The Brutal Career Advice I Wish Someone Had Given Me

Post by The Brutal Career Advice I Wish Someone Had Given Me

Origami is likely the closest thing to real world magic I’ve ever seen. A single colorful square piece of paper precisely folded turns into a beautiful crane. Pure magic -- only to be outdone by middling talent getting three promotions every two years.We’ve all had colleagues like this. They seemingly get promoted too quickly, too often, or both.

From the outside, my career success was pure rocket ship. The truth is that my career success was more barbell shaped.

After getting into tech, I was promoted twice in my first 18 months, ultimately landing as a sales manager. The next six years were the long shaft of the barbell: the worst year of my career followed by a litany of career management mistakes.

At one point I was the top performing channel sales manager globally for two years in a row and watched others be promoted ahead of me. It would be easy to suspect that I had a character flaw -- too often the case with sales leaders -- if it weren’t for the extraordinary success I enjoyed in the coming years. Sadly, I mismanaged my career for years while I repeatedly stacked up top performances and awards.

The last few years of my career as Country Manager were filled with far more ups and downs, but suddenly I had more trust, respect, admiration, and responsibility than ever before.

I finished my corporate career leading a $50 million dollar business that would go on to continued success without me.

What follows are three key lessons I learned from years of career mismanagement. These concepts are not just my own. They have been tempered, forged, and strengthened by observing hundreds of my direct reports and colleagues. I believe they are universally applicable to everyone’s career. I wish someone had told me these things a long time ago.

Ask For What You Want

My career plateau is the direct result of never explicitly asking for what I wanted. I was the equivalent of the quiet Road Runner winning races without any particular aim. I suspected each of my bosses knew I wanted to be a director and segment leader, but I failed to illustrate that in detail with timelines and specifics.

“If you don’t ask, you don’t get”

Stating the obvious, asking for what you want is not difficult. Fearing the answer is.

Think of asking for what you want as a starting point to a long journey ahead. Asking for a promotion is not the final boss fight with Boswer, but rather the starting point.

And if you’ve been brave enough to state your explicit career aspirations, this is likely where you will falter on your path to promotion. The trouble is that when we ask others for anything, we wrongly transfer ownership of our happiness into their hands, expecting them to deliver us expedient joy. Bosses don’t do that.

You’re likely to have surprised your boss with your request and they will politely tell you no in a myriad of ways. That’s ok. Don’t be discouraged.

Ask your boss and others for feedback on what you need to improve. Then come up with a plan to make it happen.

It’s not your boss’s responsibility to help you get what you want. That’s your job.

Perhaps you need to read some books, live on Youtube (productively) for the next few months, get a mentor, take a class, or build your network. Those are all possible solutions, but none of those need to run through your boss.

While you’re improving yourself, continue to have monthly conversations with your boss about what you want. These talks will help you co-create a path with your boss.

Make sure you document the skills that you are missing, improving, and what good looks like. And don’t forget to push for timelines. You want to be crystal clear with your boss that if you can do ‘X’ skills by ‘Y’ date then you’ll be in a good position to be promoted.

“If it’s to be, it’s up to me.”

Do The Right Thing

This one lesson drove the greatest part of my success. I learned it from a wristband.

Halfway through high school, I changed schools to play on a better basketball team. Half of the team was just like me: new to the school and team. In order to help us grow into a unit, our coach and his wife gave us homemade wristbands that said DTRT. We were sworn to secrecy not to reveal what it meant. It was our bond, our union -- a small token to symbolize the kinship and sacrifice that would be needed for us to go to win a championship. It was the only championship team I’ve ever been part of. The lesson has lasted decades.

The ultimate success of any team or business is tied to how its members function together. Cooperation is a greater factor of success than individualism -- despite what popular culture tells us.

It should be no surprise that executive teams are the folks that are able to cooperate and work together better than other employees. They continually DTRT and solve for the company’s success over their own success.

Put the company’s interest ahead of your own and you will be rewarded as others fall away when they fail to do the same. Without a doubt this is a long-term strategy, but it’s the only lasting career strategy.

A Note About Hard Work

I don’t want to suggest that if you “ask for what you want” and always “solve for the company” you will rocket yourself to any promotion.

You have to get results.

And most people don’t don’t work hard enough to get results and their promotion.
Let’s say you work at a tech company and the average employee works 50 hours a week. If you are putting in the same 50 hours, are you working hard?


You must work at least 10% more hours than your colleagues until you are obviously the best at what you do. In our example above, that’s one extra hour per day.

If you’re unwilling to do that, you’re gambling with your career. You’re wasting 50 hours a week just to keep your job when five more hours will likely improve your whole life.

Most people that are frustrated with their careers only need to put in a little bit more effort to stand out.

It’s a Journey

I wouldn’t trade my barbell shaped career for anything. I’m grateful for all that my mistakes have taught me. Remember, it’s a journey and there are no precise and perfect origami diagrams to help you build your career. You have to create it on your own and “asking for what you want” is just the beginning.

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Dave Shepherd

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