Growing up, my mother would frequently say, 

“You win some; you lose some; and some get rained out.” 

Her words were no doubt an homage to baseball, and our shared love of the Yankees. And, it was often in response to me asking her some variation of, “How do I know if I should do “A, B, or C?,” when I was on the verge of making a decision and unsure of which path to take.

It was a response I always found unsatisfactory – whether I heard it at the age of 8, 18, or as a much older adult. 

Of course, I now see the wisdom of her response. 

Embedded in it, she was acknowledging my thirst for certainty and wanting to make the “right” choice. And without saying it directly, she was “teaching” me the importance of being comfortable with uncertainty. Because not all decisions have clear-cut, objectively “right” or “wrong” answers

Plus, she was helping me get comfortable with the fact that regardless of the choices I make, I won’t always get the outcomes I’d hoped for.

I lost my mother nine years ago. Now, I’m the one saying to myself and others, “You win some; you lose some; and some get rained out.” 

I’ve really come to appreciate the counsel in her go-to response, because in a way she was teaching me to pay attention to my intuition and how I go about making decisions, and to trust myself.

Math; The Easy Part

Last week I had the awesome pleasure and privilege of sharing the virtual stage with Erin Halper, founder and CEO of The Upside, for the Sales Roundtable hosted by sales consultant and teacher, Allison Davis. The focus was on one of my all-time favorite topics: pricing.

We had a blast! 

Our conversation, the questions from the attendees, plus a moment I had of my own (that I’ll tell you about in a jiffy), reminded me of this: 

When you get right down to it, the simple part of managing* money (or setting your prices) is actually the math of it. 

You’re either adding or subtracting, or multiplying or dividing. And, whatever computation you’re unable to do in your head, there’s a calculator nearby to help you out. (Mine is a HP 12c financial calculator.) 

The simple part of money is ensconced in the common financial tenets you’ve definitely heard before; heck, you may even diligently put them into practice: 

  • Pay yourself first
  • Spend less than you earn
  • Have minimum to no debt
  • Invest

These tenets are mostly espoused when it comes to your personal finances. Truth is that they apply to your business finances, too. 

It’s my opinion that the math part of money can give us a false-sense of certainty. 

However, the pitfalls begin to emerge when, as some might say, “the math isn’t mathing.” 

This colloquial expression perfectly conveys the frustration and confusion one feels when the expectations of the “math” fall short. 

I’ve said this before, and I’ll continue to say it because it needs to be continuously reinforced. Especially when there is so much noise that says financial success is a by-product of just crunching numbers and/or engaging in complex financial strategies.

Mastering the numbers is one thing. 

Mastering the multi-faceted domain of the emotions of money (and pricing) — now, that’s quite another.

Then, There’s This

Perhaps my perspective is a bit biased given my body of work. But to me, the emotions of money (and pricing) were on full display last Wednesday. Particularly if you go beyond the words of the questions that were asked. 

Here’s an example: There was a question about when to introduce pricing into your discovery/prospecting conversations, especially if you’re concerned your price point may be higher than their budget.

Here’s what that question is really about: Identity, status, positioning, and acceptance. 

What do your prices say about you, your business, and the promised value of your offer?

Yes, status is subjective. But, do your prices convey the value, quality, or exclusivity you want your prospect to perceive?

What do your prices convey about where your offer fits in the marketplace relative to your competitors or alternative options (including doing nothing)? 

Even though we know “no” is part of the sales process and shouldn’t be viewed as a personal rejection, getting them can often feel like a personal affront. Like, “Oh no, I said my price and they said, ‘That’s too high.’ They’re rejecting me.” 

Another aspect of this is, which is not talked about enough: not wanting to be perceived as being “inaccessible” and inflexible. So, maybe you don’t want to be the one to say, “no, this isn’t right for me.” 

And, here’s a confession: During the roundtable, I had a moment myself when I felt unsure about my own approach to pricing. It came after I shared the starting price of my speaking engagements ($12,500). I wondered, “Oh no, will they think that it is too little?” (Isn’t it interesting how I wasn’t concerned about whether someone thought it was too high…?!)

Yes, the realm of emotions, money, and pricing is the work I do with others. It is also the work I continuously do with myself. 

More Than Meets the Eye

The question the attendee raised was about more than the words of the question. 

All of them were, actually. 

This is true with many questions, and especially so whenever money (or pricing) is concerned.  

Plus, the question spoke to where the person felt unsure about her choices and the possible reaction/outcome as a result of. This moment of doubt isn’t unique to her; this is part of the universal experience of what we call life and business.

But when you break it down, her question was also about these unspoken questions

Like, how can I: 

  • Reduce my uncertainty about what choice is “right” or “wrong;” 
  • Boost my confidence and validation about whichever choice I make; and
  • Avoid any regret with whichever choice I make if I don’t like the results?

You and I have to contend with this conundrum, too. It surfaces when the questions are about money, in general, or pricing, more specifically. Or, life and business, overall.

And, while you and I can follow a framework to help us get to the answers that are right for us, sometimes our expected or predicted results still don’t materialize.

So, the next time you feel unsure of which choice to make or of which path to take, tap into the wisdom of my mother’s words:

“You win some; you lose some; and some get rained out.” 

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