Five Ways to Build Psychological Safety with Money as an Entrepreneur

One of the reasons I was excited to bring my husband on as my co-founder in Pearl Spark Pages is because I wanted an excuse to avoid the financials. I’m happy to do product development, sales and marketing all day long but P&Ls? Cash flow statements? COGS? No thank you.

But that started to change for me when I met Megan Hale, the founder of DreamMoney™, a strategic planning software for female founders. Since she’s so good at navigating money and the nervous system, I've invited her to be our next guest blogger.

Here's Megan's perspective on how you can feel safe with money as an entrepreneur!

Photo Credit: Megan Hale

As a former psychotherapist who’s now a fintech founder, I’m obsessed with helping others create psychological safety when it comes to money. The biggest mistake I see most entrepreneurs make is assuming they just need more money to feel that sense of safety when the steadiness they crave comes from just “more money” alone.

How do I know? Before starting DreamMoney, I spent a decade as a fractional CGO (chief growth officer) helping my clients 4X-10X their growth sustainably. As they went from $100K to $1M or $200K/year to $200K with just one offer, the five money practices that were always the most profound were these:

1. Make saving a habit.

I’ve worked with thousands of businesses at this point being behind the scenes of their cash flow. In all this time and in all these businesses, I’ve never seen a business make the same amount of money every single month. Knowing how to navigate the natural rise and fall of cash flow is one of the most important skills to master if you want to feel solid with money. One of the biggest money practices to help with that is to make saving money a habit. 

It’s easy to splurge when you have a high-cash month, but businesses typically need at least 90 days to make a new cash month their new norm. It’s smart to get in the habit of saving a percentage of revenue so when you hit a lower than expected cash month, you have that cushion waiting on you.  

Most people underestimate the amount of psychological safety a literal “safety net” can create for you. This is why it should be prioritized early and consistently (even if it’s small at first). The peace of mind is everything! 

2. Know your numbers

Most entrepreneurs who come to DreamMoney may have an idea of a few of their numbers, but typically don’t have a way to see all their numbers as a whole. DreamMoney ensures every single user knows their Minimum Viable Revenue - the amount their business needs to hit that stabilizes their cash flow. Most entrepreneurs tend to avoid their numbers, especially when cash flow is low.  

This can lead to an increase in both fear and anxiety. You’re scared to look at how good or bad things really are and then you’re emotionally responding to a guess vs. facts.  

If you want to build psychological safety, you have to get comfortable looking at your numbers so you can make informed decisions. This is true when you’re having a great month and especially when you’re not.  

For the longest time, I felt like my numbers were going to tell me a truth I didn't want to know. When I could reframe my numbers as supporting my highest good and dreams as a CEO, I started to see my numbers as helpful vs. scary.

This is one of the biggest shifts we aim for as a company - helping our users build deep intimacy with their numbers so they can map their best next step from a place of clarity & power. 

3. Have a simple revenue strategy.

One of the most common mistakes I see solopreneurs make is having a complicated revenue strategy that has too many chances to fail. The most common denominator is not creating a strategy that’s sustainable for them to execute.  They try to do too many things at once instead of mastering a few strong revenue streams that create financial stability.  

One of the biggest things when it comes to psychological safety is knowing you know how to earn and you have a simple, repeatable strategy for doing it. We not only provide revenue planning tools so you can see your strategy all in one place, but also teach the foundations of sustainable business design to help all our users create meaningful business momentum. 

The one thing I wish everyone knew is that it's normal for big money goals to feel intimidating and even out of reach when you don’t have a solid plan for reaching them. 

That’s why it’s so important to know all your numbers from the amount of revenue you really need to be pursuing to sustainable price points to realistic sales goals.

When you have all these numbers working together, the “how” is right there for the taking. It’s then simply executing your strategy and getting better and better at lead generation and sales.  

4. Stay in the room.

When I first started creating psychological safety with money, the idea of even sitting with my numbers for five minutes was overwhelming. It’s no surprise I didn’t feel empowered around money when I felt like I wanted to jump out of my skin simply sitting with my financial reality. But I chose to do something radical and meet with my money every single day for a year.  

Some days, it’d only be for five minutes and I’d sit in the discomfort and barely breathe my way through it. Other days, I’d find myself sitting with my money for an hour going over all my numbers, dreaming up new dreams, playing with my business strategy, checking in on my bank accounts, etc. 

In a year’s time, my relationship with money had completely transformed. Looking back, I was giving myself my own version of exposure therapy allowing my nervous system to get used to being uncomfortable and staying in the room for just a few more minutes before moving onto something else. 

What that year taught me is nothing changes if you can’t stay in the room, but the minute you do, you open the possibility for a whole new reality! After all, we can do anything for just five minutes and that’s exactly where I recommend everyone start. 

5. Focus on earning more money vs just money mindset alone.

When I first made the shift from therapy to coaching back in 2015, I heard the term “money mindset” for the very first time and I felt like it slapped me in the face. It was a whole new genre of inner work and sadly I believed the standard narrative back then that if I wasn’t making the money I wanted, I needed to heal my money story first. 

What I wish I could go back and tell that version of me is, “yes, money mindset is important. But what’s even more important is learning how to sustainably earn.”  

Your mindset may impact your pricing. Your mindset may impact what you believe is possible.  But you can out-earn undercharging. You can out-earn self-doubt. I can promise you that you do NOT have to do the healing work first. 

It absolutely grinds my gears that women are disproportionately sold money mindset work when earning is healing in and of itself. That’s why I believe in taking an earning approach to shifting your money mindset.  You can earn and do the inner work simultaneously. And in fact, it’ll be the fastest way to shift your money mindset as you develop new money skills & perspective for managing your more cushy bank account. 

DreamMoney is a strategic business planning software that helps you: 

• Clarify meaningful revenue goals

• Map out sustainable revenue plans

• Dial in profitable price points

• Cast financial projections

• And expertly manage your cash flow. 

It exists to help more women make more money, but not just any type of money, but money that’s Deliberate, Reliable, Easeful, Abundant, & Meaningful.

Because when we’re tapped into DREAM, this is what creates psychological safety on every single level that goes far deeper than just money mindset alone! 

Megan Hale is the CEO & Founder of DreamMoney, a strategic business planning software designed for solo-CEOs who want to build their dream business by being more strategic about their growth. 

It’s the first platform that combines financial psychology with high-powered financial planning tools for small businesses. 

I’m a proud affiliate because DM has not only changed my business & financial confidence, but I’m 100% in on women-entrepreneurs building more wealth!  Start creating your custom strategic revenue plan at dreammoney.co.

Thank you so much for your guest post Megan, we're so excited to have you offer your Think Like a Chief Growth Officer training to our community on September 23, 2025 at 1:00 p.m. ET!