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“What is your height and weight?”

“Tell me what medications you take.”

“What exactly do you call your eye condition?”

These are just a few of the questions posed to me recently by a colleague who was helping me apply for an insurance policy. It was his job to gather all my health history so the insurance company could decide if I was someone they wanted to insure.

After the small talk and laughter, our call took a sharp turn toward the personal. This didn’t exactly come as a surprise. I knew he would need to know these things. I also knew that each time he asked, “have you ever had a history of…?” the best answer was a definitive no. After answering yes more than once, I noticed a few worrisome thoughts running through my mind. Maybe I’m not as healthy as I think I am. Am I going to be denied coverage? Does this guy think I’m a total freak?

As the questions continued, I started noticing and interpreting his every pause and exhale. When he said “mmhmm” I wondered what the heck that was supposed to mean. I thought by the end of the call he would tell me whether I was an underwriting train wreck, but instead he just thanked me, agreed to get back in touch and politely got off the phone.

When I hung up, I was caught off guard by how I felt. I hadn’t been nervous to have the call. I was familiar with how underwriting worked. After all, I’ve been the impetus for many people to apply for insurance over the years and had been alongside them through the process. Nevertheless, I felt exposed. Outside of the doctor’s office, I’d never had to share my health history with anyone, much less someone with whom I had a professional relationship. It’s just not what you generally talk about with people.

That’s when it occurred to me; I must be feeling the same way that most people do when they talk to a financial planner.

Being on my side of the table, it doesn’t feel at all strange or uncomfortable to talk about how much money someone makes, how much debt they have or who they want in their will. Of course, that’s easy because it’s not about me and my choices. When it is own our financial life up for discussion, the process can range from slightly uncomfortable to downright invasive.

We could chalk it up to money being a taboo topic in our society, but I don’t really think our hesitation is about whether it’s tasteful to talk about money with a financial planner. That explanation diminishes the emotional weight of the situation. Our hesitation is driven by two much bigger fears: the fear that we are royally messing up our financial life and that we are going to be judged for it.

By the time we meet with a financial planner, we have inevitably been forced to make loads of financial choices on our own. We decided what career to pursue, when and how much to save, what home and car we could afford or how to invest our 401(k). We made the best decisions we could, but we never had the financial context to know how these decisions might ultimately free us or limit us in the future. Of course, we hope the decisions we made will set ourselves up for success, but we also fear that maybe they won’t.

It’s easy to put those thoughts aside in the hustle of daily life, but the moment we sit down with an advisor, we know our decisions will be on full display. With nothing more than our entire life’s happiness at stake, we sit down to learn how we’ve done. Are we headed toward the good life or do we need to make wholesale changes to get back on track? If it’s the latter, we often feel disappointed, not just with the outcome, but with ourselves.

When sharing our story could result in both shame and a prescription for change, is it any wonder we avoid meeting with an advisor or try to paint a rosy picture when we do?

Now layer on top of that the fear that our advisor might judge us. Because money touches so many parts of our lives, financial planning involves sharing more than account balances and savings rates. A discussion on college might reveal that we disagree with our spouse about how much to pay. A review of our estate plan might uncover that we are estranged from a family member. An analysis of our insurance coverage might expose that we’ve battled addiction. A cash flow projection might shine a light on a spending issue.

We’re expected to open up about the most personal and private matters in our lives; the things we intentionally don’t talk about because we don’t want to be vulnerable to judgment from others. And we’re not telling just anyone; we’re confessing to a person we (hopefully) like and respect and who might seem like they have their life together more than we do. Our natural desire to maintain a positive regard in our planner’s eyes makes it all the more difficult to share.

The point here isn’t to send us running and screaming away from financial planning, but to highlight the courage it takes to find out how we’re doing financially and share the necessary information it takes to help our advisor be effective. FDR said “Courage is not the absence of fear, but rather the assessment that something else is more important than fear.” If we can focus on how much we want to put our kids through college, start a business, buy our dream home, retire on the beach or just make sure we never have to sustain on Ramen noodles, hopefully we’ll make it past the uncomfortable nerves at the beginning of the process. If that doesn’t work, keep in mind that if everyone who walked into a financial planner’s office was already doing everything right, they (and I) would all be out of a job.