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YOUR RELATIONSHIP WITH RISK

August 6, 2025

Rooted in your own experiences,

your risk relationship can change over time

 

 

Your own relationship with risk is shaped by the experiences you’ve had:

the beautiful, messy, complicated, and yet simple moments that when strung together, create your story.

By Meg McKeen, CIC


It’s one of my most favorite topics to chat through with a group of insurance professionals: risk taking.

There’s an assumption we often make that as people who’ve made a career out of managing risk, we have an above-average tolerance for it, but you all share with me regularly that it is, in fact, quite the opposite.

When you see the downside of risk-taking play out day after day in the form of accidents, injuries, and loss, you might think twice (or three times!) about upsetting your own status quo.

As we consider our own relationship with risk, I remind myself that my own relationship is rooted in my own experience, as is yours, and it’s a relationship that can change over time.

What gets in the way

Perhaps it’s a move—of your home or your job or your couch—or a relationship shift or change or even a new haircut that you’re pondering. If there’s something on your heart or mind that you’ve been considering, and to pursue it feels like a risk, it might be helpful to consider how your personal circumstances, the opinions of others, and your own beliefs about what’s possible for you might be influencing your thinking for better or worse.

I hear often from individuals that they feel like they’re meant for something else, something more. But their obligations keep them rooted firmly where they are, and then they apologize for referring to their obligations in a seemingly negative way. The reality is that many of us reading this are the primary income-earner in our family; we are also the glue that keeps the household running. To upset that balance might feel impossible or a risk not worth taking.

A dear friend and mentor told me years ago that I care too much about what other people think. It stung to hear but she was right (about that and many other things). I would often run my decision-making through a “how does this choice change how I am in relationship to others?” Will I be more or less valuable? More or less often considered? And, let’s be honest, more or less attractive through their eyes?

As a younger woman who followed a prescribed path of education then career then family to choose a different path in nearly every way has changed the way I relate to others, including the friends and family in my life. When you choose to show up differently, it can be uncomfortable and even confusing for others.

I acknowledge that for me, and maybe for you, too, this tendency to be who others see us to be has been a lifetime of learning and unlearning in this new season.

You might be carrying with you some stale beliefs about your own capabilities, too. When I tried out for the cheerleading squad in junior high and didn’t make it, I declared I wasn’t athletic. It’s a belief I carry with me today, despite having finished long-distance runs and holding my own in barre class these days.

In the earliest days in my consulting practice, I also branded myself a quitter, and assumed that, like the tennis team, a past relationship or two, and more than one hobby, I’d quit this business, too. My own evidence and yours, too, tells a different story, of course.

My experience isn’t yours and the anecdotes that come to mind for you won’t be the same as mine. But can you start to identify how your own sense of obligation, the opinions of others around you, and your own belief in yourself might be coloring your relationship with risk?

I encourage someone feeling this way to carve out time for herself—even just 30 minutes on a bench at the park or in her favorite coffee shop—to allow your mind to wander. Write down all the different ways you could show up differently in the world and then reflect.

Perhaps it’s not something so drastic (or dramatic) as selling your home and your things and traveling full-time like it was for me, but, rather another expression of yourself that can help you shift towards a better alignment between your purpose and your current viewpoint.

Where do we go from here?

Once you’ve granted yourself what might feel like permission to daydream, now it’s time to understand the facts. If your dream was like mine (for a very fleeting moment), do the research to determine how much it would actually cost in time and dollars to open a boutique vegan bakery in your quaint downtown.

If the risk on your heart is doing your own thing, how long is your financial runway before you have to go “back” to corporate? When I made the decision to stop dying my silver hair, you bet I did my own research—all the different ways I could transition, how long it would take, and how I’d navigate shame or embarrassment if I felt either along the way.

Making decisions from an informed place means you make fewer assumptions and excuses as you consider what’s right for you.

If you’re like me, and those voices of others speak loudly to you, be mindful of your inputs. Perhaps your closest friend of 30 years isn’t the best one to be giving you life advice in the season you’re in today. We can still love and appreciate what these relationships provide for us and also acknowledge that we need something different.

Also consider the media you consume; if all you see while you scroll are people who think and act like the “before” you then it might be time to change whose wisdom you’re taking in or set your phone to the side.

The author Sue Monk Kidd has said that “the body knows things a long time before the mind catches up to them.” Our bodies are amazing tools that are accessible always to us, and if your own gut instinct is like mine, you’ve heard what it’s told you at different times, but you haven’t always listened!

Whether it’s your gut or a tightness in your chest or a flip in your belly that signals that something is amiss for you, know that you aren’t required to take any action at all just by tuning in to what your body might be trying to tell you. Will you trust yourself enough to listen to it?

Your relationship with risk is yours

In a conversation recorded for the podcast I host, Guinness World Record holder Renee Bruns shared not about the risk she took—to travel the world in a wheelchair—but rather the feeling she didn’t want to have if she didn’t take the risk, and that’s regret for what she might miss out on.

Of course, not all risks we take will work out; not all of them will pay off. But the upside of risk, the possibility that you take that risk and it goes better than you could’ve hoped or even imagined for yourself, is real, too.

Your own relationship with risk is shaped by the experiences you’ve had: the beautiful, messy, complicated, and yet simple moments that when strung together, create your story. But your story isn’t yet finished.

So if there’s a risk sitting on your heart today, will you lean into that curiosity and practice trusting yourself just enough to take that first step to follow it?

The author

Once told “you’re someone I’d like to receive bad news from,” Meg McKeen, CIC, founded Adjunct Advisors LLC in 2018 with the simple belief that we can and must do more to support the individuals who choose a career in the insurance industry. Now in her 25th year, Meg’s experience working in underwriting, leadership, and sales within the industry informs her work as a consultant today, in which Meg now holds space, at the crossroads of personal and professional development, for insurance professionals as they navigate their shifting relationship with work and this current hard market. Meg’s work includes private and small group coaching, workshop facilitation, industry event speaking and planning engagements, and the podcast she hosts, Bound & Determinedsm. Learn more at www.adjunctadvisors.com.

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