Last week, I was interviewed for an upcoming event and was asked about my entrepreneurial journey – the good; the mistakes; and the lessons learned. It was a great conversation, and I appreciated the reflection it prompted. 

Perhaps it was because of the interview. Or, maybe it’s because I’m getting ready to host the Pricing Made HumanⓇ Masterclass next month. But, I became nostalgic afterward. Especially with regard to the key dates, moments, and decisions that have shaped the business I run today. 

Interestingly, not much about my business has changed since 1995. Sure, I no longer manage money. But the speaking arm of my business has been around since 1996. I signed my first coaching client in 2001. I started my email newsletter in 2003. My book was published in 2009. 

Speaking, coaching, writing – then. Speaking, coaching, writing – now.

However, my relationship with my business and my roles in it, as well as what I charge, have evolved. And rather immensely!

Everything Evolves 

One of the things I emphasized during the interview was how everything evolves

Here are two examples:

Example #1 – When I started my business and managed money, my company was registered with the U.S. Securities and Exchange Commission. I charged my clients an assets under management fee (AUM), a percentage that was shaped by industry standards. Plus, I operated in a regulated industry.

Whereas I didn’t have to give much thought to my pricing when it came to my role as a money manager, I did with my coaching services. 

And that was unchartered territory for me. Plus, coaching is an industry that isn’t regulated and there aren’t any industry standards, per se, when it comes to pricing. 

For me, the absence of constraints represented an odd combination of freedom (to charge whatever you want) and fear (how will people react to your prices?).

By the time I started coaching, I had nearly a decade under my belt managing money and five years growing the speaking arm of my business. While there is always room to improve one’s craft, I was confident in my money manager/speaker for hire roles. 

But, I had yet to find my “legs” with my coaching services. 

So, due to a medley of underconfidence and comparing myself to others, I spent far too many years undercharging for my expertise, experience, perspective, and the results my work helped people achieve. (Much to the chagrin of my mentors!)

For instance, in 2001 I charged $250 per coaching session. Today, I charge $10,000 for a six-month coaching engagement with entrepreneurs and small business owners. With singles and couples, as regards their personal finances, it’s $3500 and $4500, respectively. 

My speaking fees have also increased over the years. And, I am now licensing the recordings thanks to an example from “Client P” (yes, I learn from my clients, too!). 

Now, after 20 years, one might say the jump in the prices I charge for coaching and speaking isn’t huge. But, I don’t look at this only through the lens of the numbers; it’s not just a mathematical equation. 

To me, this is about me learning to  “catch up” to what my business, my life, and my money needed from me! 

Is your business, life, and money waiting on you to “catch up?”

Example #2 – In 2011, two years after the pub date of my book, I had the “bright” idea to create the TED of money. Inspired by their format, my idea was to curate speakers to talk about the intersection of love and money from different perspectives, and to take the show on the road. 

The plan was to do a five city tour; we made it to two: NYC and LA. In the middle of planning the Chicago event, I pulled the plug. As the event’s producer and organizer, I was underwriting the financing and bleeding way too much money. Not to mention feeling demoralized and depleted of energy.

During the interview, I shared how this experience helped me see that what at first blush seemed like a sales problem (not selling enough tickets/sponsorship packages), was, in fact, an audience and business model problem. 

This is one of those lessons that keeps on giving, because ever since I use every opportunity I can to remind folks to look beyond the problem they can see. Because more often what you can easily see isn’t what needs fixing. What you can see reflects a by-product of what does!

The conference experience was another pivotal moment in my entrepreneurial journey. It is when I made the decision that I would no longer give my business everything – including my financial future.

When you go beyond the problem you see, where are you being invited to make some adjustments regarding how you approach and make financial decisions?

Context Matters; Then, Today, Tomorrow

Twenty-seven years later, what I offer may seem the same, but a lot is different! 

I’ve changed. The way I coach and present have changed. My coaching framework is much more developed. My speaking engagements are less “technical” and more experiential. Who I’m seeking to “call-in” as clients has changed, as well. 

And my confidence in my entire body of work and with running a business is much, much greater!!  

When I started my business, I was 29 and naíve about the difference between being good at what one does and being good at running a business

I was also naíve about my power to determine what role I wanted money to play in my business and life. (That irony is not lost on me!) But, it was true back then because I was deeply committed to being the “model” entrepreneur, which tends to call for putting your business first and your personal finances last. Clearly (and thankfully), I no longer subscribe to this mindset! You can even ask my clients; in our work together, we center the health of their personal finances when making business decisions.

But, I don’t have to go all the way back to the beginning to spot the difference between then and now. I’ve made some subtle, yet impactful changes to my business since the start of the pandemic. Plus, what I now need from money and what it now needs from me, has changed – again.

How about with you: What’s changed in your professional life – whether you go back several decades or several years? And how has this affected what you need from money and what money needs from you – today? 


Søren Kierkegaard says, “Life can only be understood backwards; but it must be lived forwards.” I think about this quote as it relates to evolution. Because you typically only notice what has evolved upon reflection, after it has occurred.

Though, there is a way to “speed” up the process of awareness. You do so by asking questions – questions about your current behavior and choices. Along with questioning if the assumptions you’ve made about the future still hold true. 

As I mentioned, I’m hosting the next Pricing Made HumanⓇ Masterclass  on Thursday, June 9th at 4pm ET. And, I’d love for you to join us. Especially if you’re not sure if your prices really reflect your current evolution in terms of what you and your life need from your business and money. 

Be assured: We’ll ask the questions to help you discover if your business, life, and money are waiting on you to “catch up.”

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