Doing these five things is going to help you get set up the right way for your future retirement. So if you’re thinking that you might be five years out, or even if you might be a little bit closer, this post will be helpful for you. 

First, don’t think about the numbers just yet. 

Start out by thinking about your reason why behind wanting to retire. This is critical because while we’ve seen a lot of people who feel fulfilled in retirement, we also see people who feel bored or lost in retirement. Finding your motivation and your why behind retiring is a very key part to enjoying this next stage of life. Here’s a good question to ask yourself: what would I be able to do in retirement that I can’t do now?

And as a side note, we’ve heard from quite a few people who retire and then wonder a few months in: is this it? What am I supposed to be doing all day? And it’s quite an adjustment. It takes a while to get back to a point where they feel like they’re moving in the right direction. So, think about that question or click here to request a guide on How To Find Your Purpose In Retirement

One other thought related to this point is: rather than thinking that you have to go cold turkey, from working 40 or 50 hours to zero, think about what-semi retirement can look like. Consider going to half-time, or maybe a different position in a different place that would be less stressful. That could be a great way to transition into this new stage of life. 

Second, take a guess at what your monthly expenses are going to be in retirement. 

What are your monthly expenses going to be in retirement? How much would you need to have coming in to cover those expenses? And then, look at your current expenses, or think about whether expenses are going to go up or down for you in retirement and start to think about those numbers. There are some helpful tools out there that can help automatically track your expenses now and categorize them for you. For example, is a free app that helps categorize things so you can look at expenses more closely.

Third, look at, and research, your healthcare options. 

Here are a couple of things to look into: 

  • Check with HR to see if there any options for after you leave work. 
  • Look at your spouse’s plan and their options. Are you going to hop on your spouse’s plan for a few years before 65? Check and see how much it would cost. 
  • If you’re under 65, what would health insurance cost before you get to that Medicare age?

Fourth, get organized on your future income sources and assets. 

Log on to, to check your Social Security and write it down. Also write down any pension income. Look at your 401ks, IRAs, and other accounts that you may draw from in retirement. And then with those pre-tax accounts, think about what age you can begin withdrawing without a penalty. You may have to wait until age 59 and a half, and there are some 401ks that allow you to take money out at 55 and not pay a penalty. 

Then also look at how when you start collecting Social Security, it can impact how much you get each month. Click here to see a video on working while also taking social security. 

Then run at least three retirement calculators. I created the “How Much Do I Need To Retire?” quiz, which you can access by clicking here. Another retirement calculator that I like is from Nerd Wallet. You can also just Google retirement calculator and see what comes up. 

Finally, start tracking your net worth.

Tracking your net worth is so important because once you figure out the income and the assets that you’ll need in retirement, then the net worth number can be a great way, and one of the easiest ways, to make sure that you’re on track to get to those goals that you had written down. Again, is one way that you can track net worth. Here at Streamline, we actually create a private dashboard for our clients that has your entire financial life in one place and tracks your net worth as well. Whatever you use, tracking net worth is going to be a helpful exercise as you get closer to retirement. 

If you have questions about retirement planning, investing, income planning, or even taxes around retirement, please reach out to me for a phone call. I’d be happy to have a call with you if there’s time available.