2
Destination, Not Daydream

In a nutshell: Clarify your ideal state. If you don’t have a clear destination in mind, it’s going to be hard to get there. Don’t limit yourself by what you think is possible. In an ideal world, what would you be doing? Defining the ideal future and comparing it to the present brings into reality what needs to be changed and ignites the engine for forward motion.

In October 2016, I was speaking at a conference of corporate treasury professionals in Orlando. These individuals are the unsung heroes of the financial world, the people dedicated to the long-term financial health and sustainability of their companies. The businesses in which they work include all sectors of the economy, but they rarely make the headlines. They are long-term planners and think in three- to five-year funding cycles and often much longer.

Yet, when it came to planning their own careers, the topic on which I was speaking, they admitted they were much less diligent.

It’s hard to achieve your goals if you don’t have any.

That seems so obvious, yet the vast majority of the 500 people in the audience that day acknowledged they didn’t have concrete goals for themselves despite a desire to realize change and progress in their lives.

You need to start by clarifying your ideal state. If you don’t have a clear destination in mind, it’s going to be hard to get there.

Sketch the Scene

Jo Peart, a native of Counties Dublin and Kildare in Ireland, had studied international marketing at college. It was a competitive course and many who applied were disappointed when they didn’t receive a place in the program. The job prospects for graduates were considered good. After a year of studying in France as part of her degree, Jo was now also fluent in French. She began a career helping international companies expand into new markets, something she really enjoyed.

But around age 40, after a number of successful years in corporate life, she began thinking about the future and what kind of contribution she would be making with her life. She decided that she really wanted to be in medicine and wanted to retrain as a doctor.

“I did it because I had always remained interested in medicine, in particular the provision of health services and health policy. I hate talking about things rather than taking action, and I know from corporate life that the most effective cultural change is from within,” Jo told me.

She was surprised by the almost unanimous support from her friends and family and by the number of friends that had also considered going back and doing the same. It was those in medicine who questioned her decision to leave corporate life, where she was already earning substantially more than many of her peers, in order to be a student once more at the beginning of a daunting training program. Jo didn’t see it that way at all.

“I did it because I could. I hadn’t been pining; I enjoyed work always and as I had been lucky enough to grow in confidence. I was in a position to become somewhat successful and chose to follow a passion and a vision rather than a long-lost dream,” she said.

She began medical school, and after completing residencies and internships—seven years after making the decision to retrain—she began working as a doctor. She now practices internal medicine at Connolly Hospital. She has never regretted the decision or regretted starting on a different path earlier.

“I was extremely fortunate to do the degree I did because of the friends it gave me and the career choice I made. I don’t regret it at all. For a young person making a choice out of school, medicine is a very confining career; I’m glad I came to it after my other experiences,” she said.

Jo’s is an unusual case, but many of us spend years doing things we don’t really enjoy because we think it would be impossible to change.

We worry we won’t make as much money or will lose the security of our present situation. We think we might fail and, really, where we are is not so bad.

We rarely think we might be better off. We might be happier and actually earn more. We forget about the fact that change will come to our current situations. It won’t remain static. Changes we can’t foresee will make our current life less satisfying, and we become like the frog in increasingly warm water that doesn’t notice the temperature is getting hotter until it’s too late.

One way to avoid this is to write down your ideal future state. How would you like things to be in an ideal world? Assume no constraints for the moment. What would you ideally like to be doing? How would you be spending your time?

Most importantly, write it as though it was already real. Write it as though you are already in the future and you are describing your life.

---

Exercise: Starting at the top of a clean page and write down your ideal future state. Pick a date in the future. Now write the qualities of how your life is at that future date. Use adjectives to describe how you feel, the texture of your life. What about the people who are most important to you? How are they? What are they doing?

---

Don’t limit yourself by what you think is possible. In an ideal world, what would you be doing? Writing it down and being ambitious about it is the first step to making it a reality.

Present-Day Reality

Now it’s time to compare your ideal future state with your current reality. What does your current world look like? Be very factual and objective. Use short, concise sentences. Focus less on how you feel about current reality and more on the actual facts of your situation.

---

Exercise: At the bottom of the same page, write your current reality. Note today’s date. Where do you work, what’s your marital status, do you have offspring, what is your financial situation, and so on?

---

The idea here is to juxtapose your current state with your future state. By contrasting the two states, you create structural tension, and that tension gives you the impetus for action.

This is a technique pioneered by my good friend and great teacher Robert Fritz of Newfane, Vermont. If you’re interested in learning more, I recommend his book The Path of Least Resistance for Managers.¹

As Robert likes to say, reality is an acquired taste. But being more honest with yourself about your current reality is important, especially if you want to change it.

Now compare the two states: your current reality and your desired future state. Are they a million miles apart? Or are they not all that different? Maybe the desired future state seems unrealistic given current obligations and external realities.

For example, if your future ideal state is working less and spending more time with your family, you may look at your current reality and think it’s not practical to quit your job or even cut back. You may also not be willing to change jobs to something less demanding that would mean a pay cut, so where does that leave you?

Don’t give up. The most important thing is to be clear on the difference between the two states. The contrast is what helps you. You want to be really clear about your ideal life and where you are now. That allows you to see the differences and see what you could start changing right away.

I recommend practicing this technique with smaller things in order to become fluent in it. For example, take an important upcoming meeting, a presentation you have to give, or a trip you’re going to take. You can also do it for dinner parties or projects at home. I always use it for planning Thanksgiving lunch, for example.

Here’s the next step. After you have your ideal future state at the top of the page and current reality at the bottom, start filling in the middle of the page with tasks and things you need to do to move from one state to the other.

If you find it easier to practice this with something smaller than your life, do that.

You should have a column labeled “What” and one labeled “By When,” in which you set a date for each task. The following is an example for an upcoming presentation.

This may feel like a glorified to-do list at first, but there is something magical that happens when you juxtapose the reality you’re in with the reality you desire. You will find that ideas arise out of things to do or people to talk to that wouldn’t have come to mind by simply creating a list.

Defining the ideal future and comparing it to the present throws into relief what needs to be changed and ignites the engine for forward motion.

Mind the Gap

“Mind the gap” is the famous message repeated daily over the public address system on the London Underground, the world’s oldest underground train system. It warns commuters of the gap between the platform and the train into which they are stepping. It has inspired T-shirts, mugs, and other souvenirs for visitors to London.

It’s a good metaphor for the gap between the reality in which we live and the future state to which we aspire. If we pay attention to the gap, it becomes much clearer what we need to change.

Sometimes the gap feels immense. When my son was very little, the gap between what I was doing and what I wished I were doing yawned like a chasm. Although I had an interesting, well-paid job, it was very demanding and I often felt like I didn’t want to work at all. I thought it would be lovely to press pause and simply take a couple of years off. I imagined picking my son up from nursery school every day and us hanging out together in the afternoons. At the time, his nanny got to do that while I went to work every morning and came back in time for dinner and bath time. But I didn’t have the luxury of not working. I was a single parent. Even working part-time wouldn’t have paid the bills we had.

As he grew older, my vision for what I most wanted to do changed. He was now in school all day and starting to get involved in afternoon sports. He wouldn’t have been hanging out with me even if I had been free. I realized that what I wanted most was to work for myself. I wasn’t sure how or what I would be doing, but I wanted to have my own business.

It took several more years and a change in my immigration status before I was finally able to hang out my shingle and set up my own consulting practice, but it was worth the wait. I didn’t regret not doing it sooner. It hadn’t been practical sooner. I had gained a huge amount of valuable experience in the interim and built up a powerful network of contacts. Now was the right moment to put that to work helping my clients.

It was hard work initially, and I made plenty of mistakes. Doing everything for the first time is exhausting, the first time. The second time, it gets easier. The third time, it’s easier again and you know what to do. Then you start adding more new things and it’s exhausting again, but you have a sense of momentum and you know where you’re headed. You try to enjoy this phase of building the business and not be afflicted with the feeling that you will only be happy “when” you have more clients and “when” you have more incoming calls than outgoing ones.

Then, almost a year to the day I started my business, I got sick. I was diagnosed with ovarian cancer in February 2016. My world reeled. Just six weeks earlier, my sister Barbara, who is nine years younger, had been diagnosed with breast cancer in Dublin. Unbeknownst to us we were carriers of the BRCA1 gene, a gene mutation that causes an extremely high risk of breast and ovarian cancer in women.

We hadn’t known about the gene and didn’t have relatives with breast cancer. But it seemed it had traveled down on my father’s side, concealed by the fact that he had no sisters, likely passed on from his mother who had died at home after an illness in the 1940s when he was very young. We now realized she had probably died of ovarian cancer.

I, on the other hand, was fortunate to be living in the 21st century in the United States and was treated quickly and expertly by some of the best doctors in this field. I am incredibly grateful for the care I received.

One of the many interesting things about facing my own mortality much sooner than anticipated was realizing that I was in fact living the life I wanted. I didn’t regret having set up shop by myself. I didn’t pine for the security of my salaried position and sick leave allowance. Being an entrepreneur was exactly what I wanted to be and being ill actually reinforced that fact.

I realized that if things didn’t work out (a euphemism of some understatement), I would be happy knowing I had at least started doing that which I most wanted to do. I would have no regrets. That’s the benefit of looking at the gap.

Go, No Go

Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative, there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one’s favour all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamt would have come his way. —W.H. Murray²

This quote is often misattributed to Goethe, the German poet and writer, but in fact William Hutchison Murray wrote it. Murray was a Welsh mountaineer and writer who served in the British army in North Africa during World War II. He was captured there by the Germans and narrowly escaped death by bonding with his captor over a shared love of mountain climbing. He survived three years in prisoner of war camps where he wrote the first draft of a book called Mountaineering in Scotland on toilet paper.

The quote is often misattributed to Goethe because Murray goes on to quotes lines from Goethe’s play Faust: “Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it!”³

Many people who embark on new initiatives and ventures talk of the coincidences and chance encounters that then ensued, helping them toward their goals.

We tend not to think of Providence having a role in our daily lives yet we are familiar with the coincidence that happens when we come across something for the first time, a new word or phrase, for example, and then we start to see it in multiple places, despite never having seen it before.

The Providence Murray speaks of is propelled by action. The first step and the commitment to the endeavor set things in motion. Goethe urges us to “begin it” and that once begun, magic will be unleashed. Entrepreneurs and leaders often talk about the first step that launched their businesses or signified a turn in their careers.

I’m not talking about being reckless or foolhardy. There’s no need to abandon your home and family to set off on that long-dreamed-of cross-country road trip. Nor am I suggesting you quit your job today to start your own business. (Although, if you don’t have those commitments and want to do that, what are you waiting for?)

The purpose of getting clear on your future state and comparing it with your current reality is to make it clear what you could start doing today. You should be able to see some of the steps you could take that would bring you closer to your goal.

The very act of committing to the goal and beginning to move toward it starts to generate energy and other ideas. As you begin doing some of the smaller things on the list of actions you created, you will start to see other possibilities emerge.

Sometimes what emerges is the realization that this may not actually be what you want. As you move even closer to the goal and the reality of what it might mean, you may discover it’s not really what you want or not as you imagined.

Crunching the numbers on financing a new project and mapping out the tasks needed to get there can have a sobering effect. Just as much as action and boldness bring about momentum toward a goal, they can also clarify that for right now, you’re not ready to commit. But, if you are ready, there is no better time to start than now.

There is a tide in the affairs of men.

Which, taken at the flood, leads on to fortune;

Omitted, all the voyage of their life,

Is bound in shallows and in miseries.

—William Shakespeare, Julius Caesar, Act IV

The Alternative Future

Dan Gilbert, a professor of psychology at Harvard University, has done some really interesting work on how we make choices and how we think about the future. His book Stumbling on Happiness⁴ is a terrific read. In it, he uses science to show how terrible we are at imagining the needs of our future selves and what will make us happy.

Gilbert explores how we make decisions—everything from how we decide what to order at a restaurant to whom we should marry. He proves that we are as poor at predicting the future as we are at remembering the past. His most provocative recommendation is that we should not rely on our imagination to make decisions but rather on the use of surrogates. In other words, we should look at the experience of people who have done the thing we are thinking of doing in order to judge if it would work for us.

Gilbert also points out that we don’t do that because we all believe our own situations are unique. In fact, we are not as special as we think we are and we can learn a lot from what has worked for others.

If that’s the case, it makes sense for us to talk to people who have done the thing we most want to do.

My executive coaching clients invariably hold very senior roles in their companies. Among those looking to make a transition, the most successful are the ones who get lots of input on the transition. That doesn’t mean they wander around telling everyone they meet about their plans or their desires to move on from their current roles. It means they do a lot of due diligence and research about the changes they want to make and take action to get information.

The following are six things they typically do, none of which involve telling the world they are looking for a change:

1. Map out the pros and cons of the current position, if the transition is voluntary.
2. List key influential people to ask for advice.
3. Draft a timeline with deadlines for doing research and making decisions.
4. List all of the factors, both external and internal, that they are aware of.
5. Schedule time in their calendar for research and meetings.
6. Identify who is doing the type of role they want and how they can get introduced to them.

My most successful clients are diligent about making time for this even though it can be very difficult when your current job is demanding and you have a full plate on the home front. If you can take even 15 minutes a day to work on this, you’ll be amazed with the results.

Call this time “Future Me,” and put it in your calendar as an appointment. Mark it as private if someone else sees your calendar. Pull out the previous six points and see how you can move them forward. Set a goal of reaching out to one person per week or month, whatever is realistic for you. Track your progress with a list of people you’ve met for informational interviews or advice. Did they have ideas of whom else you should meet? Have you called a headhunter? Spend your 15 minutes reviewing what you’ve accomplished and what’s next on the list. If you’re thinking of a move, have you scheduled a visit to see what it might be like to live there? Is there a way to try out a place or company without actually going there?

A coaching client of mine, Sonia, was the style editor at a major fashion magazine. She had been there for many years and had a great reputation, but the industry was changing rapidly. Revenues were shrinking across publishing, and social media celebrities attracting followers on Twitter and Instagram were upending the business model for fashion magazines. There had already been multiple rounds of layoffs. Sonia knew she needed to leave, but the rest of the industry seemed just as bad. She also knew that if she left voluntarily, she wouldn’t be eligible for a redundancy package. She was the main breadwinner and had two kids in college, so packing up and figuring out what she would do later was not a viable option.

Instead, she decided to explore a partnership her company was involved in with a plus-size clothing designer. She had already been active on the project internally and decided to use it to learn more about the plus-size industry, which was rapidly expanding, to see if it might be a good fit for her.

Sonia was able to explore a new industry and build relationships with a market leader, all without leaving her current role. It gave her clarity about the industry being a place where her skills would be valued. She gained insight into the challenges faced by larger women in finding attractive clothes and found she had a passion for making that easier and more fun. That ultimately made the decision to leave the magazine an easy one and gave her a smooth transition to a new position.

What opportunities can you find to try out new roles or experiences you think you would enjoy? Who can you talk to about what their jobs are like? Dan Gilbert says surrogates are the most reliable ways of determining what will make us happy in the future. Find one or, like Sonia, be your own surrogate.