We All Start Somewhere: 5 Steps For Successfully Setting Goals

by Ben Sands

I started setting goals in my early 20s because, well, everyone told me I should.

Sadly, it never seemed to work.

At best, the yearly process created a bunch of new to-dos for me to check off my list: make $250K, read 30 books, take an international trip, suck less at golf, etc. (To be fair, I LOVE crossing sh*t off lists, but still...)

At worst, my approach simply created a set of new distractions, "shiny objects" that created new work, but very little new value in my life. Each year, the cycle repeated itself. And, each year, I questioned why I was wasting the time.

The fact is, I didn't feel like I was making meaningful progress in my life. Simply put, my life wasn't getting better; it was, more or less, staying the same.

The Goal-Setting Mistake We All Make

I was just about to give up on goal-setting entirely when I stumbled upon the work of Dan Gilbert, a wicked smart Harvard professor who helped me understand why I suck at goal-setting... and likely, you do, too.

The problem, as Gilbert discovered, is a simple one: Human beings are terrible at predicting what will make them happy and how long that happiness will last.

As he shared in this interview,

[People] expect positive events to make them much happier than those events actually do, and they expect negative events to make them unhappier than they actually do. In both field and lab studies, we’ve found that winning or losing an election, gaining or losing a romantic partner, getting or not getting a promotion, passing or failing an exam — all have less impact on happiness than people think they will.


So, here's the takeaway for you: Attempting to engineer happiness (or any other outcome) via a traditional goal-setting process is likely a waste of time, energy and money.

That said, if we don't have any kind of plan, we risk an even more undesirable outcome: indifference. If we don't get specific about what want to achieve, the only way we get to a great outcome is by luck.

I prefer to control my destiny. I suspect you do, too.

Because I am both an executive coach and kind of a nerd, I used Gilbert's research and that of others to create a new, better approach to goal-setting -- I call it "regret-free."

"Regret-Free" Goal-Setting: 5 Steps To A Better 2015

"Regret-free" goal-setting is a five-step system that overcomes the inherent flaws of traditional goal-setting and ensures you get what we're all after: lives in which we wake up every day energized and excited about the way we are living.

These are the five specific steps I use — and coach — to help men and women with many personal and professional options create better lives for themselves and their families:

1. Identify What You REALLY Want

Goals, like get a new job, make more money, lose 20 pounds or start a company aren't goals, but strategies. The true goal — what you "really" want — is the feeling you associate with having that new job or losing the weight.

If you want to create goals that matter, start with the feelings you want more of in your life. Some of the most common include security, love, significance, growth, meaning and freedom.

Action: Identify 10 specific feelings you would like to feel more of in 2015. Now, refine that list to a top three.

2. Learn From The Past

So, now that you know what you are after, look back and identify when, where and how you achieved your top three outcomes in the past.

For example, if your goal is security, ask yourself, when in my life did I feel most secure? What was I doing? Who was I with? What was going on? Use your past history to better understand the unique set of circumstances and conditions that make you feel the way you want to feel.

For example, you may discover you felt a great deal of security while working at a particular company or for a particular manager, while in a strong romantic relationship or when your personal finances were more stable.

There is no right or wrong answer, but this step is essential. You must learn from your past in order to more effectively create the outcomes you want in the future.

Action: For each of your top three, make a list of the various ways in which you have created those feelings before in your life.

3. Generate Strategies For Getting What You Want

By looking back, you've already started the process of identifying strategies to make you feel how you want to feel. Now, create an exhaustive list of the various ways you can achieve that outcome.

For example, if what you *really* want is to be healthy, your list might include get more sleep, exercise, eat better, drink less, meditate, read and sign up for the Regret-Free Life newsletter.

If what you *really* want is to be more confident, your list might include find a mentor, take a course, exercise (it works, BTW), create a development plan at work and visit a therapist.

Regardless of the outcome you want, there are various ways you might create more [insert kick-ass feeling here] in your life. You just have to discover them.

Action: For each of your top three, create an exhaustive list of the ways you can create these feelings in your life. If you need help, ask trusted friends or colleagues: "What do you do to feel [insert feeling]? When have you felt most [insert feeling]?"

4. Prioritize By Ease Of Implementation (And Get S.M.A.R.T.)

Now that you have a long list of strategies, identify the low-hanging fruit (i.e. the strategies that will be easy to implement and of high value) and get started.

I describe "easy" as things that a) don't cost any money, b) require a minimal investment of time and c) have been proven effective — in either your life or others.

Action: Identify one strategy for each of your top three and create a "S.M.A.R.T." (Specific, Measurable, Actionable, Relevant, Time-Bound) first step.

For example, if your goal is to be healthy, and getting more sleep is a strategy that appeals to you, identify a specific best practice to implement in a short period of time (e.g. turn off my phone and computer two hours before bed, read a fiction book or no alcohol less than an hour before bed).

Short, achievable deadlines are important for two reasons: 1) They help us to build momentum; if we do something for one week successfully, it's far more likely we'll be able to do it for two weeks. 2) We learn quickly what works and we can course correct.

5. Review And Course Correct

The review process is where it all comes together.

At the end of each week, I make a list of the outcomes I want to create (e.g. more confidence, health, love, etc.). I then go back through the week to identify what worked and what didn't.

Continuing the example above, did the extra sleep help? Do I feel more or less healthy this week compared to last? More often than not, some strategies will work and others won't. The key is to invest in the activities that yield the greatest benefit and stop doing what doesn't work.

Based upon these lessons learned, I then set a new, specific S.M.A.R.T. objective for the next week. Over time, this iterative approach will help you to refine and deepen highly effective habits — what I call "success strategies" — based purely on your own personal preferences.

Action: Put a recurring planner on your calendar for this review session. Thirty minutes every Friday afternoon, or Monday morning, should suffice. Just make sure it happens consistently.

Do you want this year to be better than last? Me, too.

Using this five-step approach to setting goals, you can make it happen. You can set meaningful targets — feelings, not things — and apply simple, iterative approaches to discover strategies that will help you to achieve them.

At the end of the day, goals matter. You define them and then they have the power to define you. Master this goal-setting technique and create a life you love.

Note: If you want to put this plan into action, join me for a high-energy and engaging online workshop: Your Regret-Free Year. During the 60-minute session I will walk you through my step-by-step plan to take your lessons learned and create a plan to make this new year better than last. Click here to register.