Are You Truly Ready to Retire? Unpacking More Than Finances

  • Home
  • Videos
  • Are You Truly Ready to Retire? Unpacking More Than Finances
Play Video


Are you ready to retire? This miscalculation or misjudgment could cost your retirement, but let’s put the calculator away. I didn’t ask if you could afford to retire; I asked if you were ready to retire. Hi, I’m Hunter Brockway, father of Boke Retirement Strategies, here to help set you up for a successful retirement while spending more and avoiding being killed in taxes. The answers to this question start before we break out the calculator. Unless you’re the number-crunching engine type, I’m sure you’ve known your numbers before you even left kindergarten.

First, I ask, “What does money mean to you?” And to your answer, I ask, “Why is that?” And to that answer, I ask again, “Why is that?”

Next, “What does retirement look like to you?” Close your eyes and paint the picture. Seriously, I’m not one to be ritualistic, nor am I asking you to be, but close your eyes and imagine day one of retirement in color. What does it look like? What time do you wake up? What do you do? Draw this out as long as you can.

Next, I’m going to suggest drawing out what matters to you. I’m going to put on the screen here an illustration that we drew up from George Kinder’s Seven Stages of Money Maturity. Feel free to pause this video, create your own, or email us to get a copy. This exercise helps to sort out obligations and desires. Fill out the cells accordingly, however you feel fit. In the “Got to” column will be things as if your soul could not exist without this. “Have” refers to possessions, and “Do” refers to accomplishments and activities. “Be” covers your state of existence. In the next column, “Should,” this covers what you feel is an obligation. In the “Like” column, put the extras and fluff.

Listing out likes for the brain to see can often be eye-opening, help prioritize your life, and clear your head. As you build this and visualize your life goals, you will find the rest flows naturally. Ideally, this exercise will help to guide you to a more fulfilled retirement or path to retirement.

Now that you can start to picture your retirement, what if you took a practice retirement? Live life like you were retired, with the ability to go back to work. Can you take a leave of absence or use up stockpiled vacation time? Or do you have the ability to cut back on responsibilities and work part-time? Could you take a demotion to work less but have more time for yourself? If you’re considering retirement, I imagine you’ve been working in your field of profession for a while. Could you do some level of remote work or part-time consulting work?

The overarching point of all of this is that it is important to retire to something and not from something. I’ve seen clients go both ways. I’ve seen clients work too long because they couldn’t pull the trigger on retirement, even when they could afford to, whether that decision was emotional or just how they thought it should be. I have also seen clients retire too early just for the sake of retiring.

Take action: Put a time block in your calendar to sit down with your significant other, turn off the phones, and imagine your retired life together. You’ve worked your whole life for this. I’m Hunter Brockway, founder of Boca Retirement Strategies. If you would like to experience how we help our clients get the most out of retirement without running out of money, you can book at no cost, no obligation call on our website at or email us at We are based in South Florida, Western Massachusetts, and work with clients scattered throughout the US. Enjoy your successful retirement, and thank you for watching. Bye.

8 Questions to Ask a Financial Advisor

Are you asking the right questions to secure your financial future? Gain access to our free guide on what to ask a prospective financial advisor by filling out the form below.

This field is for validation purposes and should be left unchanged.