Chamber 🏰 of Tech Secrets #20

Should you job hop every ~2 years?

The Chamber 🏰 of Tech Secrets is open. Is it a good idea to change jobs every 2 years? Is it a good idea to stay in the same company for a long time? Let’s dig in and explore.

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Job Hopping

I have worked at Chick-fil-A for ~19 years. People tend to be impressed that I stayed with the same organization for so long. By my perceptions from observing LinkedIn profiles and resumes for candidates I interview, it is exceedingly rare. I am not sure why. The default in tech (and sales) tends to be to move every two years or so. Let’s ponder the benefits of changing jobs vs. sticking in one place for a long time.

Benefits of moving around

As I mentioned above, I have been in the same organization for 19 years, and I do not have a history of job hopping. This section is not about my personal experience, but rather my thoughts on the idea from observing others. What are some of the key advantages of changing jobs over time?

• Broader context and experience: If you change jobs often (even a few times in your career) you will encounter more organizational structures, business models, leadership styles, technology foundations, cultures, software engineering methodologies, business challenges, and work styles that will give you context and perspective that you can bring to job n+1. For example, if you work at Meta or Google you likely come away with unique experience in scaling systems that almost nobody else has, and you have a network of similar people that are assets in your future. This may create a slew of future opportunities to help companies on the brink of internet scale to succeed. Perhaps you come to love this work and move around to the next “growth challenge”. This may also benefit you if you aspire to start a company since you will get a survey of more real-world problems across business domains.

• Exposure to a larger, more diverse group of co-workers: Building a diverse set of relationships with people from all different kinds of companies is one of the most important things anyone can do in their career. Networking is not just about personal benefit, but also making new friends and real connections with other humans doing similar things in the world. It can be a lot of fun. In addition, it may create opportunities for future jobs, new startups, or investment partnerships. It may help you hire the person you need for your own company in the future. When you encounter problem X, you have the “I know a person who ______” card to play.

• Comp hopping: A lot of people seem to change jobs regularly to take pay increases with each job. They often appear to be (and likely are) “moving up” faster than some of their peers that remain in one place for a long time. Risk vs. reward.

• Leadership readiness: Leadership, by nature, requires taking people to somewhere they have not been before. A diverse set of experiences may prepare some people to be better organizational leaders. On the flip side, a lot of companies promote into these roles from within.

• Developing comfort with risk: Changing jobs is risky. You may dislike the role. You may dislike the company culture. You may get laid off. Your role may be smaller than expected. It may ask you to work 75 hours a week when that is not what you expected. Getting comfortable with taking on appropriate risks is a good characteristic to develop, and this is one way to do it.

• Remain open to new opportunities: If a new opportunity comes along and you are partial to moving around, you can take it without much internal dialogue over the risk / rewards. If it doesn’t pan out, you can move again. If you want to attempt to do a startup but it fails, you move again.

• Expose yourself to new challenges: Each new role likely brings a new set of challenges in a next context, which is great experience and very engaging as well.

Benefits of staying put

What are some of the advantages of staying in one place so long? These observations are personal and are based on my own experience working at Chick-fil-A for 19 years.

• Build depth of perspective: I have been able to experience a large business (>1B when I arrived) grow into a VERY large business. During that time, I have been able to observe strategies to preserve and build culture, changes in leadership and operating structure, consistency of core values and purpose (amazing to see), historical business events (Great Recession, COVID, 2021-23 Inflation Crisis), efforts to scale and solve business challenges and evolutions of supporting technologies all in the context of the same organization. This gives me a great depth of perspective.

• Invest yourself in a purpose: Job hopping likely means not buying into a companies long-term purpose. You may agree with the companies purpose, but a quick stint doesn’t allow you to invest yourself (your time, best thinking, and energy). At Chick-fil-A, we have had the same corporate purpose in place since I was born and the efforts to uphold that purpose are as strong today as ever. By having stayed for a long time, I can see how real this is and be a small part of our purpose, which is “to glorify God by being a faithful steward of all we have been entrusted with and to have a positive influence on all who come in contact with Chick-fil-A”. I get to be a missionary (for positive influence) instead of a mercenary.

• Drive meaningful change: In enterprises, significant change generally takes years to achieve. Consider something like transforming to a “cloud first” way of building systems, which took us 3-4 years at Chick-fil-A. Being part of the entire process creates great context. By staying, you have the opportunity to invest yourself in building something lasting and committing yourself to it and its success.

• Invest in long-term relationships: It takes time to build trust, and its the foundation I try to build on top of in all of my interactions and in all my work. If you hop often, you likely spend a lot of time establishing trust but not getting to work on the platform it creates for as long. You likely have friends and co-workers you connect with along the way, but there is some unique value in working with the same people for 10, 15, 20 years. Long-term relationships enable some incredible and candid work and life conversations to occur that aren’t always possible in a shorter-term relationship.

• Rise to leadership instead of being hired as leadership: The journey teaches you humility and patience. Not to say that can’t be achieved by hopping, but there is value in rising slowly through the ranks over years of building context, skills, and relationships.

• Learn to push through challenges: It would be very easy to hit challenges, decisions you dislike, or organizational politics and just leave the company. However, I think there are life lessons to be learned in pushing through these types of challenges, learning to assert unpopular opinions (without leaving too big of a wake), learning to accept what you perceive as “bad decisions” and still commit to their success. They teach tenacity, patience, and commitment. These are critical things to know to lead effectively, whether you ultimately stay or go… but more importantly they are critical to being a person on the planet.

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Final thoughts

Does stage of career matter? If I was 25, I think I would be inclined to change jobs a little more frequently to get the benefits above and then park myself long-term to get the benefits of longevity. For me, I landed at one of the best companies in the world right out of college, and I have not been willing to leave the benefits to explore elsewhere. That’s not to say I never considered leaving: I did. But I am glad that I have stayed.

There is no right way. I believe you can compensate for the weakness of either path in a number of different ways. For example, you can mitigate the “single company of co-workers” problem by being an active networker and participant in the tech community (attend or present at conferences, go to meetups, etc). You can mitigate some of the downsides of not seeing many organizations through (more networking, yes) changing roles inside your organization so that you experience more leadership styles. Perhaps consider changing departments or functions as well.

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The Chamber of Job Hopping Secrets is closed. Thanks for reading. If you found this useful, please share with a friend or co-worker. Have a great week! 🙏