The stories in Retirement Fail are based on actual scenarios and events; however, names and identifying details may have been changed to protect the privacy of those discussed. In some instances, composites have been created.

This book is offered as a resource for informational purposes only. The information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and may not be suitable for all investors. Always consult your own financial, legal, and/or tax advisor before making any decisions related to your investment, tax, estate, or financial planning.

To ace retirement and not fail requires discipline, effort, a little luck, and a lot of wise guidance along the way. The same goes for writing a book. That is why I am so thankful for all the people who have guided, taught, and influenced me during this journey.

My Mom and Dad had the greatest influence on me, encouraging me in ways they may never know. I reference them in the book many times because I learned so much from watching the way they handled tough times and good times, both personally and financially, and talked openly about money and finance while I was growing up. So, Mom and Dad, a big thank-you for your guidance, unconditional love, and support.

I am fortunate to have great siblings and a fabulous brother-in-law, and we are all so close that they allowed me to share stories about them. I know they are very thankful for the stories I left out! Thank you Gail, Bill, Pam, and my brother-in-law Frank, for always being there for me!

Twenty-seven years ago, three men and a lady decided it was time to start a business that focused on providing objective, independent advice to individuals and families without the concern of self-dealing and conflicts of interest. We all took a leap of faith – a lot of faith, because our new job couldn't afford to pay us a salary – but we had a strong belief that we would change the way people receive financial advice, and we aced it! To Jim Bruyette, Pete Speros, and Eleanor Blayney, I will forever be grateful for your leadership and for being patient with me. Most importantly, thank you for making this journey so much fun and for your friendship, which I will always treasure.

At SBSB we have an amazing team of professionals, and this book would not have come to be without the help and inspiration of the whole group. Together as a team, we make a difference in our clients' lives and in the lives of one another. You have all been a part of the stories in this book and the millions more that I haven't written about. To our entire team at SBSB, I want to say thank you for your passion for excellence and your amazing desire to serve our clients with the utmost integrity and respect.

I want to give special thanks to several SBSB partners and colleagues: Kris Andrejev, Jim Bruyette, Patrick Dunne, Gary Ingram, Martine Lellis, Jeff Porter, Barbara Schelhorn, Pete Speros, and Karen Tovey. These advisors gave freely of their time (often their lunch hours) and expertise, agreeing to be interviewed, sharing their experience, and providing indispensible context for the book.

Friends and colleagues in related businesses also offered critical background and shared their stories of attending to clients' special insurance needs. Thank you to Diane Beatty, Virg Cristobal, Stafford Jacobs, Jon Katz, and Kim Natovitz for your generosity in sharing your stories and advice. And a special thank-you to Mark Tibergien, a great friend and mentor, whose wisdom and guidance over the past twenty-five years has been invaluable. Thank you, Mark, for introducing me to Wiley and for your keen insights for this book.

We are so blessed at SBSB to have clients who care about us as much as we care about them. Although it is not appropriate to name any of them here, I want to thank our clients for making this book possible. The stories we share make the situations real and provide tremendous guidance and insight that others can learn from. Thank you to all our clients, who make going to work every day a true joy.

In writing this book I was thinking about how to help people open up and have conversations with their partners and their advisors in areas that are often sensitive, and to provide stories and content that was relevant to creating a successful retirement. I wasn't thinking about marketing. Fortunately, I have Katie King, Caitlin Norton, and Jeanne Rossomme to think about that for me. Your ideas have helped me understand how to share the book and the stories through social media and other means. Thank you for all the guidance and advice on how to get the word out and for your thoughtful comments on the book's cover and the initial manuscript.

One of the core values at SBSB is “Lifetime of Learning.” Out of necessity, in the early 1980s, much of the learning was OJT (on-the-job training). But there was also a group of advisors, passionate about financial planning, who met regularly to share ideas and learn from one another. We eventually formalized the group and named it the Alpha Group. I am proud to say the group today includes many of the most respected and influential leaders in the wealth management profession. A couple of us then brought together a group of leading CEOs in the field and created the Blind Squirrels, a group of entrepreneurs focusing on all aspects of building a great business. The value these two groups brought to me and our profession is immense. Thank you all for sharing your wisdom and experience. I learned from you how to be a better advisor, leader, and CEO.

This book would never have made it to reality if it weren't for Caitlin Norton and Susan Lauzau. I gave Caitlin a tough task: Help me find an experienced professional who knows the book writing world and who can guide me and help me turn my ideas and stories into a book people will enjoy reading. Caitlin did her research and introduced me to Susan Lauzau, a fabulous writer, talented editor, and genuinely humble person. Susan, you have a special gift for creativity and a wonderful ability to endure my endless ideas, changes, and rewrites. You helped make this book real and fun to read. Thank you for keeping me on task and on time. Thank you, too, for your invaluable guidance and for making this an amazing journey.

My kids, David and Lisa, bring me incredible love and joy, and I want to thank them for letting me share a few stories about them in the book. What child wants their dad writing about them and publishing it to the world? Thank you, David and Lisa, for being amazing kids, for all the great adventures we have been on together, for the challenges we have faced together, and most importantly for being my best friends.

Writing a book over an extended twelve-month period while running a rapidly growing company full time requires a lot of TLC and patience. Not from me, but from my loving and caring wife, Pam. Thank you, Pam, for being simply fabulous and wonderful and patient with me throughout this process. Thank you for reading and rereading the many drafts. Thank you for encouraging me along the way and for your love and support. Despite all the hard work over the past twelve months, we still managed to have a lot of fun! I love you.

What causes a retirement fail? That is, why do people who have prepared for retirement end up unable to fully enjoy the thing they worked so hard for? I have thought about this question a lot. Most people believe that it's due to poor investments. But I cannot recall a single instance in which investment performance has been the cause of a client losing financial independence or failing to enjoy the life in retirement that he or she desired.

I joke with my clients that, rather than portfolio performance, it's usually the things you have to care for that weigh more than 50 pounds that wreak havoc on retirement finances: Grown kids, houses, horses, cars, boats. Clients laugh with me, sometimes because they have already made these mistakes – or, more often, because they are wondering which decisions down the road will impact their own retirement. What do you think can trip you up in your post-work life? Will it be your finances, health, family, a divorce, a scam? The list goes on.

Retirement Fail is not about going broke or becoming destitute; it is about the personal, emotional, and financial decisions you make that can disrupt the life you could have enjoyed in your post-work life. Whether you have $500,000, $5 million, or $50 million, the issues we discuss are real and relevant, not only for you but for your children and other family members.

I talk with my clients about how to plan for the evitable, for the things you are capable of avoiding. People focus on the inevitable – what will happen, no matter what – and that's important, too. But we humans may be tempted to throw up our hands and leave to chance the very things we truly can control, those we should be taking thoughtful and deliberate steps to avoid. We sometimes court retirement fail.

A Kernel of an Idea

In the fall of 2014, Evan Simonoff, editor-in-chief and editorial director of Financial Advisor magazine as well as editorial director of Private Wealth magazine, called me and asked me to speak at the Inside Retirement Conference, which focuses on current topics that affect retirees. He asked if I could speak on using income-generating assets for retirement in a low-interest-rate environment. “That is a great topic,” I told Evan, “but what I would love to talk about is how people fail in retirement.” No one is talking about this issue, I told him, though 10,000 people are retiring every day. I shared that I had nine reasons I have seen people fail in retirement, and that the best way to avoid those failures was to get the conversation going early. Evan didn't hesitate for a second: “I love it…that's your subject,” he told me.

Every day, I and my colleagues at Sullivan, Bruyette, Speros & Blayney (SBSB) talk with our clients about decision making in retirement and in the lead-up years. And while we discuss investments, how to best allocate portfolios for cash needs, taxes, and other related items, most of our energy goes into discussions that are far thornier. These conversations can be delicate because they often involve a person's most deep-rooted wishes, fears, or insecurities: Maintaining his or her role as provider for the kids (even though the children are in their 30s); recovering one's identity after exiting the professional world by starting a business (even a high-risk business like a trendy restaurant or a vineyard); or buying that dream vacation home (even though it might not be truly affordable).

The topic struck a nerve – the room was packed, and other advisors came up to me after the conference, wanting to learn more about how to have these important discussions with their clients. Evan later wrote a piece for Financial Advisor based on my talk and our conversations, and that, too, generated a lot of buzz and comments from other financial advisors. And the more I thought about it, the more I realized how critical the emotional part of retirement planning and decision making truly is, and how much my clients and others like them could benefit from a guide to take away, with stories that underlined the realities of some common retirement fails.

Are You Talking to Me?

There are plenty of books about how much money you need in retirement and how to save and invest your cash. This is not one of them. I wrote Retirement Fail for those of you who have been preparing for retirement financially but need some guidance to ensure that your plans for a happy, healthy retirement are not compromised. Ready or not, you will be making decisions that can positively or negatively impact your financial future. You may be on track with savings goals, but there are potential pitfalls ahead, and the deepest pits are the ones you don't even see or, in some cases, those you would rather not acknowledge.

Many people have good, strong financial plans, but they don't necessarily notice themselves getting caught up in troubling patterns – or they may be surprised by an event they didn't see coming. The numerical side is one thing; an advisor can easily come up with numbers and projections. The more difficult thing is to look at the way the decisions we all make impact our own future and those around us. Retirement Fail shows you the watch points you need to pay attention to and helps you think through what your priorities are – and what trade-offs you may have to make to reach your goals.

If you're working with a financial advisor – and a Certified Financial Planner Board of Standards (CFP Board) survey indicates that 40% of Americans are now consulting a financial professional¹ – you can use this book to help start productive conversations with your advisor. You don't need to stick to the technical investments and hard numbers – as you'll see from the stories in Retirement Fail, we see lots of different scenarios and can offer suggestions for handling many complex issues related to individual and family finances.

We like to share stories, both those of clients (all carefully anonymous, of course) and from our own lives. Money is one of those things people often don't talk about with their friends. That's why stories are so powerful – it's why we use them in our meetings and why I use them throughout this book. We can say, “We know another person who was in your exact spot, and this is what he did.” Everybody likes confirmation or affirmation that they are making wise decisions, or that others faced similar situations and came out on the other side. We can learn from others' successes and take warning from their losses.

Where's the Advice?

My parents dropped me off at the main campus of Penn State University in September 1975. I was surrounded by mountains (locals call the area Happy Valley) and by 30,000 other eager, energetic college students. Mom and Dad took me out for lunch before they left, and my dad asked me what I thought I was going to do when I graduated.

That was an interesting question for a freshman who had not yet been to one class. But I was one of those rare freshmen who actually did have an idea of what I wanted to do. I had loved reading about stocks and different businesses since I was young, so I said, “I am either going to work on Wall Street and help people with their finances or I am going to be CEO of a company and run a business.” Without skipping a beat, he said, “The smartest people I know in business are CPAs [certified public accountants]. You should get a degree in accounting.” Being a bean counter had never crossed my mind – I wanted to help people with their finances and investments.

My father's words stuck with me, though, and when I graduated with a degree in accounting I went to work for Ernst & Whinney (now Ernst & Young) in Washington, DC. After a couple of years in public accounting, I left and joined a local brokerage firm as a financial planner, following my real passion.

Excited about the job change, I called my parents to tell them of my big move. Dad, a bit shocked, said, “Why would you leave a great career in public accounting to become a salesman?” When I told him I was going to be a financial planner, not a salesman, he replied, “Every financial planner I know is just trying to sell me something.”

I thought he didn't know what he was talking about. I had this vision of helping people, not selling to them. But darned if he wasn't right. A few months after I started my job, I went to the national financial planning conference. There were several thousand attendees, and everyone I met was selling something: Insurance, annuities, heavy commission-based mutual funds, private partnerships, and so on. Where was the advice? Who was helping people make smart financial decisions?

I was fortunate in my new job, and one colleague in particular, the late Dave Dondero, took me under his wing and helped me learn how to prepare a financial plan driven by a client's goals and financial capabilities. I taught classes, wrote case studies, and became the in-house expert on tax and financial planning strategies. Most of the people at the company used my work to sell products, but I was learning the craft and building a reputation for providing quality advice.

In 1988 I decided to start my own independent firm, Sullivan Financial Consultants, with the goal of helping clients make smart financial decisions, untroubled by conflicts of interest. Then, in 1991, I was fortunate to partner in a new enterprise with Jim Bruyette, a former colleague of mine from Ernst & Whinney, Pete Speros, and Eleanor Blayney. We all shared the same passion – to help clients make smart financial decisions and to be independent and conflict free. We would provide the advice. We would help people make sound decisions about their finances.

Which brings me back around to the reason I wrote this book – and, more importantly, to the reason you are reading it. At the heart of retirement planning is the question: What is most important to you in your post-work life and how can you translate that into your day-to-day living and decision making? Once you know the answer to that question, you can frame your decisions so that your assets are truly working for you and your spending is aligned with your values and objectives. Retirement Fail helps you answer that essential question, addressing the nine ways you are most likely to compromise your retirement (and visit RetirementFail.com for more information and tips to help you succeed as you move into your post-work life). Armed with a sense of your values and goals – and a true awareness of the challenges that may lie ahead – you can craft a plan that lets you ace your retirement.