9
Long-Term Goals

In a nutshell: Long-term planning is hard in the throes of working full time, especially alongside the demands of family. But if you don’t put some key pieces in place, you run the risk of someday asking what it was all for. Later, as you get to the highest point in your corporate life, you need to start figuring out the transition to the next stage, to a portfolio life of professional, personal, and philanthropic pursuits.

The Wake-Up Call

How many of us have marveled as we listened to distinguished colleagues or speakers talk about how they planned their career? You’ve listened to them reflecting on how one thing built on the other, from college, to graduate school, to their first job, and then on in a seemingly seamless progression.

For most of us, it doesn’t go like that. I remember listening with some frustration to Colin Powell, retired four-star general and former Secretary of State, an incredibly accomplished individual and powerful speaker, urging his audience to take the advice that had served him so well: “Always be looking for that which you do well and that which you love doing, and when you find those two things together, man, you got it.”1

If only it were that easy. Most of us do not find that what we do well is also something we love easily or early. Some never find it at all. And for others, it changes over time.

However, it’s a good maxim to reflect on, to see how close we are to achieving that goal or how far away from it we stand. If you hate what you do and are only average at it, then you really need to take a look at what you’re doing with your life.

Some people get a wake-up call, like a health scare or a rupture in a relationship, which causes them to reassess what they’re doing with their lives. But most of us don’t. Most of us move along from one year to the next, from one job to the next, making choices as we go, but not seeing a pattern and not consciously laying out a path with a destination.

Until we look in the rearview mirror and see how it all unfolded, the impact of some of the choices we make seems small at the time.

I had a colleague at the United Nations in New York who used to talk about a tactical error he thought he had made in staying too long in a particular organization, but had later concluded it was a strategic error because the role had locked him into an entire career path with limited options for exiting. The magnitude of the decision to stay became increasingly amplified as the years passed and was something he regretted.

It’s a cliché to say that no one regrets not spending enough time in the office on his or her deathbed. But some fascinating reports from older people, gathered by David Brooks of the New York Times, compiles what makes for the happiest of lives.

One of the key findings was of the benefit of dividing life into chapters, however artificial that seems. Those who did so reported feeling they had had more control over their lives and the direction they took, than those who felt they had bobbed along on an “unbroken flow like a cork.”2

Other key lessons included to be wary of ruminating, rather move onward and upward; don’t try to control others, because you can’t and it will frustrate you; and take more risk rather than less. Older people generally regretted more the things they hadn’t done, rather than the things they had done. That coincides with Dan Gilbert’s research on decision-making.3 The seniors also wrote about the pleasures of positive relationships and being a member of communities, as well as working inside organizations and crafts, rather than staying outside as rebels or lone wolves.

Dozens of older people’s life stories are gathered on Brooks’s blog and make for fascinating reading, at times harrowing and melancholy, often funny and touching.

Reading them may be enough to give you space to reflect on what you’d like to write as your life story. To help you do that, try this exercise:


Exercise: Write a letter to yourself five years from now. Write about what you’re currently doing, how your life is, what you value, and what you dislike about it. Write to yourself about what you hope to be doing in five years’ time and what you hope will have occurred in the time that elapses between then and now. If five years feels too long, then write a letter for a year out. When you’re done, seal the envelope, address it to yourself, and put the date on which it is to be opened. Place it somewhere safe, with important personal documents or inside a journal, where you’ll remember its location.


This is your own wake-up call. You don’t have to wait until you’re 70 to decide if this was the direction in which you’d like to take your life. You can do it right now.

Financial Prudence, Personal Abundance

One of the biggest mistakes people make when planning for the long term financially is being overly optimistic. We always assume we will earn more in the future and never less. Our mental trajectory is a series of salary increases and bigger jobs or a growing business. This is generally true, but definitely not a given. Circumstances change, economies and industries decline, and health issues and personal obligations intervene.

A woman I know, having attended Princeton for her undergraduate degree and law school, began her career as a public defender, a demanding but intellectually rewarding career defending low-income clients in the judicial system. She assumed she would continue in this field for some time. Then her second child was born with special needs and she found herself needing to cut back and work part-time in order to care for him. Her career has continued to be extremely rewarding; she now primarily works on death penalty cases, but her earning power has certainly been impacted and she couldn’t sustain her lifestyle without the second income provided by her husband.

Policymakers have long known about people’s unrealistic optimism about the future. It’s the same tendency that causes us not to contribute as much as we should to pension plans, to put off saving for a rainy day, and to assume the value of our homes will increase every year.

Behavioral economics is the field of study about the psychological and emotional factors of how we make decisions. More and more it is used by policymakers to make it easier for us to make decisions that are good for us, like contributing to our pension, and making it harder for us to do things that harm us, like smoking.

A useful primer in behavioral economics, as well as a fascinating read, is the book Nudge by Richard Thaler and Cass Sunstein, which collected examples of how governments could “nudge” people toward making better decisions.4

In the United Kingdom, a “Nudge unit” was set up within the Prime Minister’s office to create policies that “enable people to make better choices for themselves.” The unit also aimed to improve public services and make them easier to use, drawing on ideas from behavioral science literature. It was the world’s first government institution dedicated to the application of behavioral sciences and has since been spun off as an independent entity that operates globally.

You can create your own nudge unit by assessing which areas of your personal finances could do with decision-making that is focused on the long term.

You might want to consult a reputable financial advisor, one with fiduciary responsibility, to help you map out your long-term financial goals. Focus on the building blocks of appropriate levels and types of insurance for when things don’t work out as planned: health, life, home, disability, and so on. Then move to the planning for the future: retirement account, home ownership, college tuition for children, and the like. Set up automatic increases to pension and savings contributions. You won’t miss what you never had.

As you put little “nudges” in place, don’t think that means you’re putting on a hair shirt. You’re simply building structures that make it easier for you to get the big things right. You can still have plenty of personal abundance in your life. Abundance is a mindset, not a specific amount of money. Abundance is knowing you’ve made the right decisions in the long-term plan and you can enjoy the pleasures of life in the present.

Personal abundance is about being happy with your choices and decisions and not looking at others for validation. Abundance is not impulsive spendthrift behavior. Abundance is knowing when you can treat yourself and when you would rather stick to your plan knowing the long-term benefits that it will accrue.

If You Plan It, They Will Come

“I’ll need at least five bedrooms, and it has to be lakeside.”

The senior executive who told me this was single, recently divorced, and the property he was looking at was a 10-hour drive from where he lived. “Why’s that?” I asked.

“Because if it’s not lakeside, they won’t come in summer and if there aren’t enough bedrooms, they won’t be able to bring their kids.”

The people he was talking about were 15, 13, and 10 years old at the time, but he was planning ahead.

My friend was thinking about when his children would be grown and how he could ensure he would get to spend time with them. He wanted to make a plan that would maximize the chances of them wanting to spend time with him.

He wanted to make it easy and inviting for them, so they would factor in a couple of weeks’ vacation a year at a family place, a place where they would see their siblings, and where they could bring their friends and, eventually, their own families.

And he wanted to get a start on that now, even though he would not be able to spend much time there initially. He had a demanding job and traveled a great deal. Custody of the children was split with his ex-wife, so there was only every alternate spring break, and other holidays, and the kids went to summer camps for large parts of the summer.

Yet there he was, poring over maps and real estate listings, looking for the perfect family compound. He was searching for something that would work now but that they could also grow into.

I thought this was a better approach than one taken by the CEO of a global media company. This was someone who was listed in the top 15 highest-paid CEOs in the United States. He had been telling colleagues his plans for Christmas and New Year’s, which included flying his extended family by private jet first to Paris for a week and then on to Madagascar. He said family holidays had become more and more elaborate as he tried to keep the interest of his grown children by offering once-in-a-lifetime trips that only he could afford to provide.

By comparison, my friend looking at dilapidated farmhouses on lakes in New England is probably on to something better, in my view. By making the holiday home available to others to create their own trips and memories, he is extending the parameters for meaningful memories.

We know that experiences give us more pleasure and create more happiness than things. But experiences generally need to be planned for. It’s hard to impulse-buy a family vacation.

If that’s the case, and we are thinking in the long term about the life we want with the people we love, then planning to ensure those experiences happen becomes really important.

Great Memories, With a Little Planning

Here’s a quick way to ensure you’re taking time to create memories with the people you love:

  • Take out your calendar and look at the next 12 months. It’s easier to do this with a paper calendar than electronic (just saying).
  • Now mark the high holidays, federal holidays, and any vacation already planned.
  • Mark the places where you would like to take any additional time off, but haven’t planned anything yet. Summer next year, for example.
  • Look for gaps or long stretches where there are no holidays. Put an asterisk there. Can you take a break there? If not, those are great times to get theater tickets or plan a special dinner.

If you live with others, share the plan as a draft and get some input. Where would they like to go? What would they like to do? Then start putting some of the planning steps in place, making reservations, asking others to join you, and so on.

If you don’t plan it, it’s hard for others to join you. You also lose out on the benefits of anticipation, which we previously discussed. Remember: Half the pleasure of the trip is thinking about it beforehand.

A group of my girlfriends used to plan a small ski trip every January over Martin Luther King weekend. We would go to a local ski resort, a two- to three-hour drive at most, no flights or airlines. We would rent a house on a nearby lake, as large or small as the group needed, and pile in. Families would take turns cooking in the evening, and we fixed breakfast for children and ourselves. Lunch was on the mountain. Evenings were for board games, movies, and too much time in the hot tub. It was great fun, inexpensive, easily organized, and always very memorable. Eventually the children outgrew the resort and each other, but we still reminisce about some of the more hilarious moments: the child who wanted to move to the rental because it was nicer than his real home, the father who thought his children weren’t far enough out on the ice, and the couple who insisted we all roll in the snow after being in the hot tub.

The memories you create also need a place to live on, beyond when you get together to recall what happened. That’s easier than ever now. Take plenty of photos but make sure to upload them and turn them into photo-books, slideshows, or calendars. You can hit “auto fill” and still end up with something special. They also make a great gift for the host or friends who joined you. Now you are guaranteeing a long-lasting benefit from those moments.

Professional Legacy

A colleague, who retired after 30 years at the same institution, was beloved. He had worked in many parts of the organization and held the number-two position, effectively COO, at the end of his career. He had even been acting CEO for the final few months before he left. There had been some talk of him possibly getting the top job, but he didn’t. Instead that role went to an outsider, found by recruiters and vetted by the board. Whether he had even wanted the top role was uncertain, but he likely had.

At his leaving reception, amid the funny anecdotes and remembrances of some crazy trips to crazy clients in the “old days,” much of the talk was of the fact that he was going to be replaced by two people. His job was effectively being divided into two, and two people would split the portfolio of responsibilities that he alone had managed.

The conversation was not one of wonder and admiration that it would take two people to fill his shoes, but rather that it was hardly surprising that no one would want his job, at least not all of it.

My colleague had been famous for being completely devoted to his work to the exclusion of all else. He was there early in the morning and late at night, at every committee meeting and board meeting. He knew the details of every major transaction that was ever undertaken, and although he took vacation in the summer, he could always be reached by email, no matter the season.

If he had a professional legacy, it was one of courtesy and a sense of humor, of a fine intelligence, but perhaps above all of enormously long hours and hard work.

A professional legacy is how your colleagues and peers will remember you after you’ve gone. What do you want your legacy to be?

The time to think about your professional legacy is not when they’re planning your farewell party. You need to think about it much sooner—not from the beginning of your career, which is probably unlikely unless you’re a savant with unusual skills and have always known what you want to do.

If you’re like most people, you’ll stumble along gradually getting better at some things, realizing that you’ll never be great at others, and that there are a few things that you are really good at and hopefully also enjoy. That dawning usually coincides with a greater understanding of yourself, the good and the bad.

Thinking about your legacy can be useful at any time because it focuses your mind on what really matters to you.


Exercise 1: Jot down what you’d like to be remembered for by your colleagues. Try to imagine you’re writing the talking points for the host of your farewell reception. What are the qualities and achievements you’d like them to be describing when they talk about you?


Think about your heroes. That’s what Marshall Goldsmith did in an exercise run by Ayse Birsel.5 Then he was challenged to be more like them.


Exercise 2: Write a list of your heroes, personal and professional.

Now write down their attributes. What were their chief characteristics?

Now cross out the names of your heroes and replace it with your own.


Here’s what Marshall Goldsmith discovered: Each of his heroes had been extremely generous and a great teacher. To be more like his heroes, that’s what he needed to be. That’s why he began his 100 coaches project, in which he teaches 100 coaches everything he knows, for free, and ask them to pass it on.

Having done Exercises 1 and 2, you now have the road map for your professional legacy. Time to take action to secure it.

A Portfolio Career

I am often asked to help clients who want to build portfolio careers. Sometimes a firm will ask me to help a senior executive who will be retiring. Sometimes it is an individual who wants to position themselves for the next phase.

What exactly is a portfolio career, and how do you create one?

Let’s assume you have had a great career and are currently in what will probably be your last full-time role. You are a little tired of corporate life and not really ready to retire but you don’t want or need another full-time role. You know people who are serving on boards and acting as advisors to big-name firms. That looks attractive.

How do they do that?

The secret to building a successful portfolio career is being purposeful about creating it and clear about what really interests you. The old maxim of finding what you’re good at and what you love applies here.

About 12 months before you are due to retire, go through your contacts and create a list of people who know you and could recommend you. Start calling them. Be transparent with them about what you’re doing. That will make it easier for them to help you.

Develop a script: “We haven’t spoken for a while. I wanted to let you know that I’m going to be stepping down from X, and I’m interested in board and advisory roles. I thought you would be a good person to advise me on that. Do you know of any? Would you be willing to recommend me?”

Then follow up. Set up meetings, coffees, and lunches. Talk to people. Talk to more people. Keep an open mind, but also keep your eye on the type of role you would ideally like. Don’t commit to anything too fast, unless it’s a dream role. Explore.

The best people to recommend you for board seats are peers or people senior to you in your industry. The second best are headhunters. Call the ones you know. If you don’t know any, make a list of the big ones. Call them and ask to speak to the head of your industry’s practice. Try to meet in person if you can.

Build your profile in your last year. Go to conferences, preferably as a speaker. Write about current topics in your industry for trade outlets. Update your LinkedIn profile. Get a decent headshot. Update your resume and get it laid out professionally.

Get a coach. This process is much easier if done with an experienced professional rather than on your own. My own clients speak highly of their experience:

“Corrie was an invaluable partner in my transition from public to private sector and move into the next phase of my professional life. With her supportive, direct manner she helped me discern between what I wanted to do and what others wanted to me to do, and to negotiate the various contracts and arrangements that constitute my professional life today. I highly recommend her.” —Evelyn N. Farkas, PhD, Former Deputy Assistant Secretary of Defense, United States

Important! Do not spend 100 percent of your time doing your current job. It doesn’t matter how important it is or how busy things are. You should have built capacity for others to pick up your load. You need to be spending at least 20 percent of your time on building your new career. They will survive without you. Take care of your people, but make sure you don’t do that at the expense of taking care of your future.

Follow this guidance and you will find you can easily turn your portfolio career into a portfolio life and enjoy its benefits and freedoms.

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