Is your relationship with success healthy?

Michelle Krasny
6 min readSep 30, 2019

Michael Williams* and Rebecca Anderson* both had unstable, tumultuous and at times, even traumatizing childhoods. As adults, they continue to have more than their fair share of stressful life events (Holmes & Rahe, 1967) — relationships ending, moving, changing educations, changing jobs — but while Rebecca seems to be barely surviving her life, Michael is thriving.

What’s the difference between them, and what does it have to do with their relationships with success? At first I wasn’t sure… but let’s back up.

About a year ago, I got really fascinated by the idea of Impostor Syndrome (I wrote a previous article about it here). I read books and journal articles about it, and even gave talks and workshops on the subject. But over time, I became more and more convinced that Impostor Syndrome was just the tip of the iceberg, a symptom of something bigger and darker.

So I turned straight to the source — people. A few very generous folks, like Michael and Rebecca, volunteered to speak with me at length. I asked them a whole bunch of really nosy questions; about their families, their childhoods, the communities they’d grown up in, their achievements, their successes, their failures and the messages they’d like to be able to share with future generations.

And the more people I spoke with, the more a pattern emerged.

Many of the people I interviewed had some of the classic hallmarks of Impostor Syndrome. For example, Chirag Bakshi*, a 34 year-old Indian-American Assistant Professor was completely unable to internalize his own successes. “I actually don’t anything that I’ve done is any good, ever. So it doesn’t matter what I do,” he explained, despite objective successes like achieving a PhD at 28 or landing a great job offer. “I continually reevaluate where I want to be. And so I always feel like I have more to go.” This constant moving of the finish line is common to those who are stuck in the Impostor Cycle. By diminishing or invalidating our successes, on some level we believe that we are maintaining our ability to stay motivated, to stay hungry.

But what struck me as fascinating was how people answered the question “do you consider yourself a success?” In fact, it turned out to be the key to everything.

“Do I see myself as a success based on my own standard? No.” Rebecca told me.

An adult white woman standing on a beach

Rebecca Anderson is a 30-year-old white woman living with her second husband in North Dakota. At the time we spoke she was unemployed, having recently left her job as an Executive Data Processor because her office refused to deal with its bed bug problem. Objectively, Rebecca has had a lot of successes in her life. She bought her own car at 20, lost 40 pounds, went back to and graduated college as an adult. She left an abusive marriage completely on her own. “I had this bank account where I was stashing money to get away. I just stashed and stashed, and I was able to get out of there, myself.” But she still did not see herself as successful.

“For me,” she said “success is based on finances. You know, social security isn’t going to be around when I’m retiring, so what do I have to do to be able to plan for my life and everything that I’ve become accustomed to in my life.” She believes that successful people are “self-reliant and resilient.” She held her mom up as an example. A woman who, despite being dealt a “pretty crappy hand” always got back up. “You can’t knock this woman down. People have tried, and to me that screams successful. She’s very motivated, she doesn’t let anyone tell her what to do, she’s going to do what she wants to do.”

When I asked her what it would take for her to consider herself a successful person she replied “it would just be not having to depend on my husband like I have…. Like my car payment, although it is my car payment, he had to cosign for me to be able to get the car. I don’t like that. I would rather it be Me, Myself and I.”

A young black man with glasses and a scarf, smiling

On the other hand, when I asked Michael if he considered himself a successful person, he answered “I do. I often don’t give myself as much credit as I should, but I do consider myself a successful person.”

Michael Williams is a 28-year-old recently-single black man, living in Chicago after growing up in Englewood. Michael also has some measurable successes to his name. At the time we spoke he had recently completed a short contract with a prestigious design studio, and was pursuing his Master’s degree.

Michael’s definition of success feels noticeably different from Rebecca’s. “A successful person, to me, looks like someone who doesn’t strive to be perfect, they strive to by polished. [They’re a person who] is not where they want to be, but isn’t where they used to be… Success is knowing your strengths, your weaknesses and being able to critique yourself… to say I’m not good at this, I should work on this.” When asked what a successful person looked like, he spoke about his program director. “Her transparency, her willingness to be vulnerable, her authenticity… I think that’s also part of being successful.”

It seems to me that while Rebecca has a very concrete, measurable definition of success, Michael’s was more of a way of being. And as I looked over my interviews, this was a pattern.

Those who considered themselves successful had a “how” type definition of success and those who told me they weren’t successful yet, had a “what”** type definition.

And these groups didn’t seem to be divided by gender, race, socio-economic status… but I’ll write more about the differences next time.

I also asked people to score themselves on a self-reported happiness scale (Lyubomirsky & Lepper, 1999). Michael gave himself a score of 7/7, as happy as you can get, while Rebecca gave herself a 5.25/7. In fact, everyone I spoke to who said they were successful scored a 6.5 or higher, while those who told me they weren’t yet successful scored between 3 and 5.25 (no one scored themselves lower than a 3).

Rebecca, and the other self-declared unsuccessful (remember Chirag? He was in this group too) thought of themselves as less happy than those who were successful. Which makes perfect sense when you take a minute to think through how they define success.

Rebecca’s way lends itself to the sentence “I’ll be successful when…” meaning a future date when she’ll have money, her own house, her independence. She won’t be successful until she gets those concrete things. While Michael sees himself as successful simply because he’s striving to improve and to know himself better. He has goals, sure, but his status as a successful person isn’t contingent upon meeting them.

While Rebecca holds her success dangled in front of herself, like a carrot she’ll never quite reach, Michael can be successful right now, today, and so he can be proud of himself, fulfilled and happy.

But, of course, the picture is not really this black and white. There were times in our conversation when Rebecca’s viewpoints drifted towards the “how,” and when Michaels drifted towards the “what.” So what exactly is it that dictates our lens, and is it in our power to change?

If you’re anything like me, you have about a million questions — some of which I’ll answer. My next article, “Why do some people feel successful and others… don’t” focuses on what makes the Rebeccas different from the Michaels — we’ll look at their childhoods, their relationships with failure, their struggles and their experiences of safety. And in the following article, we’ll explore how you can shift between a “what” and a “how” type definition of success. Stay tuned.

*Rebecca Anderson, Michael Williams and Chirag Bakshi are all pseudonyms to protect the privacy of these people who so kindly, generously and vulnerably shared parts of their journey with us. Other highly identifying details have also been changed, photos are stock photography.

** I wish I could say I came up with this terminology, but it was actually a very clever client

Here are links to all the published articles in this series:

Are you a fraud? Am I?

Is your relationship with success healthy?

Why do some people feel successful, and others don’t?

Fixing your relationship with success… A model and a magic pill (sort of).

Why we self-sabotage.

Holmes TH, Rahe RH. The Social Readjustment Rating Scale. J Psychosom Res 1967;11:213–218.

Lyubomirsky, S., & Lepper, H. (1999). A measure of subjective happiness: Preliminary reliability and construct validation. Social Indicators Research, 46, 137–155. The original publication is available at www.springerlink.com.

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Michelle Krasny

Career Coach and avid researcher, exploring what it means to have a kickass career without sacrificing your soul or sanity along the way: michellekrasny.com