If “Failures are finger posts on the road to achievement,” as C.S. Lewis suggested, my opportunities for achievement are many. Indeed, the only reason that I have an opportunity to share this insight with you today is that I failed at one person’s version of financial advising.

Although very real, that person was a mythic amalgamation of Michael Scott, Steve Carell’s legendary manager character on The Office, and Alec Baldwin’s motivational speaker “from the home office” in Glengarry Glen Ross. He’d almost surely dispute the former parallel but take pride in the latter.

He was the regional leader of a major life insurance company, and I was one of the new twenty-something recruit class that was his to mold. I had already been shot down to become a member of the “bullpen” at the biggest brokerage firm in town because, despite a few years of experience in the field and all the requisite industry licenses, I had neither any sales experience nor a natural-born network of monied connections. Sales was what I’d learn now—or, at least, it is what I would be taught.

In this class, I was first taught to buy a car I couldn’t afford to simultaneously project an unmerited air of affluence while creating an outsized financial hurdle to chase, a bloated monthly car payment, to motivate me to sell.

I was taught to keep my hair short, my face shaved, my shoes shined, and my neck bedecked with a conservative power tie to complement my (only) navy blue pinstriped suit. Plain white oxford shirts were expected to be starched and worn every day of the week but for Wednesdays, when light blue or light pink shirts were allowed.

I was taught to carry this façade into every place and interaction—yes, including the grocery store and the gym, where we were also instructed to enter and leave in a suit. I was taught what my favorite restaurant would be to invite a prospect if I managed to attract anyone of means to a meal. I was instructed to arrive at the restaurant early enough to create a faux familiarity with the maître d and the server, even including a contrived drink, “the usual,” which was anything but.

Regardless of my actual identity, I was taught to play a role.

And that wasn’t where the roleplay stopped. We were taught to act as holistic financial advisors, even to use comprehensive financial planning, to sell a product—in this case, cash-value life insurance underwritten by the company we worked for.

Of all that I was taught, what did I learn?

I learned that there is value in keeping your shoes clean—and that I simply couldn’t play a role that far from my identity.

However humorous this story appears to be in retrospect, it ushered in an important but challenging time in my career. While I can see the dilemma (and the solution) clearly now, the process of reconciling my identity and my role as a financial advisor took years—and two decades later, I’m sure there is still more work to be done.

In fact, just this year I learned about the I/R—or Identity/Role—Theory, perhaps ironically, from Mark McGraw, a Sandler consultant specializing in sales and leadership. Here’s a quick synopsis:

• Our Identity (I) is who we really are. Although formed over a lifetime, this includes our core values, beliefs, and self-image.
• Our Role (R) is how we behave in a specific situation, which can change depending on the environment or circumstances.
• The Theory is that when our I and our R are in alignment, we feel comfortable and act authentically—and when our I and our R are in conflict, we feel stress and may act inauthentically.

My personal belief is that we can’t do our best work or be our best selves when we don’t have I/R alignment. Or perhaps better said, we can be and do our best—personally, professionally, and financially—when we have Identity / Role alignment. And because our Identity is so deeply ingrained, it is likely that our Role needs adjustment when we are out of sync.

I’ve given you a detailed example of I/R alignment related to my profession, and I wonder what this looks like for you. How well aligned is your professional Role with your personal Identity?

While we’re tempted to presume that the key indicator here is whether you are “successful,” I believe the key indicator is whether you feel whole and fulfilled in your work. I’ve known too many successful people who hated their work to believe otherwise.

And how about financially? Much like my cartoonish sales manager, many of the financial prescriptions offered—especially from financial “gurus”—are highly aligned with their identities. But how about yours?

Is your financial plan a manifestation of who you are? Or is it made in the image of your financial advisor or financial guru du jour?

A key indicator may be whether you’ve been successful in following the recommendations. However, an even better sign is whether your financial planning genuinely represents your personal values and goals. Is it your fingerprints showing up all over your plan—or someone else’s?