Moving beyond your success

Rainey Reitman
11 min readOct 30, 2016

A few years ago, I had a conversation with an acquaintance who introduced me to an idea that blew my mind: the very things which made someone successful early in her career could prevent growth later in a career.

Wait, what? How was that even possible?

My acquaintance suggested I read What Got You Here Won’t Get You There by Marshall Goldsmith with Peter Reiter, which I recommend to any successful person who feels like she’s inexplicably plateaued. The concepts in the book influenced my thinking on this issue, so I mention it now to give due credit. However, my ideas diverge from the author’s in a number of key ways. For example, one of the main ideas of the book is that successful people are successful in spite of certain qualities which later limit their growth. I actually tend to go a step further: sometimes, successful people may be successful because of certain qualities that later limit their growth. So think of what follows as my personal interpretation of certain ideas first introduced by Goldsmith, not a summary of the book.

One idea that stemmed in part from the book is that successful people often suffer from delusions about why they are successful.

The Why of Success

Imagine a man putting on a pair of brown shoes on Tuesday, walking down the street to the gas station, and buying 3 five dollar lotto cards. Imagine he wins a few thousand dollars. He comes in again every few days, playing a range of different types of scratch cards, not winning. (Yes, it happens: my first job out of college was at a gas station and I had a lot of repeat customers for lotto cards.) And then one day he wins more money, again while wearing those same brown shoes, playing five dollar scratchers, on a Tuesday. All of a sudden, he’s got a pattern that seems successful: shoes, five dollar scratchers, Tuesdays, this gas station.

Of course, he’s wrong. But humans love patterns; our brains seek them out.

Highly successful people may have used a wide range of techniques to generate early successes in their careers. But successful people can fall into the same trap as the lotto playing guy: it feels like there’s a connection, there are facts and data and positive outcomes, but they’re still totally wrong about the why of success. Success could have been coincidental, or it could have hinged on factors you aren’t considering.

Other times, successful people use techniques that directly and transparently impact the successful outcome. The example that comes to mind is a woman who asks for more during a salary negotiation and is rewarded with a higher salary from a boss who would never have otherwise considered it. We don’t know exactly the root of the success — was it how she asked? Or was it simply that she asked at all? Were there other ways to negotiate for more money that would have been even more successful? But we know that there was some relationship between this action and that outcome. She created a success, and future successes may lock her into a set of beliefs about how successes are created.

Sometimes we overestimate our own contributions. We may believe a success came as a result of a specific technique or skill, when in fact the same outcome could have been brought about through other means. We become rooted in a particular pattern of behavior or thinking, unable to differentiate between those factors that have an influence on real success — like deciding to speak up in a salary negotiation — from those that are coincidental — like wearing brown shoes and buying lotto cards only on Tuesdays.

Worse, we may even try to apply these coincidental techniques to situations that are completely unrelated. Think: the lotto guy wearing brown shoes to a salary negotiation.

We may begin to believe that patterns we associate with certain successes — which are actually unproven theories — will work to create successes in wholly different circumstances. I think of this as superstition of success.

How Superstition of Success Holds Us Back

Patterns can become deeply rooted in our psyche. You may even begin to believe that characteristics you associate with your successes are unchangeable characteristics of your personality.

And that’s risky. It creates blind spots in our own lives and could prevent us from developing skills and traits that would provide necessary balance to skills we developed early in life. These imbalances can end up holding people back in ways that can be hard to recognize. Let me sketch out a few potential examples — based on real people I’ve encountered over the years:

A man early in his career demonstrated tenacity, boldness, and a tendency to speak out directly. People gravitated toward him and considered him a natural leader. But as time went on, people he worked with began to see him as unyielding, too quick to act without considering all the facts. Coworkers thought he was a poor listener. When a senior role opened up in his organization, he was never considered; everyone assumed he was too bull-headed and unyielding to be elevated into a role requiring subtlety and care. Perhaps worse, he had no idea. He believed that his tenacity and boldness were exactly what had made him so successful up until then. And in fact, he believed they were indelible facets of his personality: that he was a bold, visionary man who would tell it like it was and stick to the end goal.

Whether or not he was right that these characteristics had contributed to early successes, these habits had stalled his career in ways he couldn’t imagine. Unable to move ahead in his current organization, he simply went to another organization, where his no-bullshit communication style and commitment to achieving results dazzled new coworkers all over again, which reaffirmed his belief that these qualities were necessary to achieving success. This set him up to stall out in exactly the same way, a pattern he could repeat as often as he’d like over the course of his career.

Now take a senior executive who is liked by almost everyone and considered a conscientious listener. She works long hours, often taking on overflow work so that her employees can go home at the end of the day. Everyone adores her. She considers herself a deeply compassionate and caring person, and she considers those characteristics unchangeable features of her personality. But she keeps losing her best people because they aren’t challenged or given chances to grow. In her efforts to protect employees from the most difficult work, she’s robbed them of opportunities to take on difficult challenges and stretch their wings. Ambitious employees hungry to prove themselves gravitate to other organizations where they can be at the center of things, and the employees that remain exploit the woman’s generosity and kindness, knowing that she won’t ever fire them. The executive finds that the only way she can grow her organization is to simply heap more work upon her own overburdened shoulders, until she is so exhausted her health begins failing.

These aren’t just hypothetical scenarios: I’ve met more than one person who fits each of these models. In fact, I can think of three people who fit the first scenario pretty specifically, and two people who are a pretty exact match for the second — dismal outcomes and all!

12 Bad Habits of Somewhat Successful People

Goldsmith outlines 20 “transactional flaws” in his book, basically bad habits of interpersonal behavior that successful people often adopt. These are the type of habits that successful people may employ early in careers — intentionally or often unintentionally — which ultimately limit their growth.

There are about 9 of these “transactional flaws” that I see frequently among highly successful nonprofit professionals (descriptions excerpted from Goldsmith’s book):

  • Winning too much: The need to win at all costs and in all situations — when it matters, when it doesn’t, and when it’s totally beside the point.
  • Adding too much value: The overwhelming desire to add our two cents to every discussion.
  • Passing judgement: The need to rate others and impose our standards on them.
  • Speaking when angry: Using emotional volatility as a management tool.
  • Withholding information: The refusal to share information in order to maintain an advantage over others.
  • Claiming credit that we don’t deserve: The most annoying way to overestimate our contribution to any success.
  • Clinging to the past: The need to deflect blame away from ourselves and onto events and people from our past; a subset of blaming everyone else.
  • Playing favorites: Failing to see that we are treating someone unfairly.
  • The excessive need to be “me”: Exalting our faults as virtues simply because they’re who we are.

To this list, I’d add a few I think are special favorites among nonprofit professionals:

  • Acting like a martyr: Inflicting self-suffering to complete work in an unconscious attempt to garner sympathy, social credit, and admiration.
  • Indecisiveness in the name of consensus: Allowing even small decisions to grow into time-sucking debates, often accompanied by a belief that absolute consensus must be achieved on all issues or that every decision benefits from a popularity contest.
  • Unproductive kindness: Rooted in a deep desire to be liked by others, this can result in nonprofit managers refusing to have hard conversations, make unpopular decisions, terminate employees that are not working out, and do any number of other things to be liked by all parties. They may even pass these hard decisions on to other managers.

Sometimes it’ll be easy to look at a list like this and immediately see which characteristics apply to your own professional life. Nobody is perfect, after all; it’s impossible to be the perfect, compassionate, honest communicator every moment of every day.

But I think that often we really don’t know how we come across. We may have a personal narrative about our lives that is wildly different from how we are perceived by coworkers. You may consider yourself a hard-working, well-liked, efficient, and direct manager, while others see you as brusque, a brutal task master, playing favorites, and impatient.

The first step is getting to the root of how you are perceived by others and then use that to tease out what bad habits, transactional flaws, or unintended messages you may be conveying.

A good starting point is listening.

Don’t Flinch: A Self Assessment Tool

One way to start unravelling our own self-limiting habits is to pay meticulous attention whenever someone describes you. Hone in on the exact words, and try to note them without judgement or defensiveness. I’d even advise collecting them in a notebook or document of some form, so you can look for trends over a week or two.

You should also ask people to give you feedback — what do I do well? What do I need to work on? It’s worth asking this of people you know well as well as those you know pretty casually; sometimes a casual coworker will have insights our closest coworkers are blind to. It’s OK — in fact, it’s very illuminating — if this list is substantially different from how you see yourself.

Once you have a good list, try to stretch yourself to imagine what might be missing.

Are you making trade-offs along the way to success? Do people see you as a caricature of how you see yourself, honing in on the most obvious traits and not seeing the other components of you? Have your successes come with interpersonal costs, or with personal ones?

Occasionally, people will be very blunt in their feedback. “You’re impatient and you never listen to other people,” a coworker might tell you.

Other times, the feedback will be couched in much gentler terms. You may have to spend some time searching for what the underlying message is. You may hear that you have high standards, get the job done no matter what, or are always nice. And deep down, these same coworkers may think that you judge everyone by your standards, are an obsessive workaholic, or have no backbone.

It can be useful to actually make a chart of the qualities you associate with your success or that people associate with your successes, and then stretch yourself to imagine what might be missing. For example, your list of personal success qualities might looks something like this:

  • Always delivers projects
  • Meticulous
  • Likeable and kind
  • Busy

Nice characteristics, right? It’s easy to see how we might think these characteristics are important and even necessary to success. But let’s tease out some of the hidden possibilities for how a seemingly positive characteristic could be interpreted by others, have unintended negative consequences, or can lock us into habits that limit growth. I’ll call these negative characteristics “shadow qualities” since they often lurk in the shadow of the very qualities we associate with success.

Quality associated with your prior successes:

Always delivers projects

Potential shadow qualities limiting your growth:

  • Willing to sacrifice anything to get a project done, including burning yourself out
  • Willing to run over others to deliver the project on time
  • Judgmental of others who are less productive
  • Not ambitious; unwilling to reach for stretch goals whose results are uncertain
  • Convinced on your own perfection and the necessity of your own contribution; egotistical

Quality associated with your prior successes:

Meticulous

Potential shadow qualities limiting your growth:

  • Unyielding
  • Micro-managing
  • Unwilling to share in responsibilities
  • Judgmental of the shortcomings of others
  • Certain you know the one true way of doing things
  • Self-hating; unable to live up to your own standards
  • Creating anxiety among those around you
  • No fun

Qualities associated with your prior successes:

Likeable and kind

Potential shadow qualities limiting your growth:

  • Unable to make hard decisions
  • Unable to have frank, difficult conversations
  • Always available as a support for someone else, even when it inconveniences you
  • Unwilling to make unpopular decisions — or sometimes even seriously consider them!

Quality associated with your prior successes:

Busy

Potential shadow qualities limiting your growth:

  • Unavailable
  • Can’t see the forest for the trees
  • Constantly chasing unachievable goals
  • Burning yourself out
  • Skeptical of the priorities of others
  • Distant from coworkers

To do this exercise well, it’s imperative to stretch your imagination a bit. The point is to try to tease out potential blind spots and trade-offs you’ve been making unconsciously. The shadow qualities might be very uncomfortable, full of things that you’d even reject at first blush.

Do it anyway. Sit with the idea that you’ve lost something in the pursuit of success, and this is the first step to starting to repair it.

It may help to walk away for a few days and come back to this list with fresh eyes, and ideally getting feedback from a few other people about whether any of the “awfuls” in the chart could apply to you.

Not every shadow quality you brainstorm will apply to you, of course. Thankfully! But probably a couple of those uncomfortable traits on your list will ring true for your own life.

Now What?

If you’ve been successful in your career, it can be easy to find yourself trapped in certain ideas about why you were successful. Too often, those ideas are based as much on superstition as on fact. In turn, these ideas about success can limit your growth.

The good news is it doesn’t have to be that way. It is possible to build a new set of habits and move beyond the characteristics that defined you early in your career.

Awareness is where we start. But then it’s time to delve into the real work. Healing troubled work relationships and reinventing yourself is hard, time-consuming work. I’m not going to attempt to cover that process here, but I would recommend Goldsmith’s book as a starting place, though I consider his prescription for change most appropriate in the most dire of circumstances. And if something in this article resonated with you and you’d like to start tackling these imbalanced in your career life, please contact me about coaching.

Finally, I consider this article to be a working document with my current thoughts on the matter, and I recognize that there are a range of views and experiences beyond my own. I’d love to hear your experiences, thoughts, and ideas. Please consider leaving me a comment below or send me an email if you have thoughts to share.

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Rainey Reitman

Writing on personal privacy, government transparency, nonprofit leadership, and whatever else intrigues me. Views are my own. EFF/Groundwork Consulting/FPF.