Julia Pimsleur
4 min readDec 16, 2022

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When Money is “Cringey” and What to do About It

Written By Julia Pimsleur

“When it comes to saying this is my fee and here is what it will cost, I feel sort of pushy or cringey. I wish I didn’t, but I do!”

Claire said this at a recent “Make More Money” workshop I was teaching. We were talking about how to state our price with confidence and get close more deals. She is far from alone, as many women have said the same thing, using terms like “icky” and “out of integrity.”

Why is talking about money such a big issue?

Like most things that hold us back, it’s largely because we were socialized that way. Most women were not raised discussing money around the dinner table, and then we don’t receive much (or any) basic financial education or sales training in school. This becomes a problem when you own a business and getting to six and seven figures depends entirely on your ability to close deals.

Money is not cringey to me because I was socialized a little differently. Having lost my dad at an early age, I was raised by a hard-working single mom, and money was definitely a big topic. She was a teacher at a local college, and raising two kids on that salary in New York meant I started working after school jobs at 13 and paid for most of college through waitressing. Years later, as a nonprofit fundraiser, my performance was directly tied to the amount of money I brought in. For five years I spent every day looking at how many donations of what dollar amount we needed to make our goals, and then asking people to make gifts of $1,000, $10,000 and $100,000 — sometimes ten per day.

This fluency in money came in handy during the 2008 economic crisis. I had my own business, and times were tough. People were only spending on items they considered mission critical. I realized there were just two ways to get through the recession: cut expenses (and we were already running pretty lean) or get better at selling.

I picked option two. I invested in myself, and took multiple sales training programs that taught me things like the psychology of a buyer, how to price for value, and how to get from “hello” to “yes” in one phone call or meeting. That saved our business, and eventually allowed us to get to $600,000 in revenues and bring on our first full time sales person, who helped us get over that magic $1 million dollar mark.

Right now it feels like deja vu of those lean times in 2008. A recent CNBC survey showed 51% of small business owners describe the economy as “poor” and 28% expect revenues to decrease over the next 12 months. In a time like this, we can cut expenses or learn how to sell more.

I hope you will do what Claire did and choose option two. We can get “re-socialized” about money and learn to actually like selling. Then we can teach our friends, teams and daughters the money skills that we should have learned in the first place. Because the only truly “cringey” thing about money is how unevenly it is still distributed.

BTW, Claire went on to close a $30,000 deal a week after the workshop! Easy peasy. When was the last time you boosted your money skills?

Stay brave,

Julia

P.S. Watch Kelly Burgess, Million Dollar Women grad and Founder of marketing agency Burg + Co, share how she brought in another $75k to her business by learning new sales skills. Click here.

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