Retirement Starter Pack: Questions to Ask Now for the Retirement You Want Later

Aug 1, 2023

Someday (if you haven’t already) you will hand in your badge, hang up your hat, close your accounts, and say your goodbyes.

Retirement is exciting and bittersweet, but if done right, it also requires strategic planning.

We’ve compiled a handful of our best questions and resources to help you consider what you want and need in your next phase of life. Use these tips to craft a retirement full of your favorite things: family, friends, travel, hobbies, rest, and freedom from financial worry.


1. Take a moment and picture yourself XX years from now. You are 70 and enjoying a comfortable retirement. 

  • What are you doing?
  • What does it cost to do everything you are doing? (Hint: It will probably be more than you think)
  • If the cost is more than your current earnings, what will you cut out of your current standard of living to achieve that level of spending?
  • And where is the money coming from?

These answers are unique to you. Some have the means and desire to spend early on travel or family, cutting back and securing part-time jobs as they get older, and others want to pace themselves and enjoy the consistency of regular spending. The key is to talk to an expert about your options and enter retirement with your eyes wide open.

As you plan, review “Five Financial Rules of Thumb: When They Work and When They Don’t.”

2. To what extent do you want to intervene in the financial lives of your loved ones, either during your lifetime or as a legacy to them? 

This could include regular support for your children, education for your grandchildren, or long-term care for your parents. Before you retire, decide how you want to help your family and friends. If you don’t know how much you can give, talk to an advisor.

These “4 Ways to Help Your Loved Ones Succeed Financially” are another helpful starting place.

3. What’s your desired legacy? 

Get specific about your legacy plan:

  • Is there a particular institution – a church, a school, a charity – that means a great deal to you and to which you would like to leave a meaningful legacy?
  • Do you wish to leave a legacy for your family?
  • Do you have any other notes about how you would like your estate distributed?

An estate plan is a key component of an overall financial plan, especially as you enter retirement. Review and avoid the “5 Common Confusions About Wills, Trusts, & Leaving a Legacy.”

Also note that multigenerational tax planning and charitable giving are important when selecting “The Best Retirement Account: Retirement Accounts 101.”

4. What concerns do you have regarding health care for yourself? 

Think through the long-term care of your parents and family. What did they need as they aged? What do you anticipate needing for your long-term care?

This is a hard conversation, but imagine the relief you’ll feel if you prepare now.

Even in the unexpected, the right plan won’t fall apart. As we say in our article on “How to Build a Resilient Retirement Plan”: “Our planning creates contingencies to help us through the hard times – whether it be market events or life events, such as health changes or job loss.”

5. What are your financial goals and hobbies in retirement? 

  • Do you have any specific financial goals, such as purchasing a different home or a new vacation home, funding a wedding, buying a car, traveling with family, etc.?
  • Which hobbies do you find take the most money to support? Do you plan on increasing your time with these hobbies in the future?

This is the fun part! What are your retirement dreams and plans? How much will they cost?

One way to potentially save money and have more to spend on your goals is to optimize your taxes. Check out our article: “3 Ways to Make Taxes Easier in Retirement.”


No one article can cover anything and everything you might need for your unique retirement plan, and it certainly won’t ease the headache of never knowing for sure if you can do what you want to do.

Working with an expert is a great way to check all the boxes on your retirement.

If your plan feels shaky, or if you’re just looking for a second opinion, reach out to our team at [email protected].



By Brian Remson, CFP®

Schedule an appointment with an advisor in your area.