1792 Alysheba Way, Suite 201, Lexington, KY 40509
FINRA | Broker Check | SIPC

How Long Will You Keep Working?

There’s a question I’m frequently asked by clients who are reaching a certain age, and I’m hearing it now especially from folks who aren’t sure about heading back into an office post-pandemic: How much longer should I work? Many folks are thinking differently about their daily working life after a year of working from home, or perhaps having to change jobs into something less fulfilling. 

Of course, there’s no simple answer, and there’s no one-size-fits-all solution. It comes down to dollars and sense (see what I did there?). If you’re unhappy or disengaged in your job, it’s an easy decision to make. There are a few of you who truly don’t enjoy working, and for the folks in this group, the discussion simply comes down to dollars. We’ll take a look at what you’ve saved, your pension (if eligible) and Social Security benefits, who will pay for your medical costs (you or former employers) and if you’re 65, it’s time to talk about Medicare. We’ll also look at current lifestyle, future goals, and what you plan to do in retirement – whether that’s more or less than your current lifestyle. 

While dollars will allow you to answer the question, “will this work, financially?”, the sense part is the trickier side of the equation. Many people do enjoy their jobs, their coworkers (most of them, anyway!), and find happiness in the structure that comes with working every day. For the people in this situation who are blessed with solid finances, you can work as long as your lifestyle is within your budget. The sense part causes some conflict as these folks near traditional retirement age, and this is when clients start talking to me in hushed tones: “But Dave, does it make sense for me retire?” 

In reality, this is not a financial question. Folks in this situation aren’t sure they’re ready for that kind of lifestyle. They’re wondering who they’ll hang out with from 9 to 5, and many are scared of missing out while the world continues on. I used to think clients would tell me that finances were their real concern. But when people ask me this solemn question – does it make sense – I’m starting to understand that for many of you, retirement is a scary word. Working is so much of who we are. It allows us to be us, to be active in our work communities and mentor younger people. Working makes many people feel appreciated, and that’s created by the fact they are showing up and engaging in the workforce every day. 

The folks in this group, the ones who do love their jobs and careers, face a real conundrum. They like the relationships and friends that their jobs have created over the years. To think of not doing that, of being home alone while the kids or grandkids are at school, well, it’s something many choose not to think of. 

So, when will you know how long you need to work? It would be great if I could tell you there’s a simple mathematical answer. We’d all get warm fuzzies if I could assure you you’ll be happy once you quit working, but I can’t, and I won’t. 

The truth is, you’ll know when it’s right because you’ll start to embrace the idea instead of speaking about retiring in hushed tones, and you’ll start to dream about all the possibilities that await you. Retirement shouldn’t necessarily be based on age, and it shouldn’t be forced. Your personal retirement plan will happen when you’re ready, whether you’re 50, 90, or somewhere in between. 

As for getting to the point, financially, where you can make that choice? We can help you do that, and the sooner we start the conversation, the better. Let’s talk timing next time we meet. 

Scroll to top