalments.
  • What are your recurring monthly credit card expenses? Things like software licenses, Google ads, hosting.
  • What are your recurring annual expenses? Things like a business license, accountant fees, lawyer fees.

Make some lists. Most of these come right from your bank statements. Once you have them, you are most of the way to having a cash flow spreadsheet!

3. Educate yourself

When you don't know something, the best thing you can do is arm yourself with information. Like any new project, doing a little research will go a long way to set you up.

You don’t need to go crazy and spend a ton of time or money, either.

A good place to start is your local startup supporting organization. If you are in a large enough city, they likely put on financial literacy courses regularly. Alternatively, try a Google search for something like, “small business financial literacy webinar” or “small business financial basics” and include your country or region and see what comes up.  

Here are some examples that I got after a quick search that would be a great start:

Business Development Bank of Canada (BDC)
Money Smart for Small Business (MSSB)

Spend a few hours educating yourself on the basics. Do a little reading (try We Should All Be Millionaires by Rachel Rodgers). Get comfortable with the language. It’s a safe, non-judgmental place to start.

Photo by Chris Montgomery on Unsplash

4. Identify who can help and ASK

Do you have anyone in your family, friend, or entrepreneur circles that could help you? Aside from the former accountants, most entrepreneurs have muddled through figuring out their finances in one way or another. Someone you know will likely have a template or two that they would be happy to share with you. But you have to ask!

I have a service business and this is the template that my cash flow spreadsheet is based on. Try to fill it out using the information you collected from your bank statements.

What’s the worst that could happen? See how far you get. You won’t know until you try! If you need more help (which is a reasonable expectation), then you can seek professional help in the form of a bookkeeper or consultant.

5. Hire professional help

When you have gotten as far as you can on educating yourself, seeking help within your circles, and seeing how far you get on your own, hire a professional to teach you the rest.

Hire a bookkeeper

Different bookkeepers provide different levels of service and education. Ask around in your circles or among friends and family. See if you can find someone that will teach you how to build reports from your accounting software. Those reports will provide you with the information you need to finish your cash flow spreadsheet.

Many bookkeepers will help you build a cash flow spreadsheet too if you didn't get that far.

Bookkeepers will also keep your accounting software up to date, make sure your payroll and tax deductions are done correctly, and ensure you have the information you need to provide an accountant at the end of the year.

Hire a coach or consultant

Different types of coaches and consultants also provide different kinds of help. There are financial coaches out there who are a great option to guide you through this process, as well as consultants like me who can help you with the basics before you move on to more specialized financial services.

If setting up your first cash flow spreadsheet is an option you want to explore, reach out and I will help you.

Even a few hours is a worthy investment to get started on understanding your finances.


Thanks for the question, Overdrawn and Overwhelmed! Feeling discomfort with how to manage your finances is normal, even common, but it’s something you have to work through for the sake of your business. You don’t need to become a financial expert, but you do need to know where your cash flow is to make informed decisions.

The key is to ask for help. You are smart, capable, and don’t have to figure this out alone. :)


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Ashley Janssen

Ashley Janssen

Writer, business coach, speaker, entrepreneur, chaos calmer, introvert, cat-lady. Lover of books, fitness, old fashioned’s, basketball, and video games.

Follow me on Twitter, and LinkedIn.


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