What do you want for your retirement? If you’re in the latter part of your career, it’s time to start thinking about that question.

Halsey Schreier

April 17, 2023

Creating your ideal retirement lifestyle starts by working with a trusted financial partner, no matter where you are in your journey to retirement.

The latter part of your career — in your 40s, 50s and early 60s — is the prime time to position yourself for a successful retirement. While your “post-work” years may still seem a long way off, the time will pass quickly. For some, retirement may come sooner than expected as layoffs, illness or the responsibility of caring for another may cause you to leave the workforce earlier.

As a result, it’s important to start your retirement planning as early as possible. We previously discussed the planning steps for your 20s and 30s, including five actions you can take in your early career to set up “future you” for retirement success. Now let’s look at some things to consider as retirement draws closer and becomes a more tangible reality.

Steps to take as you get closer to retirement

#1. Visualize your ideal retirement.
Many people have a vague idea of what they want from their later years but no specific plans. People are far more likely to be able to enjoy their retirement years if they take the time to visualize and plan for it earlier in their working years. Sure, planning for the future is no guarantee that will go as you envisioned. However, answering a few questions can provide clarity and serve as a jumping-off point for the planning process.

Here are a few questions to ask yourself as you’re thinking about your ideal retirement:

  • When do I want to retire?
  • Where do I/we want to live?
  • Will I continue working in some capacity? If so, do I want to work fewer hours or in a different capacity?
  • How do I want to spend my time in retirement and with whom?

Keep in mind that your answers to these questions may shift over time, particularly as you get older and your life circumstances change. We recommend asking yourself these questions every few years, writing down your answers each time so you can see how they evolve through the years.

#2. Create a financial plan to match your goals.
Once you have a clear picture of what you want retirement to look like, you can begin to determine how much cash flow you’ll need to make it happen. This starts with a thorough assessment of the amount necessary to cover your fixed and variable expenses in retirement. These will likely include costs such as:

  • Housing, including mortgage or rental payments, insurance and repairs
  • Transportation
  • Food
  • Clothing
  • Taxes
  • Medical and insurance premiums
  • Travel
  • Hobbies
  • Gifts

It’s not easy to anticipate how much you’ll spend in the future, especially if retirement is still 20 years off. However, you can use your current spending as a guide. Don’t forget to think about which expense categories might increase or decrease in your retirement years. For example, your housing expenses might decrease, especially if you downsize or pay off a mortgage. However, your medical costs will likely go up as you age.

#3. Evaluate your current assets and future income.
Now that you know how much money you’ll need to cover expenses in retirement, it’s time to assess potential gaps between those expenses and expected cash flow from your asset base. When planning with a client, we generally ask three questions as part of the evaluation process:

  1. How much cash flow will you need in your 60s, 70s and beyond to support your desired lifestyle?
  2. Are your projected assets sufficient to provide the necessary cash flow?
  3. What steps could you take to address current or future gaps?

Gaps in your retirement plan occur for several reasons. Sometimes, they’re due to shifting market conditions, resulting in an underperforming portfolio. Or maybe you put a plan in place years ago, and it hasn’t been updated to reflect significant life changes. No matter why the gaps exist, there are usually some options for rectifying them.

First, you may need to reallocate assets to realign with your risk tolerance and timeline. We often see this happen with clients who have been saving and investing for a long time, but haven’t adjusted their strategy as they’ve grown older. A second method to address gaps is to consider redistributing income into different “buckets,” utilizing a mix of tax-free and tax-deferred accounts. One example would be converting tax-deferred accounts (such as a traditional 401(k) or IRA) to a Roth IRA. By paying the taxes on the conversion now, you won’t pay taxes on distributions from a Roth account during retirement, but may have a greater tax burden during your working years. You want to discuss any potential Roth conversions with your financial and tax advisors

#4. Organize your financial life.
Other actionable items you can do as you draw closer to retirement include maxing out plan contributions as much as possible. If you’re age 50 or older, you can take advantage of higher “catch-up” contribution limits for employer-sponsored plans, IRAs and Roth IRAs. Now is also a good time to work on reducing or eliminating large monthly expenses, such as mortgage payments or credit card debt.

Your insurance needs likely will also change during this time. If your children have reached adulthood, you may no longer require life insurance and may be able to eliminate premium payments. However, your 40s and 50s are an ideal time to evaluate your potential need for long-term care insurance because premiums are typically lower when you buy a policy at a younger age and while you’re still healthy.

Evolving family dynamics may mean it’s time to update important legal documents, especially if you no longer have minor children or recently added new branches to your family tree. If you haven’t already, your 40s and 50s are ideal for establishing trusts, wills and powers of attorney. It’s best practice to review these documents on a regular basis, ensuring beneficiaries are up-to-date and your assets will be distributed according to your wishes.

Finally, we recommend establishing a relationship with a financial advisor if you haven’t done so already. You’ll be required to make many decisions as you journey through the second half of your career, and a financial advisor can help you understand the pros and cons as you weigh each decision and navigate the path to retirement.

Creating your ideal retirement lifestyle starts by working with a trusted financial partner, no matter where you are in your journey to retirement. From investing and saving to future cash flow and legacy planning, CIBC Private Wealth works with retirement savers of all ages and backgrounds. Visit our Private Wealth page to learn more.


Halsey Schreier is a senior wealth strategist for CIBC Private Wealth, US, with more than 10 years of industry experience. In this role, he works closely with high net worth clients in New York, the Mid-Atlantic and the Southeast to provide integrated wealth management services, including comprehensive estate and financial planning solutions, multi-generational legacy planning and fiduciary administration for trusts and probate estates.