Setting Goals: Demystified

It all started while mowing the lawn. When I was growing up in Ohio, I mowed lawns to make money. It was generally a good summer job. I didn’t need to be 16 (the legal working age in Ohio at the time), and mowing lawns was easy to learn, provided decent outdoor exercise, and paid pretty well. 

One drawback of lawn mowing, however, was that it was boring as hell. You push the mower in a line, turn the mower around and walk back. And repeat. The only break from the monotony was emptying the bag of grass and periodically refilling the mower’s gas. 

The savior for all lawn mowing professionals was the Sony Walkman. While my Walkman gobbled AA batteries and one of the headphones always seemed to be broken, listening to tapes provided a much-needed distraction from an otherwise mind-numbing afternoon. 

I stumbled into self-help audio books by accident. For a reason I never understood, but for which I am eternally grateful, the Perrysburg, Ohio, public library had a large selection of “self-help” audio books on cassette tapes. While returning The Beatles’ Abbey Road cassette, I spotted an audiobook entitled, “The Psychology of Achievement,” by Brian Tracy. I checked it out, listened while mowing, and unknowingly began a lifelong journey into my own self-improvement. My Ohio summers would take me through classic audio books by Zig Ziglar, Dale Carnegie, Anthony Robbins, Napoleon Hill, Earl Nightingale, and many others. I walked up and back in the hot sun brainwashing myself with content. 

In the 35 years since my lawn mowing days, I have continued my fascination with and study of self improvement. The foundation of most self improvement starts with setting goals. So I thought I would summarize 35 years into one page and three bullet points. You’re welcome.

1. Ask the right questions.

2. Schedule time on your calendar to answer these questions.

3. Write your goals daily.

Ask the right questions

It is so simple, but your conscious mind, your subconscious mind, and even your body and heart will line up to answer the questions you ask yourself. Many of us either don’t ask questions or we ask the wrong questions. We ask, “Why me?” or “How could this person do that?” or “Why am I not as good as this person?” or “You idiot, why did you do that?” 

“I have achieved my largest goals— the goals I write down every day for a year or longer—nearly 100% of the time.”

Here is my favorite question of all time. “If a magical genie came out of a bottle and granted me a wish—for my life or career—and I knew with 100% certainty that wish would come true, what would I wish for?” Explore this exercise yourself here. What would I really want to do?  What if the genie granted me a wish for my body, for my friendships, for my relationship with my partner or kids? In other words, what is my dream state? 

A few other examples of great questions, “If I had to achieve my five-year goals in six months, how would I do it?” or “What can I and only I do which will make the biggest impact on X?” Refer to my list of expansive questions organized by category. 

Asking the right questions will give you a sense of your North Star. What matters? What will give my life meaning? What general direction should I head in my business, career, relationships, or spiritual life? Which habits do I want to develop?

Schedule time to answer the questions

Most people wake up today and do what they did yesterday. Then tomorrow they do what they did today. And they string those days together and call that a life. By taking control of our calendar and scheduling regular blocks of time to ask and answer expansive questions, we create a North Star for our lives. Here are my own examples:

• One or two annual weekends with my former roommate where we rent a cabin, go on walks, and map our lives. 

• One three-day offsite with our whole firm at Alpine to set our vision, values, five-year, and one-year goals.

• Quarterly full days with the Alpine partners to align on key decisions, changes, and quarterly priorities.

• Weekly three-hour sessions with my partners to discuss key weekly goals, investments, and priorities.

• Weekly or bi-weekly calls with my executive coach to talk about difficult situations and to hold me accountable to my important priorities and decisions.

• Daily meditating, journaling, and goal setting.

That may seem like a lot of time planning, but as Abraham Lincoln once said, “Give me six hours to chop down a tree and I will spend the first four sharpening the axe.” Even with all the scheduled “sharpening” I listed above, my ratio of chopping to sharpening is greater than 10 to 1— I’m still falling well short of Lincoln’s prescribed ratios.

With the exception of the daily meditating, journaling, and goal setting, all of my “sharpening” involves other people— my partners, my former roommate, or my executive coach. Studies show that we activate different parts of our brain when we talk to other people, and I find that I am most creative and expansive when talking with others. Sharing my goal setting with others is less lonely and makes me more accountable to the schedule and the goals. 

Questions like, “What would be a meaningful life?” or “What is my genie-inspired career aspiration?” or “What is my ideal relationship with my partner?” are challenging. The answers may not come easily. At Alpine, we dedicate many, many hours over the course of a full year to answering questions about how we hit our target returns, how we keep A players, and generally how we thrive in the current environment. The process can get messy and can feel unsatisfying if we don’t find answers right away. 

Keep asking the questions, keep discussing with others, and keep working at it. The answers will come. Your North Star may start out as something like, “I know I want to work with amazing people in my career,” and that’s a good place to start. Over time, you will get more and more specific and your North Star will come into view. 

Create a daily habit of writing out your goals 

Yes, daily. The single most important thing I learned from all the hours I spent studying self-improvement was to write my goals every day. I spend about five minutes writing out four things every day: 

1. What is my North Star, my genie goal, my five-year goal, or my 10-year plan? I list three of these goals. This is designed to capture the general direction I want for my life.

2. If I could only achieve three things this year, what would they be? 

3. If I could only achieve three things today, what would they be? 

4. What are my three most important interactions today and how will I show up in each? 
   

The first two things are always the same, and that's the point. We're trying to get our subconscious mind working for us in order to program our goals into our minds. We are “brainwashing” our subconscious mind daily with our purpose, mission, and direction. We're programming our minds to work for us and to work toward our highest vision and purpose. 

From a lifetime of setting and achieving goals, I’ve noticed two surprising things. First, I have achieved my largest goals— the goals I write down every day for a year or longer—nearly 100% of the time. I haven’t always achieved them exactly as I wrote them or in the time frame I set for them, but nearly all of the goals I’ve dreamed up over my life have yielded to the process of daily intention and action. 

Second, the payoff for a life of setting big, exciting goals has been more than the achievement of the goals themselves. My identity has changed over time. I have gained tremendous confidence in my abilities and I have come to think of the world around me not as static, but as a place I can influence and impact. 

I want to leave you with two questions:

1. If you had a magical genie come out of a bottle and grant you a wish, what would you wish for? Be careful what you choose—with this process, it will likely be yours!

2. Are you willing to dedicate five minutes per day and several hours per quarter to sharpening your axe to bring this genie to life? 

Feeling inspired? Looking for a summer read? Check out my bookshelf to see a few of my favorite titles and send me your own inspiring books about self improvement. I would love to add more authors to my collection!