The Slack message was genuine and brief, “congrats on 20 years!” My name had apparently been listed on a slide during the quarterly all-hands meeting of our business unit, along with roughly a dozen other employees who had spent 20 years of their lives working at Adobe. In the interest of time, only the 25 year anniversary recipients were mentioned out loud. Most folks did not notice my name, as I heard from only one person. Heck, I didn’t even notice since I was busy and unable to attend. One vice president noticed. He saw me from a distance a couple of days later as we approached each other down a long Seattle hallway.

“Congrats on 20 years,” he started as we reached shouting distance. “Too bad you couldn’t find the time to make the meeting,” he said as we closed to within a few feet. “Twenty years is a long time. Sounds like a rut. You should get that looked at,” he finished as he walked by.

Welcome to the tech sector, where longevity has become some combination of freakish curiosity and career sin. These companies are fighting battles against high turnover, and exorbitant replacement costs of somewhere between 1–4X the salary of an experienced senior manager [1][2][3]. Yet, their cultures often work against their better interests by discouraging stability.

I know this VP well. He was at least partially joking. One of the things I enjoy about working with him is he is not afraid to say what others are thinking. A slap to the face is always preferable to a knife in the back. His sentiment was not new to me. Somewhere around the ten year mark, my Adobe work anniversaries morphed from a badge of honor into something more like a scarlet letter.

Fighting stagnation

Our Senior Vice President back then was David Wadhwani (of AppDynamics fame). It was 2012, and he was overseeing a reboot of our multi-billion dollar Creative Suite product line into what would become a massively successful cloud-based subscription business now known as Creative Cloud. I was a Director of Product Management, working on Creative Cloud, and also a member of the Adobe Seattle Site Council. That led to a number of conversations between Wadhwani and I.

He told me he was taking aim not only at our aging boxed software business, but at our too-comfortable culture. He identified a prevalent mindset with employees who were working more to secure their jobs than to take the risks necessary to forge a bright future.

These were the folks who would listen intently at employee meetings for the names of the projects or products that executives mentioned, and then eagerly try to find safe passage aboard what they now perceived to be safe areas of the company. These were the folks who were experts at knowing how to run the business exactly as it was, and fought change like antibodies repelling a toxic substance. They would use their longevity to shout down new ideas because they had already been attempted and failed, even if the attempts had come years earlier with different people and circumstances.

Wadhwani knew the culture had to change in order to create a fertile environment for innovation. A long tenure at the company now meant more scrutiny, not less. People needed to prove they were ready to embrace new and different, instead of fighting to preserve status quo. Fresh faces and perspectives were often valued over experience. This was not unique to Adobe.

“It used to be that when you were looking at someone’s resume and they changed jobs more frequently than every five to seven years, they’d be labeled as a job hopper, unstable, greedy or selfish, unable to hold a job. Whatever it was, it usually flagged them and pulled them out of the stack. Now, in some regards, I think it has flipped. Now when recruiters look at someone who has stayed in a role for more than three years, the question is why? What have they been doing? … The world is changing really fast. There’s this intuition that if you’re doing the same job for more than three years and your job didn’t change, that means either your company’s not that dynamic or you are not that dynamic. I’m not saying that’s always the case, I’m just saying there’s this increasing perception” — Jobvite CEO Dan Finnigan, in a 2011 interview

The dynamic agitated many vets. No longer could they count on past victories to propel them forward. Like bees whose hive had been disturbed, they became hyperactive. Some would commute from San Jose to San Francisco just to sit near Wadhwani and his staff. Some paid more attention to how they dressed to project a younger, hipper, image. Others were unmoved, staying their course. Nobody was entirely free of the disarray caused by the transformation.

I loved it. As someone who cared deeply about Adobe, it was clear we were at risk of allowing innovator’s dilemma to slowly asphyxiate our business. I saw Wadhwani as the catalyst the company needed. Change was not something I embraced when my career started, but adaptation and anticipation quickly became second nature. My appetite for change did not come from lack of attachment to Adobe history. To the contrary, it was fueled by a deep loyalty and dedication to our mission built over many years.

Distilling wisdom from experience

We met in college. It was December, 1996. President Clinton had just been elected to his second term. Grunge was fading as the Spice Girls were rising. The Nintendo 64 had just been released in Japan to much acclaim, Microsoft had launched Windows 95 just over a year prior, and Netscape Navigator owned 85% of the browser market. The economy was booming, fueled by technology. My time at American University in Washington D.C. was coming to an end.

I was cocky in the way newly minted 21-year-olds often are, with all the answers to none of life’s difficult questions. My then-girlfriend-now-wife and I were visiting Seattle on our winter break looking for potential jobs as graduation loomed. Adobe was a tech tween. The dust was still settling from their acquisition of Seattle-based desktop publishing giant Aldus three years prior. I strode into their funky and spunky downtown Seattle office hoping to make an impression.

The beginning

Six months later, I was using a plastic packaging sheet as a shower curtain in my Fremont apartment, while getting ready for my first day as a Technical Support Engineer for Adobe PageMaker. The $30k salary they were going to pay me to answer calls about a product I barely knew felt extremely generous.

Even though school was now officially in my rearview mirror, it felt like my pace of learning had never been greater. Orientation introduced me to 401ks, compound interest, stock options, stock purchase, and healthcare. My job training required me to not only learn the features of the product, but the publishing industry problems they were meant to solve. Kerning, tracking, and CMYK separations, oh my!

I can still remember the sinking feeling when a call would come in and the pre-recorded voice would announce the caller was an Adobe Service Provider. Those were the people who worked at print shops and knew the product inside and out. They were calling me for help. Fake it until you make it was ingrained in me early on.

But I did not have to fake it for long. A reluctant student most of my life, I had a voracious appetite for learning what I needed to master my job. I pestered co-workers with questions, started an unsanctioned new hire training group where we taught each other new concepts we had been introduced to, and even read the dense 500-page PageMaker manual multiple times. An early career highlight was seeing “Adobe Certified Expert” printed on my business cards, even if I had no practical need for business cards at the time.

John and Chuck receiving the National Medal of Technology and Innovation

Adobe used to offer PostScript training to any employee who was interested. After a few dozen calls about PostScript errors, I decided I wanted to learn more about it. What came along with the technical tutelage was a history lesson of how our founders, John Warnock and Chuck Geschke, had built the entire business on this programming language.

They initially tried to sell it as part of a printer, but found that what their customers — including Steve Jobs at Apple —really wanted was the language driving the printer. Geschke and Warnock quickly changed their business plan to center on licensing PostScript, and ultimately sparked the desktop publishing revolution.

PostScript led to the development of Adobe Illustrator, and Aldus used it as the underpinning for PageMaker. Eventually, PDF was created as a derivative of PostScript. That innovation helped Adobe retain and even grow in relevance as the Internet brought the rise of email and electronic documents.

There were so many lessons to be learned about business, and innovation, and Adobe’s culture that proved invaluable for anticipating where the company might go next. But I was building more than knowledge. Deep and lasting personal relationships were forming with my fellow new hires and the standout veterans on my team.

The lightness of living through our 20s with a steady income was not lost on us. We would regularly go out for drinks and dinner after work, or stay late playing video games like Duke Nukem over the corporate network.

Some of happiest memories were spent laughing with friends at work staring at this screen

Everyone on our team became a character in a daily sitcom. There was the narcoleptic woman who would snore during team meetings, the gruff leather-wearing rebel who would ruffle feathers, and the manager who never actually said anything of substance who left us deciphering his manager-speak after each one-on-one. It would prove to be too good to last.

Do not gather moss

The layoffs started about a year after I arrived. The first round included the snorer and some other lesser performers. The next round started cutting more deeply. I distinctly remember going with some of my coworkers who survived the second round of layoffs to see Office Space, and laughing so hard at the perfect satire that I needed to watch it again because I missed so much. Tension had been building so much leading up to the moment we were each called into our manager’s office to receive the good or bad news, it was cathartic to find humor somewhere.

I was beginning to learn the lesson that stability and longevity were not necessarily symbiotic. The ground was shifting beneath my feet. Standing still was only going to mean I would eventually fall.

After almost two years of listening to customers complain about the shortcomings of the product they sometimes called, “RageMaker,” I decided to take a new role in quality engineering on a project codenamed Shuksan.

Shuksan was being built to supplant PageMaker. I spent my first six months exorcising my tech support demons by writing more bugs than any other tester. We would soon launch Shuksan under the name Adobe InDesign.

Just about that time, the rest of the level two tech support team I had worked on were let go or reassigned. It was easy to see it coming despite efforts to conceal the plan. A senior manager had gathered those of us still around after the second support layoff and said, “I know many of you are waiting for the other shoe to drop.” He then took off his shoe and dropped it. “There it is.” He was let go as part of this final reorganization as well.

I had managed to convince some of my closer friends to jump ship with me to quality engineering before the ax fell. We knew we had to pedal faster and keep our eyes open to stay afloat. Adobe was a great place to work, with super nice people, but it was no free ride.

Some of us decided to expand our skills. One of my best friends and I took a series of programming certifications (C and C++) at University of Washington, which allowed me to start automating some of my tests. InDesign was evolving as well.

Finding the impossible is possible

We were taking on an entrenched competitor in Quark XPress, but one with a rather terrible customer service reputation. There was an arrogance that came with their market position that would ultimately be their downfall. InDesign innovated at a pace that made Quark look like it was standing still. Throw in the fact that a customer could get InDesign and Photoshop for roughly the same price as Quark, and it becomes clearer how that industry titan could fall in just a couple of years.

Inertia often provides a false sense of security, as Quark found out. As the great John Wooden once said, “Never mistake activity for achievement.” To that end, I continued adding new programming skills. I started building relational databases and picked up some web development scripting languages like ASP.

I applied for two jobs, and got both of them. One was in developer support, where I would go more deeply into product engineering. The other was as a web developer for internal sites and systems. Both were at Adobe.

Right around this time, the dot com bubble was expanding rapidly. People were leaving the company left and right to chase IPO riches. Usedbooks.com was particularly aggressive at trying to poach people on the InDesign team. My manager was among the people who left. Almost none of them cashed in.

The bubble burst and many were left hoping they could boomerang back to Adobe. Unlike the startups of that era, Adobe had grown on real products being bought by real customers with real money. I would read the newspaper everyday trying to decipher why these companies without any profit or meaningful revenue could be valued so highly.

You can’t fake real value. At least, you can’t fake it for long. The market knows it. Your employer knows it.

Before making a decision between the two roles, my manager warned me to be careful. He said that the company would take everything I would give it and ask for more. His words struck a nerve as I had recently become a father and was committed to never letting work keep me from my family. Standing still, though, was not an option. I had already learned that lesson.

Lady luck plays her role

I wound up taking the web development job and loved it. I thought I had found my calling until another layoff came, and my position was eliminated. These layoffs had become an annual Fall occurrence to cull the herd. My manager walked in and told me a I was a program manager now…for Adobe PageMaker.

With the rise of InDesign, engineering for PageMaker had been moved to India, so most of my meetings were at 6AM or 9PM. Two of the smartest and most productive people I have ever worked with, Jo Ann Buckner and Laurel Hahn Zimmer, were my product management and product support partners, respectively.

They taught me about product development from a different lens. We needed to define roadmaps, plan major milestones, and communicate our plans effectively, both to the team and to the execs.

I was forced to learn about Gantt charts and Microsoft Project. I used some of my spare time to learn about Microsoft Project Server, mainly so I could store schedules there and then dynamically share the milestones through the internal website system I had built in my previous job. That was pretty novel in 2004.

As luck would have it, that side project wound up leading to the biggest break in my career. Adobe announced they were acquiring web giant Macromedia in a $3.4 billion dollar deal. A dorky looking guy in glasses — not exactly a rare breed in tech — named Hans Grande knocked on my office door and asked if I knew anything about Microsoft Project Server. I nodded. We spoke about it for some time, and then he said, “Come with me.”

We walked into my manager’s office and Grande explained to my manager that the acquisition team was going to need some of my time to help consult. Apparently, the corporate development group had spent some money on an acquisition management system built on top of Project Server, but nobody in the company had any experience with the technology, except me.

Down the rabbit hole

What started as a few weeks on loan, quickly became an offer/request/plea to remain on the project until the deal closed. Most of each week would need to be spent down in San Jose without a clear end date. I would need to enter the clean room, which meant that if the deal was dissolved for any reason, I would not be able to work for either Adobe or Macromedia because I would have been exposed to sensitive information from both companies. We had just had our second child as well.

It was a major decision. My wife and I took more than a few long walks discussing the implications. She was far more encouraging and bullish. I was more reticent, worried that this would be the moment the company took too much of me away from my family. The opportunity proved too unique to pass up. We decided to go for it.

The deal took seven months to close. During that time, I spent many of my days with the top executives from both companies. There was a dizzying amount of talent. Stephen Elop was the Macromedia CEO, before moving on to lead Nokia and then become an EVP at Microsoft. Kevin Lynch was being groomed as a CTO, before he moved to Apple to lead the Apple Watch. Tom Hale was leading a division, and would go on to run product for HomeAway, and now is a President at SurveyMonkey. Dave Mendels was leading a different division, and went on to become CEO for Brightcove. The list goes on. Wadhwani was more of a lieutenant than general at that time.

That experience opened my eyes to how the sausage gets made. All my naive conceptions of how executives always knew what to do were shattered. What I saw were incredibly smart people spending most of their time trying to do what they believed was right for the company, and the rest of their time engaged in political jousting with other executives who were fighting for investment and visibility.

Reconnecting with what matters most

All I knew was product development until that point. Now I was learning about sales, marketing, finance, human resources, and corporate strategy. It was an MBA-in-a-box. I was having the time of my life until I received a call from my wife about four months in, telling me that the doctors had found something wrong with our youngest son. He was developmentally delayed across the board. We would later find out he would have special needs the rest of his life.

A few months later, Grande, who had became one of my best friends over the course of the deal, told me he had been diagnosed with stage four cancer. He was set to be married right around when the deal closed. He went on his honeymoon. Not long after, he passed away.

I would go on to get promoted twice in short succession, becoming a Director of Program Management less than ten years after I started answering tech support calls, but I would never look at career growth the same way. I became wary of moving any higher up in the organization and losing touch with the people I loved.

Where I had once been seduced by the corporate climb, and the thrill of reaching my limits before pushing past them, I now saw it as a game that could not be won. It was a treadmill set at an ever-increasing speed. I chose to step off and run my own trail instead. Title, money, and visibility were the bait I no longer craved. I looked for big projects with great people where I could clearly see how I could make an impact while retaining control over my time.

When I was asked to run product integration for the $1.8 billion dollar Omniture acquisition in 2010, I agreed only after understanding there would be no clean room and more control over my travel schedule. When I was asked to take over product management for the design segment, our largest customer segment that included products like InDesign and Illustrator, I accepted only after knowing there would be opportunity to advance our strategy in the Seattle office so I could spend more time at home.

My misstep came when I violated this newfound principle. I was asked to lead product management for what would become Creative Cloud. I knew it would involve more travel. The responsibilities and team were not crisply outlined. Big mistake.

Only a few months in, it became clear I did not have the resources or authority required to execute on the strategy I knew we needed. I was miserable for the first time in my career. The two fabulous people I had hired to build the face of Adobe’s next-generation product line were helping to craft a terrific vision, but we had no engineers to build it out. Leading the team with dignity through that was excruciating. It felt sleazy to imply purpose where I knew there was none. I had tried to build my career on integrity and doing impactful work on impactful projects. Now, I felt like a phony collecting a paycheck.

Not only that, I felt like a hypocrite. That cultural change Wadhwani was championing, and I was cheering, was predicated on eliminating bloat. My job was safe. The reputation I had built in the years leading up to this point meant I had plenty of runway to work with, but coasting was not my thing.

I had just passed the 15 year mark at Adobe. As much as I supported what Wadhwani was trying to do, the company had over-rotated on valuing fresh faces over people with experience. It felt like it was finally time to move on.

I began aggressively interviewing outside the company. Two offers stood out from the rest. My old-fashioned dream of working for one company my entire career was not meant to be.

Prior to accepting one of the offers, a friend in HR got wind of what was happening and convinced me Wadhwani would want to know. I was skeptical, but I had a meeting already scheduled with him, and was willing to tell him. The moment of truth arrived:

“David, I wanted you to know I’m close to accepting a role outside the company,” I offered. He was surprised, but said without hesitation, “That’s not acceptable. Would you at least be willing to talk to a few people internally if I set up the meetings?”

I felt valued. Not because he offered me money or a new title, but because he demonstrated an understanding of what I brought to the company and was offering to spend his valuable time helping me find my place. I was ready to leave the company I loved and the colleagues who had become some of my closest friends because I could see the music stopping soon and there were no seats I wanted to sit in. Wadhwani stopped the music, knocked the chairs aside, and pointed me in the direction of some seats I had not noticed. I will forever be grateful.

One of those seats was with Paul Gubbay, a VP who had an engineering team developing a technology that was in need of some business focus. I shared a product pitch that aligned very closely with where they were hoping to take their project. Kismet.

I passed on the other jobs in favor of joining the Project Luca team. Luca was eventually released as Adobe Slate, and became just the second product in Adobe history to be named Editor’s Choice by the Apple App Store.

Slate was the second in a new breed of applications being developed by Adobe, meant to reach new customers who were not creative professionals, and did not have the time or desire to learn pro tools. The plan was to bring these applications together under a new brand, and give regular folks a creative system that would help them stand out. Adobe Spark was born.

Spark was everything Wadhwani had wanted when he imagined Creative Cloud. It was mission driven, and used enthusiastically by students and nonprofits alike. It was fresh and fun and built from the cloud up.

He never got to experience the launch of his favorite project, as he accepted his new role as CEO of AppDynamics, but that worked out pretty well for him.

I now run product management for Spark. Our ambitions are grand. The team is fantastic. We are just one year removed from our launch, and are driving product and cultural innovation within Adobe. This could very well be my last and best project at the company.

If this is a rut, I should have driven into a ditch years ago.

Patronizing pernicious perceptions

All told, I have had eleven jobs in my 20 years at Adobe. My experiences have given me a 360 degree view of the business. I was there when InDesign, Creative Suite, Creative Cloud, and Spark were born. I was in the middle of the two largest public-to-public acquisitions in the company’s history.

My regrets are minor, and none of them include my decision to stay at one company for my entire tenure.

Some folks are a little embarrassed to work at an older tech company like Adobe. Not me. That startup everyone is so excited about? Chances are they are using Adobe products to help build it and market it.

People wonder if I stick around because I have no other options. I could have jumped ship dozens of times over the years. Many of the interviews I turned down were for jobs that would have paid me much more than I make right now. Deciding to stay was not about inertia or fear of change. It has always been about the project, the people, and the potential for impact.

There are undoubtedly people who stick around their company for too long, and do it for unproductive reasons. There is good reason to till the fields now and then to allow fresh crops to grow. But consider the mighty oak or the towering redwood. They could never grow to great heights without establishing deep roots. Moving them could very well stunt their growth and destabilize the ground on which they stood.

Other fields, like academia, have learned the value of encouraging depth of study over a lifetime. The tech sector is based on the belief that tomorrow will be better than today. Anything that even resembles stagnation is antithetical to the core value system that fuels our industry.

Longevity, however, need not equal stagnation. It can mean wisdom, passion, dedication, and sustained peak performance. That is what I see when crossing paths with most of the other marathon runners at Adobe.

Wisdom is hard to come by. Companies should treasure it. They should encourage it. They should celebrate it. It just may keep them from getting stuck in a rut.