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The Five-Year Cliff

Nobody tells you that you hit a career cliff every five years - here’s how to overcome it.

Robert Greiner
Robert Greiner
26 min read
The Five-Year Cliff

Imagine you’re running a marathon. Months of strenuous training have led you to this moment. As the race unfolds, the initial miles breeze past - each step taking you closer to personal victory. Then, around mile 20, you crash into an invisible barrier known as “the wall” - the moment when your body’s glycogen stores are depleted. Your body screams for relief. Your legs weigh a metric ton. Your mind tells you to stop at all costs. Whether or not you can push through the wall defines your marathon experience.

Much like a grueling marathon, your career is its own long-haul race. You will hit a professional plateau every five years or so - a “five-year cliff” that will unanchor you from your plans and aspirations. Periods of robust growth gradually yield to seasons of stagnation. Projects that were once exciting begin to feel mundane. 

Nobody talks about the cliff, but we all experience it.

I thought being a programmer would be enough to sustain me professionally until I was ready to retire. Until it wasn’t. One day, suddenly, it dawned on me that coding alone wouldn't fulfill me for the next several decades. This jarring realization gave me a sense of dread, loneliness, and rudderlessness. In hindsight, the signs were there - like the subtle warning lights on an aircraft altimeter hinting that I was veering off my trajectory.

Interesting projects felt like routine maintenance checks. I became frustrated at the smallest inconvenience or strange corporate policy. The joy of solving complex problems began to wane. I was going through the motions. The cliff forced me to reconsider my entire career path. I left that job out of frustration, jumping to the first opportunity that offered something fresh.

In retrospect, leaving was the right move, but I did it for all the wrong reasons. Over time, I developed strategies for preparing and overcoming these inevitable cliffs so they aren’t as painful. I needed a way to move forward without finding myself in a situation where I became reactionary.

Cultivate Relationships

Relationships are the invisible latticework that we build our careers around. You simply will not be able to accomplish what you want in life - personally or professionally - without other people in your corner. Surround yourself with trusted colleagues, friends, and mentors who can journey with you through your professional plateaus. Strong connections provide stability. Relationships transform careers from solitary journeys to team adventures.

As I closed the chapter at my first job, I couldn’t help but feel the gravitational pull of uncertainty. I left a fantastic gig with a good reputation in a stable industry. Unfortunately, there was no clear path forward, and after a few years, it was time for something new. Right away, I found myself among a fresh cast of characters. We bonded over our interest in board games: Shadow Hunters, Agricola, and Liar’s Dice were our mainstays. These strong relationships proved priceless when the company started doing mass layoffs to gear up for sale. Friends, it turns out, can be the best life vests in a sinking ship.

Nine years into my career. Two career cliffs. Clockwork.

Build Your Talent Stack

For years, I labored under the misconception that I needed to be the best at one thing to succeed in my career. If I were the best programmer, everyone would respect me and listen to my ideas. But, as I navigated the complex career landscape, I realized I was too one-dimensional. Who cares if I'm the best at my craft when I can't communicate my ideas properly? How much better of a developer did I need to be than everyone else if I annoyed everyone around me? How valuable am I if I can't make the team better because I'm around?

Careers thrive on the accumulation of a wide range of skills over time. Skills build and compound, providing exponential returns on your energy investment. You don’t have to be the best at anything. You just need to be good enough at a bunch of things. Your day job requires various skills to be successful, focus on building those while peppering in skills like writing, public speaking, and people skills.

Seek unique experiences, stretch assignments, training opportunities, and feedback. Careers are shaped through accretion, not maximization. You don’t have to get it right every time; just keep building and let the compounding take care of itself.

Your Talent Stack Compounds Growth

Understand Yourself

Self-awareness is the x-factor for a successful career. It's the secret sauce that transforms an ordinary burger into a gourmet experience. Understanding your quirks and decoding the subtle cues from others can be the difference between tension and harmony. Taking personality tests, diving into your motivations, or showing vulnerability won't just build your emotional IQ - it will demonstrate maturity and provide the seasoning that makes work so flavorful.

Do you skew introverted or extroverted? Do you prefer tight deadlines or loose ones? Do you get fired up working in a group or by yourself? Do you like to dig into details or focus on the big picture?

Sometimes, you have to go backward to go forward. When I took my first job in consulting, I took a pay cut. I was hired a level lower than I was hoping for because my new company wanted to see if I could get up-to-speed on some consulting skills I didn’t have coming into the job. This came as a blow to the ego, but I saw the potential upside in career growth and advancement, so I rolled the dice. Knowing how hardwired achievement is to my brain, I knew I needed to find a place with plenty of room to grow and find a culture that incentivized teamwork and group success so I could let my competitive nature out in a healthy way. Instead of trying to forcefully change my default operating mode to suit my current situation, I found a culture that would let me thrive based on who I already am.

Find a Mentor

When the student is ready, the teacher will appear. -Tao Te Ching

We take for granted how many people pour their life’s energy into our success. Reflecting on my career, I think about the mentors who took me under their wing and never asked for anything in return. I'm a better thinker, communicator, and leader because of some of the early opportunities I had in my career to work with people smarter than me.

Seek out people who have already experienced what you are going through. Mentoring relationships can be long-term partnerships or single advice sessions. Ask questions, follow up, and stay curious. Your ability to extract value from mentors is directly proportional to the energy you put into it.

Some of the most effective mentors aren't accessible to us today. Bill Campbell is regarded as one of the best business coaches in history. All of his experience and wisdom are distilled in the Trillion Dollar Coach. Marshall Goldsmith will help you figure out why you are annoying everyone around you. Dale Carnegie will help you make friends and build lasting relationships.

You don't need access to a mentor to learn their secrets of success. Neil deGrasse Tyson seeks out people with individual attributes he admires to create a super role model.

Take Control of Your Career Journey

Nobody is watching out for your career; taking control of the journey is up to you. Don’t wait for the next five-year cliff to take you by surprise - you know it’s coming. The time to start preparing is now.

Remember, every cliff has a silver lining - a vista where you can see new horizons. Navigate wisely through building exceptional relationships, developing your talent stack, better understanding how you are wired, and engaging with mentors. You may find what seemed like an insurmountable barrier becomes the very vantage point where you plot your next big leap.

Start preparing for your next five-year cliff today by downloading The Career Jumpstart Guide for free. It's one page with actionable and practical guidance and tools to help get you unstuck at any level.

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    Robert Greiner Twitter

    Professional optimist. I write a weekly newsletter for humans at the intersection of business, technology, leadership, and career growth.

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