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Strategies for Staying at the Same Company Long Term

On Being a Lifer

If you look at my bio, you might notice I have been at SentryOne for 9 years. That is a mini lifetime in tech. I like to joke that I am the longest serving, lowest ranking person at the company. (Shhh, that’s part of the secret. 😉)

I thought it would be interesting to discuss some practical strategies and coping mechanisms for surviving, and hopefully thriving, in long-term employment at the same company. I also thought it would be good to talk transparently about both the good and the not so good that comes with working for the same company for many years.

Push Yourself Beyond Your Comfort Zone

When you have been with a company for a long while, it can be hard to disassociate what you actually know from what you actually do for said company. At some point, as you become a lifer, you have bought in. But just because you have bought in does not mean that you should be comfortable.

In fact, if you look around at the lifers at your company and they are all coasting, having achieved some imaginary potential ceiling, I doubt there is much future success ahead for anyone. If you look around at your lifers and find that they have changed roles frequently, solving the next set of problems as the company has evolved and scaled, that is a good sign.

Be restless! Not everyone wants to or will be able to quench that need in the same place, so growing out of a company is certainly a possibility.

As a lifer, there is a potential risk that your skills might not keep up with the outside industry, and there is risk that you can become too comfortable. The secret here is the type of company you attach yourself to. I’ve been fortunate, as I view SentryOne as the type of company that continues to reinvent itself and adopts new technology at a significant pace. With that way of thinking being a part of our company culture, getting comfortable is not the natural path.

Strategies for Surviving and Thriving

This is my second long-term job in adulthood, having done a previous six-year stint in the United States Air Force. Obviously, that commitment was a bit different given that once you sign up, the Uniform Code of Military Justice (UCMJ) mostly mandates that you honor the commitment or, you know, they send you to jail. That being said, the Air Force did give me my first exposure to the rewards and benefits that come with loyalty.

When I say loyalty, I am not necessarily talking about my loyalty to any company entity. You see, the Air Force taught me about loyalty to the people I work with, to the woman or man next to me that is helping me accomplish the mission, cope with the day-to-day, and get things done safely and rationally.

Find a Company Where You Genuinely Care About the People and Culture

Although the mission and the Air Force transitively benefited from our joint commitment, I found out through that experience that it is the commitment to my colleagues that actually matters to me. My advice is to form an emotional attachment to the people you work with, not the brand. That is what humans authentically do, and it works.

So, my first strategy for sticking it out long term is to find a place that cares about hiring quality human beings you want to spend your time with and preserving and protecting a culture that people want to live in. Ever take the Gallup Engagement Survey? There is a question about having a best friend at work for a reason.

Focus on the Things You Can Influence

My next strategy for staying power is to avoid the negative and focus on your area of influence. I previously wrote about area of influence versus area of concern in a blog post about building a DevOps culture, so I don’t want to get too far into the concept. The short version is to be a constant problem solver.

People don’t mind problem identifiers, but problem solvers are really appreciated. It is not always going to go right for you, so you need to be able to roll with failure and get back up. I have read advice that says not to say the phrase “I’m sorry” when you make a mistake in a business context. I do not completely buy into that. I think apologizing for a mistake under the right circumstances is fine. However, I do think it is more important that you share a plan for ensuring that particular mistake does not happen again. For a business, a plan to solve the problem is always superior to an apology.

Give the Benefit of the Doubt

This strategy is similar to the previous one but is more focused on how you perceive others and discuss mistakes, I see it as beneficial to both your mental health and staying power. Avoid assigning blame when there could be a simpler explanation. Someone pointed out to me that this is similar to Hanlon’s razor, with a friendlier spin.  If you are familiar with a blameless postmortem, it’s not unlike approaching every interaction just like that.

Even in a mid-level role, you are going to participate in the process of making thousands of decisions a year. At the individual contributor level, you will be downstream from even more decisions. Give the people who work for and with you, and the people you work for, a reasonable benefit of doubt.

Mistakes are not character flaws. Don’t trump them up to be or gossip about them. It’s valuable to have language available to deescalate exchanges that tend toward character indictments. For example, instead of a person being an idiot, pivot the conversation to the information that led to that decision. What can look like an obviously bad decision on the surface is often a culmination of bad information and unrealistic timetables.

Acknowledging the Bad

No matter the strategies you might acquire in your career path, I would imagine most of us still have to deal with several of the less than ideal aspects of long-term employment. Let’s look at a few of those aspects.

Living with the Entire Past

If you are married or in a long-term relationship, you know how your significant other remembers several great things about you, but absolutely doesn’t forget any bad things. I am sure my spouse could make a list. They have seen your triumphs, but they also have helped you crawl out of some tough spots.

Being at a company for a long time, and watching it grow and figure itself out, is not unlike navigating a long-term relationship that has had a few ugly spots. Some of those spots you contributed to yourself and some of them you wish you could forget, but if you are going to make it through, you have to acknowledge them as real and try to do better next time.  

The recent economic downturn comes to mind for me, and I am not talking purely about economics. Obviously, that part is affecting entire industries. The real human impact has been painful. Having to furlough or let go of someone you care for and perhaps mentored, or see someone leave who has mentored you, carves a permanent scar in you. There is not a “good” way to have those conversations. There are arguably strategies to do it as compassionately as possible, with care, transparency, and kindness. But given the nature of the news, the conversation is not likely to end in any immediately positive place.

I will not wax on about my experience on this much further; it’s not really fair or reasonable. It is better to seek out and listen to those impacted and think about how we can be better. It does not matter if you think you did the best you could. It happened to them more than it happened to us. From a human-to-human perspective, we owe them the time.

Your Job Debt

I am sure there is a better name for this phenomenon, but a lifer’s job debt is not unlike technical debt in any given software project. The debt builds up over time as you make decisions to satisfy short-term needs, at the sacrifice of long-term maintainability. In the case of a lifer’s job debt, the thing you need to maintain is your emotional health. We don’t talk about emotional and mental health enough in tech or in our society. Changing jobs can certainly be a way to experience an emotional reset.

A benefit of leaving to work for a different organization every couple of years is that you no longer have to deal with that special thing you built a couple of years ago in order to meet a specific deadline. Sticking it out somewhere long term means you can’t ever really let go of what you have done. That grand idea you had 5 years ago when you had some downtime? Yep, you are still on the hook for it. That person you recommended that ended up not really working out? Everyone remembers. That thing you built in 2012? Well we need it to interface with Salesforce, and can we maybe run it serverless or maybe you can make it cloud agnostic just in case we change providers in the future?

I did it to someone myself recently, I reached out to them about something they owned ten years ago because, well, I needed an answer and I knew they would help. They graciously answered but it took time, and I doubt anyone really recognizes that person still spends cognitive load in that area. Over time, that load you are maintaining can slow down your creativity and your ability to innovate.

Acknowledging the Good

Let’s end on the good, because there is a bunch of good in my opinion.

It’s About the Relationships

As I touched on in the Strategies for Surviving and Thriving section, the best part about being with a company long term are the relationships that you get to build with your colleagues. When well maintained, those relationships are likely to develop mutual trust. Once you have enough of those trusted links, you are likely operating in that sweet spot of empowered autonomy. You are then solving problems with and for people, with the correct amount of involvement from other parties, and playing to each other’s strengths. Productivity aside, I can honestly say that there are dozens of people at work that I completely trust. These people can read my mood, I can confide in them, and I absolutely care for them. It is hard to quantify that benefit.

I talked about the long-term relationships I have built with other lifers here at SentryOne, but I want to acknowledge the good that comes from the relationships you get to build with newcomers. One of my favorite aspects of having been here a long time are all the people I have gotten to know within the SentryOne world. Not all of them have stuck around, but I tried to build a relationship with each one just the same. As a lifer, you need to pay special attention to those new employees. Odds are they know a few things that could benefit you, they might have solved some of the problems you need to tackle, and no matter their experience level they bring a different perspective. Teach them about your sacred cows and let them show you why you are wrong. Use your position to help amplify their good ideas. Offer in trade historical context about how you got there. In short, learn everything you can from them.

Be T-Shaped

Another great benefit of sticking it out long term is that you can more easily try on several different hats. There is always a ramp up time at any place. I’ve seen people who are brilliant at grokking new places hit the ground running and be a top contributor within the month, but I’ve more commonly seen people need closer to six months or even a year to ramp up.

Switching roles within the same company can accelerate that ramp up time, or even get rid of it all together. Having gotten a chance to spend time doing support, documentation, quality, and several DevOps-focused roles during my time at SentryOne, I see this capability as a big positive.

Use Your Voice

The last benefit is something that has crystallized more for me recently. I could sum it up as accepting that some level of capitalism exists in society, that you are part of it, and that being at a company a long time gives you a better chance to help ensure that it is done responsibly and equitably. Longevity gives you the chance to be heard, but more importantly it gives you the chance to shut up and amplify those around you that should be heard.

Just to be clear, this crystallization was not driven by my own actions. Instead, I have reached the conclusion over the past couple of months while watching several long-term employees step up to lead discussions and help us steer through both our company’s response to COVID-19 and the subject of racial justice and equality within the United States. I see you all and I thank you for helping SentryOne be better.


It was a rewarding experience putting these thoughts together, and I hope you got something out of this blog post on being a lifer (aka, a long-term employee with the same company). I covered some strategies for how to survive— and hopefully thrive—during a long stint working for the same company. Then, in an effort to keep it real, I also talked through some of the bad that comes with long-term employment. Finally, we dug into what I see as the benefits, which I ultimately see as making it all worth it.

If you have any additional ideas to add to the discussion, join the conversation on LinkedIn or Twitter. As always, I’m happy to connect—just reach out.

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Eric Smith
Eric Smith is the DevOps Engineering Manager at SentryOne. Eric's team focuses on optimizing the process and tooling used by our delivery teams and evangelizes…
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