It’s something that many future retirees may encounter when within a couple of years of freedom. The closing in on retirement dilemma of whether to stay put in the job or move on to what might be a better opportunity. Something that may even shorten the remaining retirement time frame if the earnings are better. I had this quandary when I was a year or so away from my targeted retirement goals. In my case the decision was made for me. Just in time before I might have regretted what I was about to do.

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The Common Closing In On Retirement Dilemma – Move On or Ride It Out

We’ve all heard the saying, the grass is always greener on the other side. If there was ever a time to pay attention to that idiom, it’s when we’re closing in on retirement. The trick is to spend a little time examining the other side with a clean pair of glasses. We need to see if it’s really better. Sometimes we are looking through an emotionally smudged lense. In my case it was a close call and I ended up staying put until hitting my retirement target. 

During my final year I was tempted by a lucrative offer to jump ship and I was about to accept it. Luckily for me they decided that their business was going to downsize days before things were finalized and fortunately the cat was still bagged. Both the project and the offered position were cancelled. Days later word got out about all of their coming layoffs. How different my retirement timeline would have played out had I made the move and that company’s decision was made after it was too late for me to reverse course. 

It was a quick eye opener and I instead stuck it out where I was until my early retirement time. Months after I retired I started on some rewarding paid retirement job adventures. I can see how different those experiences would have been had I started them before I was retirement ready. 

Here’s how it went with me. Something to provide a few thoughts to go through before making a decision to either make or avoid a pre-retirement job move.

What’s exactly motivating the urge to jump ship when almost home?

How do we really feel about the job?

It’s easy to become impatient when getting close to our retirement date. Things at work that have always irritated us will only amplify. I had plenty of them over the decades in my first career. My “closing in on retirement dilemma” of whether to stick it out of skate off was primarily motivated by the constant post company merger executive’s insults. Insults that were both financially and policy driven against those of us who actually did their jobs. 

Since we are close to the finish, we should focus on the light at the end of the tunnel. We have to assess and ask ourselves whether we like the company, people, immediate management, work, environment, conditions, pay, etc. If the answer is yes for the majority, maybe sticking it out might be the logical decision. If not, nobody should have to stay in an intolerable situation if a better opportunity presents itself. 

The power of seeing prospects of more money

A sprinkle of impatience and a pinch of greed may be all it takes to believe we’re seeing retirement sooner than planned or going with a bigger sendoff. Who wouldn’t want that? There’s always the temptation to chase after more money. If the runway to retirement is long enough, then this is a powerful motivation and maybe a good move because pitfalls would be most likely-short-term in the entire time-frame scheme of things. If it’s a short retirement runway with a higher impact of error, maybe not so much. 

To temper my enthusiasm and emotions so that I could logically think my way through, I reminded myself that my current salary, although less than what was being dangled in a new opportunity, still provided a near retirement date. It helped, but I was still swayed by dollar signs.

Applicable Lessons Learned Comparing My First Career With My Retirement Jobs

Nothing is guaranteed

I admit I was shook when everything collapsed as it did while trying to solve my closing in on retirement dilemma. Timing of the new company’s coming reductions was in my favor. But it would have been devastating had it come a week or two later. I would have been left desperate to find another position and most likely adding delay to my retirement plans. 

As good as a new offer looks, there’s no guarantee that it will be fulfilled or last. Sure, the same goes for our existing positions. But at least with time on the job there is usually a severance benefit if let go. If in the final stretch to retirement that may be enough to get us there. We must always remember that all of it is a delicate dance. Business has its priorities, and we should have and guard our own priorities.

All the workplace annoyances

When we’re in a long-time career we can think annoyances are isolated to only where we’re working. Surely there isn’t the same propensity for shenanigans and insult as there is here? The reality is that this happens everywhere. 

How I got through the last stretch to retirement was to figure out how to better avoid the irritating people and policies. With no motivation or ambition for advancement in my soon to retire mentality, I just focused on doing the parts of my job that I did best. I then leveraged their game using their annoying new rules to my advantage while holding my nose to get to my primary goal: Leaving on my terms when I was ready.

After I retired I started some great retirement gigs. I saw the same irritating nonsense going on that I saw before, but what wasn’t the same was me. I didn’t need to be there, I wanted to be there. Having the power to walk away anytime and having zero financial threat for failing to please a company idiot changed everything. It’s easy to tolerate the side stuff when the employment power dynamic is flipped in your favor. 

Money isn’t everything

I was tempted in my final stretch to retirement by what looked like an exciting project with what was a different growing company along with a big raise. The near miss made me think hard about what might have happened. 

I tried to stay objective by reminding myself that money wasn’t my primary motivation in the overall scheme of things. Early retirement on my terms was. That’s what’s at risk if things go wrong. If money was all I cared about, I certainly wouldn’t be on track for an early retirement just down the road, I’d instead just stay working to pad my net worth. No thanks!

Even so, I still fell for money’s lure in my last stretch before retirement. My near miss experience did teach me how to better prioritize and prepare myself for my enjoyable retirement jobs that came later. I had won the game by reaching my financial goals and could truly only accept work that I had interest in doing. Best of all, without having to meet any financial obligations or goals, I only had to do it for as long as I wanted to. There’s truly a huge difference between needing to work, and wanting to work. Taking on a new opportunity while closing in retirement would certainly fall into needing to work.

I found my retirement gigs much more enjoyable and the money earned was just the cherry on top. I also realized that money wasn’t proportional to job enjoyment. My first gig was lower paying than my career. My second retirement gig paid more than my long career. Another paid way less than than all of them. I enjoyed them equally and way more than my long-time career. 

How hard are we really willing to work during our last leg of employment servitude?

When we have been in a position for a long time we may be working hard but it is known, understood, learned, and productive work. Our work and reputation has already been earned. A new position means we will most likely have to reprove ourselves. There’s the stress of learning new job duties. But also learning the new company culture, processes, determining people to align with and those to avoid, etc. All with the pressure to succeed because we still have retirement date goals that are within reach if we pull it off.

Some may find it appealing to just coast on their long-time job through their final stretch to retirement. That wasn’t me, although I often wished it was. There probably wouldn’t have been any closing in on retirement dilemma to work through. While in my long-time career I was ambitious, taking on new responsibilities, and attempting to increase my knowledge and skills. What I found later during my retirement gigs is it was a lot easier to do in a company and position I had been in for years. 

Once I entered into new retirement opportunities within similar technical fields, I experienced just how challenging and stressful it is to feel that I was performing sufficiently. That feeling of inadequacy would have been excruciating if done worrying about survival to make my retirement date goal. In my post-retirement experience that specific new job pressure wasn’t an issue. I just needed to satisfy my own feelings of adequacy. It takes a while to retrain our brain to overcome all of the stress that can come with a new job. I will say that all got easier to menatlly get through with each new paid retirement opportunity I took on.

Risk is always there

In some cases it doesn’t matter how well we perform or how solid our plan is. There’s always the risk of outside forces overturning everything we have worked towards. Just as in my close call when business and economic conditions abruptly changed. It can happen whether we stay put or chase a new opportunity.

That near miss and my retirement work experience showed me that the biggest hedge against expendability by these outside forces is reaching our personal finance goals. Something to focus on when experiencing a closing in on retirement dilemma of whether a late career move is the way to go. If the odds look great to make a move or the risk reward is worth it then do it. If not or not sure, then stick it out until the odds are more in your favor or when you can freely chase opportunities post FIRE.

It will always be a tough dilemma

I know that I underestimated how competitive and ruthless the working world can be. After dealing with and managing levels of it in my long-time career, I failed to think it could be even tougher starting somewhere new. I wasn’t a starry eyed fool. It’s more about being lulled into complacency after decades at the same company and then receiving a good opportunity pitch. 

Everyone will have to decide for themselves whether to stay put or chase a new opportunity in the final stretch to retirement. Sometimes the stars will align and an opportunity is too good to pass up. For others the prudent move might be avoiding any rocking of the boat that got them there. Regardless of how impatient and annoyed we are during the last stretch along the lines of the saying, better the devil you know.