I was at the local grocery store when I ran into an old colleague who lived in town. We exchanged pleasantries and chit-chatted about my new position teaching for the last year. I told him how much I enjoyed the job and how it was challenging in a good way.  It was a great new mountain for me to climb from a career perspective.  Then they asked me “Did you hear about (your old boss)?”  They then proceeded to tell me that my former supervisor, after many years, had abruptly left the position they were in.  This was a huge shock, as my former supervisor was a rock of stability.  They were never the type of person who would leave a position abruptly so this type of action was completely out of character.  In truth I didn’t believe it at first.    I naturally made some calls over the next few days to confirm the news and figure out what was going on.  As I started to pay more attention to the situation I came to the conclusion that why they left wasn’t nearly as interesting as what happened over the following few weeks.

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An important point about my former job, at least important for this narrative, was that we were a very stable and close-knit team. We had our ups and downs, but for the most part the majority of the team was rock solid and most of the members were long-serving.  Within weeks after the departure of our boss, other very long tenured former colleagues left the organization.  In effect the team completely dissolved.  It’s not like they did the corporate thing where a team leader would find a better professional home with greater opportunities and then recruit their old team to work at the new company.  Most of my former group just left.  They simply didn’t want to be there anymore.  I looked around and I realized  I was pretty much the last man standing from my old team.  What I mean is that even though I wasn’t working in that area of our organization, I was still employed with it. 

This isn’t the first time this happened to me. In fact it’s happened more than a few times before.  The next  most recent similar experience was the job right before my current one.  It was  when I worked for an ISV who tried to ramp up several sales teams for a huge new product launch.  I was brought on board with a dozen or so other sales reps with promises of guaranteed success and job satisfaction if we worked hard.  As I’ve told the story often, the organization turned out to be a boiler room sales operation with a vaporware product, and a criminal for a CEO who was ultimately convicted of embezzlement of tens of millions of dollars.  It was miserable, and within weeks, everybody they hired was looking for a new job. Fast forward a year and a half later, and I was the only one left.  They eventually let me go too but for a few months there, I was being shuffled around from team to team. This was because there was nobody left from my original team, which was dissolved, and I was being used to plug holes in the other teams as people escaped the company.

I’ve heard these stories from other colleagues over the years.  When a pivotal member of the team leaves, usually the leader, the team disintegrates.  There are many reasons for this, but they aren’t the point of this article.  The question that’s rolling around in my head,  is why don’t people just stick it out?   I know my old team and they could have easily stayed on board if they wanted to.  Yes, there would be new leadership, and there would be a transition period, but it was a very good group that could have weathered the storm.  Ultimately I wondered what are the pros and cons of sticking with your job even when everyone around you is jumping ship?  I came up with a few.  


The first and most obvious benefit to sticking with your job is your income. Remember, I was close with my former colleagues.   One of them left without another job waiting for them.  Financially their household could survive on a single salary.  Their plan was to wait it out about six months and then get back looking for a job.   I can appreciate the desire to take some time and focus on other life  goals. At the same time, when you include salary and benefits, you’ve got to be looking at between a thirty to fifty grand impact to the household.  And that’s assuming they get another job right after that six month window.  That is a hard number for me to swallow.  

Another benefit is understanding the lay of the land, professionally speaking, and all of the value that brings.  By knowing the idiosyncratic details of the organization, it can potentially allow you to be much more efficient at your job.  As an example, if you need a sign off from some remote organizational VIP to get one of your issues resolved, you may spin your wheels at a new organization trying to figure out how to get in touch with them.  Because you’ve already gone through that process at your existing organization, you may know which one of their lieutenants to approach when the VIP doesn’t return any of your daily emails you’ve been sending for a month.  These little shortcuts take years to learn and they’re almost impossible to transfer to a new job because they are so tied to the existing organization.

This organizational competence is especially valuable if whoever comes in as the new boss is from outside the organization.  All of a sudden you become a key team member when you can help the new person navigate all of the little questions, issues and challenging dynamics that anyone will run into when they come into a new organization.  This benefit doesn’t go away in a few months.  I once read some statistics about how long it takes to really get to know a larger company. It turns out it takes years to understand all of the intricacies of a large organization. This means the new boss will be relying on your knowledge, at least a little, for years.  If you manage it right, this can lead to a more secure job than you had before the upheaval.

Another benefit of sticking around is being able to take advantage of new opportunities.  It could even be an opportunity for a big promotion. Sometimes organizations don’t pull from the outside and when everybody else is gone, you’re the obvious choice for the top spot.  I think there are other opportunities which can be leveraged. For example, if there’s a little project you’ve wanted to take on  or a new way of doing things you’ve wanted to try, and the old boss didn’t like those ideas, maybe the new one will. Realistically, there’s a good chance of pulling something like this off. No matter the situation, the new boss almost always wants to do things at least a little differently than the old boss.

Even if the new environment is a total shite show compared to how it was under the old boss, it may be worth sticking around for the financial runway. You’ll have an income and as I’ve mentioned earlier, income means you don’t have to make drastic changes to your lifestyle outside of the work hours.  Also, it’s always better to move from being employed at one job to being employed at another. For whatever reason, recruiters are prejudiced in favor of those who are already employed.

Of course sticking around after everyone else has left the building is not a panacea for the issues you run into at your job. There are definitely cons for finding yourself in the position of ‘last man or woman standing’.  


Depending on the situation that the old boss left the organization with, the new boss may have been given an edict to clean house.  They may keep you around for a little bit as they get settled and learn all they can from you, but your days could be limited and you wouldn’t know it.  I find this nefarious, but it’s standard practice across many business group transitions.  As I’ve mentioned in the past I think the best case scenario is transparency on the part of the organization as to your longer term prospects at the company as well as a truly useful severance program of at least six months full salary and benefits, and then two months for every year employed.   Of course this shifts the risk to the company, something they have been actively working against for decades now.  If they tell you in advance, you may choose to lower your quality of work or leave as soon as you can make an exit that’s in your own best interest.  

There is also the possibility that there is a stigma attached to the old team.  I have to admit I personally haven’t experienced this too much in my career, at least not that I know of, but it’s there.   I know it is because I’ve heard the predjecual comments.  “Oh, they used to be from XYZ group” can be said with a derogatory tone that can influence others.  It is true that over time a groups culture can sink into the individual.  I’m much more risk averse today professionally, in part, because I adopted the risk averse culture of the team that I used to work with.  

There is an opportunity cost as well.  Depending on the macro employment environment in your industry, part of the exodus could be because things are better at other competitive organizations.  Loyalty and comfort can be a big impediment to career growth opportunities that require changing where you call your professional home. 

I’ve talked about the Pro’s and Con’s of sticking with the new job, but thinking about it from the other angle, you have to ask about the pro’s and con’s of jumping ship.   Looking at the mirror image of being the last man standing, if you jump to another employer, then there are some benefits and maybe some cons too..  

Benefits of Jumping

I think the first benefit of jumping to a new organization is the honeymoon period.  It usually lasts about three to six months or so, but in some cases it can be much longer.   I’ve found that when you get to a new company you can make some quick impact via ‘low hanging fruit’.   Also, everyone is much more flexible and accepting with mistakes.  How could you know, you are new?  It doesn’t last forever, but the honeymoon period is very nice.   

Another major benefit is greater upward mobility.  This is assuming you will shoot higher when you next jump.  Clearly it’s best to do this when you are planning to move from one employment situation to another.  It just doesn’t work as well when moving from unemployed status to employed.  As much as I hate to admit it, there is probably some small truth to the prejudice maintained by hiring managers wanting people who are currently employed.  Nobody can see a layoff when the change is in the ‘act of god’ category.  I’m looking at you Covid Pandemic.  I do think there is some truth to the idea that people who are proactive are a bit more insulated at the company.  I remember years before my wife’s company was sold, the company made a strategic shift in the customers they were targeting.  I told her at that time it was the owner and C-suite team planning their exit strategy.  I believe I was right.  At that time she could have done a few different things to prepare for the buyout and protect herself with the associated mass layoffs.  Still that would have been a ton of work for nothing other than an educated guess.  

Another benefit to making the jump when you are the last man standing is that it’s an easy explanation in the interview to the question of “why are you wanting to make this change?”.  This is a question that’s always asked if you have any sort of tenure at your existing company.   When there is huge change and upheaval at work, then it’s reasonable to look for a new job.  The recruiting team will understand this and no alarm bells will go off for them.  This could also work in your favor if you are saying you are looking for a more stable and long term position, something HR recruiters always want to hear out of a prospective candidate.  

We can’t forget the emotional component.  Let’s be honest, a new job is like a new relationship, it’s always exciting at the beginning as you learn about each other.  Every day is something new.  Some will be negatives, some will be positives.  

Negatives of Jumping

In thinking about it, the biggest, and probably only negative in choosing to jump with everyone else  is that you don’t know what you are really getting into.   Nobody proactively moves to a worse situation.  To make a move into a new job, the benefits need to outweigh the current negatives.   That being said, the recruiting process could have been all smoke and mirrors.  It could be like the situation I got myself into where the new company is a burn and churn organization with little regard for people.  Thankfully, this is a different era.  With sites like Glass Door among others, it’s easy to see what it’s like working for a company.  In addition to these sites, some good old fashioned networking will allow you to get your homework done on any potential employer so you can, mostly, avoid the bad ones.  

Going back to considering my last man standing situation, I get why I’ve been in that situation a few times.  I prefer to stay rather than make a move. I like stability in my life so that has a tendency to win out over other considerations. Sticking around is usually more stable.  The decision to move on is a difficult thing for me but maybe not for others.  Still, when there is upheaval and you look around and realize your the last person it’s a sign to really consider your options.    Unfortunately, there is no clear answer.  Even with my perspective of leaning towards what I consider the more stable option,  I can see that it really is a crapshoot.    You can stay or you can go, and honestly, when change is in the air, typically there is no right choice, so you have to do what you are most comfortable with.  Maybe I’m wrong about that.  There is a correct choice.  I say that because your choice, the one you are most comfortable with, is absolutely the right choice in any situation where you look around and realize that you are the last man, or woman, standing.

Posted by Mike Peluso

Mike Peluso writes about the collision between between the business / professional world and life. He also writes about the journey involved with the Peluso Presents efforts including the Blog, Books, and Podcast so that others may benefit from his efforts. From Mike: I spend hundreds of hours working on these articles every year with no compensation other than support I get through donations. You can support with a tip and by Subscribing to the Podcast (and writing a review on iTunes would be really appreciated as well!) One time tips: www.paypal.me/pelusopresents https://venmo.com/pelusopresents

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