• When it comes to money, what’s the biggest challenge you have or area you want to improve?
  • What does success look like in relation to this? 

These are just two of the questions I ask people before we even get on a discovery call. Their answers to these and other questions are what we dive into during our call.  

For a recent prospect, she was wrestling with whether she should leave her job to start her own business. She wondered if she was letting the financial stability of it influence her decision too much. She also shared how she didn’t want to worry about money. 

Let’s just say she was surprised by answers. She was even further surprised when I said her questions represent a healthy curiosity – not a dysfunctional relationship with money.

Why am I sharing this with you? 

Because perhaps you can relate: When she told someone she trusted her concerns about why she was hesitant to leave her job, they suggested she might need to work on her relationship with money.

Has anyone ever suggested you need to work on your relationship with money. Have you wondered if you should yourself? 

Look, we all have a relationship with money. And like any of our significant relationships, there are times when it is healthier than at other times. However, to turn a valid question (should you leave or stay?) into a scenario that causes you to wonder if there’s something wrong with you…well, that’s a whole other ball-game! 

Here’s the thing, if the comment that led her to me had come from a friend or family member of hers, it wouldn’t have bothered me as much. BUT, it came from a professional. Now, that pissed me off! 

Wanting to be financially prudent doesn’t mean you have an unhealthy relationship with money.

If anything, it means you’re being smart and strategic. 

In case you’re wondering, I suggested she stay at her job and start her business as a side-hustle. 

At least until she has several clients under her belt, and has created a new business development process. At least until she knows if her business model “works,” and has created a plan that gave her a better idea of how long it would take to get on a path to replacing her current income. Especially since her decision wouldn’t just affect her. 

I am a huge advocate for entrepreneurship. I’ve been waving my entrepreneurship flag since 1995. In fact, I want as many people as possible to hop on this bandwagon. 

But can folks please stop with the “all or nothing” binary thinking – with the idea that the only choice is to stay in your job, or leave and start your own business. Can folks stop making it seem as though those who choose to stay or do a hybrid have a “problem” with money.

If my suggestion to stay at her job surprised her. You should have heard her reaction when I said, “Not wanting to worry about money is the wrong goal.”

Some of my peers who work in the financial coaching space will tout how and why you shouldn’t worry about money. I call b.s.  

In my opinion, to embrace this means you’re not accounting for the dynamism of money. You’re not accounting for the fact that as you make “big” financial or financial adjacent decisions and/or reach new financial levels, what comes with are new roles and responsibilities – some financial, some emotional, some maybe even spiritual.

From my perspective, I believe a better goal is this: Not to find yourself worrying about the same thing year after year. 

New opportunities bring about new challenges, which bring about new (different) things to worry about. This doesn’t make you or your relationship with money deficient. 

That said, like much when it comes to money and life, it’s nuanced. 

Could worrying about money be a signal you need to work on your relationship with money. Perhaps. 

Or, it could also be an invitation to get curious about what you’re really worrying about. This is when applying the 5-whys becomes a beneficial practice. Asking yourself “why?” from a place of curiosity (not judgment) five times can help you get to the root – or real source- of what’s causing you to worry.

I am so incredibly grateful this prospect reached out. I’m sad that she was made to feel as if she didn’t have a “normal” relationship with money simply because of the very valid considerations she was weighing. But, I’m glad I was able to validate for her why it makes sense to stay and to give her some ideas on how to know when the time is right to leave. 

TL/DR: Questions are good. Simply having a money (or adjacent) question doesn’t mean you have an unhealthy relationship with money.

I suspect if she needed to be reminded of this, perhaps there are others in the same boat. So, pass it on.

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