Ideas in the Wild: How Bill Keen is Helping Retirees in the Second Half of Their Life

Zach Obront
Authority Magazine
Published in
6 min readSep 18, 2019

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As you approach retirement, questions begin to float through your mind that you may not be equipped to answer: Do I have enough, or will I run out of money later in life? What will happen to my spouse if I die? How do I avoid costly mistakes and maximize my resources?

At the heart of all these questions is a desire to feel comfortable once you retire. Sadly, millions of people retire each year who don’t feel this way. They’re worried about running out of money before they die, so they’re frequently stressed and not able to enjoy the moment.

Bill Keen wants to help people be better prepared for their retirement with his new book, Keen on Retirement: Engineering the Second Half of Your Life. In addition to walking readers through the steps of building a dynamic retirement financial plan, Bill tackles the psychological and emotional challenges associated with retirement that many retirees never consider.

I sat down with Bill to see what inspired him to write Keen on Retirement, what his favorite actionable idea is from the book, and how he applies the lessons he shares to his own life.

What happened that made you decide to write the book? What was the exact moment when you realized these ideas needed to get out there?

After more than 27 years of being a financial advisor, sitting in numerous private client meetings, and spending over two decades of teaching retirement literacy classes, I have seen firsthand the lack of preparedness for retirement that permeates our country today. I’ve seen planning and investment strategies that have and have not worked, the most common dangers people face, and the opportunities that exist in their lives and in the market.

I believe everyone deserves to retire with contentment about their finances and to live out the second half of their lives without anxiety and strife. We know that money is a contributing factor to fear, anxiety, and stress. It breaks up marriages and can cause all kinds of health problems. The good news is that people can work towards building the life they desire, by using just a few basic tools.

A common issue though, is that most people simply don’t know where to turn for independent, objective financial information. About four years ago, I started the Keen on Retirement podcast to make information like this available to the public. I wanted to provide a free resource for folks to learn from, that was based on the professional experience that I have gained from nearly three decades in the financial industry.

At that time, I also realized that I needed to condense our material down into an easy-to-read manuscript, which is when the idea to write the book came together. I had been encouraged by mentors and colleagues over the years, but when I started the podcast, it made total sense for me to pull my thinking together in one format to get information collectively into people’s hands. Not only the numbers and making sure technically everything is handled correctly, but also making sure people have thought about the psychology and social aspect of retirement, as well.

What’s your favorite specific, actionable idea in the book?

By far, it would be creating your Retirement Blueprint. Once you’ve gathered the facts about your assets and liabilities, it’s time to figure out what your specific objectives are. You would never build a building without a blueprint and you would never fly in a commercial airliner without a flight plan filed. It is essential to get this right because one mistake in that blueprint or flight plan can produce a cascade of problems that can be devastating.

As I like to say, what gets measured, gets done. Creating a blueprint gives you a basis for measuring how you’re doing in preparing for retirement and beyond. By establishing objectives, setting goals, and creating a timeline, you can gauge how you’re doing. You can visualize the future and work backwards so that you know if the things you’re doing today are helping you get to your desired destination, versus allowing you to drift away from it.

We must have a plan, we must be intentional, and we must be deliberate in controlling the controllable. There are so many things outside of our control in this world, but when it comes to retirement planning, there’s no excuse for not taking responsibility and controlling the things that we do have control over, and this is where the blueprint comes in handy.

Finally, on a more personal level, it can be very exciting for folks to create that blueprint. We take out a piece of paper (or a whiteboard preferably) and write down how old you will be at each of these intervals: three years, five years, ten years, and twenty years from now. We also write down how old our spouse and our children will be. This provides some real intimacy to this exercise. It can help take our mind away from the minutiae of the day and put it out into the future. What do we want our life to look like at each interval? Ideally, where will you be physically, financially, mentally, and spiritually? What is your ideal future? We don’t leave any of our hopes and dreams out of this discussion. We’re including it all in our blueprint.

This is a financial exercise, as it’s very important to understand assets and liabilities from a financial standpoint, but it also gets to the why. It gets to the reason we’ve worked hard, saved, and been disciplined, and what we’re looking to have the next half of life provide for us. We leave nothing on the field. We play full out here, and we work hard to design the life that is inspiring to us because it helps us to know and stick to the plans that we work backwards to create.

What’s a story of how you’ve applied this lesson in your own life? What has this lesson done for you?

A lot of the excitement and passion that folks hear when I talk about putting together a retirement blueprint comes from the fact that my wife and I also regularly update our financial plan, retirement blueprint, and estate plan. We know there’s power in the process because we execute the process in our own lives.

The clarity and competence that comes with being deliberate and intentional about where we’re headed allows us personally, to live each day to the fullest. We have learned that time is the most priceless commodity, so we want to be able to live our lives focused and in the moment, instead of worrying constantly about our financial situation because we haven’t addressed it.

This is what we advise our clients to do, and we are grateful and honored to have been doing it ourselves, and to pass these traditions down to our children as they come of age.

For more information, check out Keen on Retirement on Amazon.

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Zach Obront
Authority Magazine

Co-Founder of Scribe, Bestselling Author of The Scribe Method