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  • Writer's pictureBill Holmes

Failing Upwards!

project, portfolio, program,
You have to know what your organization values!

“If we don't see a failure as a challenge to modify our approach, but rather as a problem with ourselves, as a personality defect, we will immediately feel overwhelmed.” Anthony Robbins

“The man who has won millions at the cost of his conscience is a failure.” B. C. Forbes

I have a confession.

Several years ago, I decided I wasn’t interested in getting promoted. That may sound odd, but hear me out. I really enjoy delivering tangible results by selecting talented teams and letting them excel at what they do best. I am also remarkably bored by corporate politics and often find myself avoiding events that are, in theory, “good” for my career. I like to work hard, develop my team and spend time with my family.

Did I mention that my pay is capped? Yep. A “promotion” may appeal to my ego but does nothing for my economic bottom line.

I have been involved in developing senior and executive level employees for years, and I always share with them what I believe is a great piece of advice. I tell them that your career defined by the choices you make, and every choice is a trade off. Are you willing to travel extensively? Then you will miss things at home. Are you willing to relocate? Then you will be placing strain on your family. Do you want to be in a key staff position so you can be in the room when the big decision is made? Then you are signing up for a lot of late meetings.

Any of those choices are fine! But be aware of the consequences. It is honorable and acceptable to choose to not be “in the room”, or move, or travel. But, those choices will make you less desirable as a candidate for promotions. But there are no "wrong" choices. Just don’t get upset when people who make different choices get promoted and you don’t.

I have a colleague who has retired. They have done a nice job of climbing the corporate ladder, but every tale has an end. I was discussing the retirement with someone who said that this person had “never accomplished anything” and that they were a classic example of “failing upward”.

I had never heard that term before, so I looked it up! There are several versions of the concept, but they are all variations of how a “failure” can actually work to benefit someone’s career. It is implied that cronyism or an unhealthy work environment are the root causes.

Maybe. But I believe that what appears to be failing upwards is really misreading the particular skill set of an individual. Where pragmatic and practical people define career success based on what can quantitatively be measured, that is not what many companies use to define success.

Success is not generally measured by what was quantitatively delivered, rather it is defined by the personal relationships that a person has cultivated. That is their skill set! What appears to be “failing upwards” is really a lack of recognition of what an organization really values.

People like to feel good and not have complicated “issues” raised. They don’t necessarily want to hear about flaws in their plans or how someone somewhere in the bowls of the organization knows more than they do. Many organizations face problems that are essentially unsolvable within their allotted budgets, but being reminded of that doesn't make people feel good about themselves! People who are pragmatic and point out these flaws are generally not appreciated.

But what is solvable?

Well, things like vision, planning and initiatives are all fun to focus on. Great sound bites, half the work! Plus, if you can get consultants on board, you get great presentations that someone else did! And, who can really say if anything was actually accomplished? That is analysis that will be conducted by future teams long after you are gone! Meanwhile, everyone will be congratulated on guiding the organization into the future, even if we all know that promised land will never get here.

I was sitting in a conference room a few days ago and I noticed a "road map" poster hanging on the wall. It was part of a huge effort many years and many of the milestone dates have already passed, however almost none of the proposed accomplishments were delivered. Do you think missing all those deadlines had a negative impact on people's careers?


And for the people who are focused on tangible results, these are tough things to come to terms with.

To my colleague! I wish you well in retirement! May you find a job without actual performance metrics! History says you will...


We are preparing for a booth at an upcoming boat show. It is a huge show and will have approximately 80,000 attendees over the course of 4 days, so we want to make sure our display is done correctly. Having never done anything like this, we are composing a list of basics – table, chairs, carpet to stand on, banners, cash, cash box, credit card processing, receipts. It is a huge event for us, but we have never done anything like this before. Wish us luck!


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