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When it comes to your personal and professional life, you’ve probably heard the term goal-setting. You’re encouraged to set goals in your job, your finances, your health, even your hobbies. But successful goal-setting requires a very specific skillset.

If you ask people what the magic trick for reaching a goal is, you’ll probably hear motivation. And it’s true, when you’re properly motivated, you can achieve a lot. But motivation can be elusive, particularly when it comes to long-term goals. And not everything you want to accomplish can be tied to your passion or drive. So, how do you find it?

While motivation can hard to find, it doesn’t have to be. You don’t have to tie it to a strong primal urge or require you to only pursue things that spark intense passionate reactions. Instead, you can find motivation in every goal you set by understanding how to set realistic expectations and relate them to your purpose.

So how do you find your purpose?

Effective goal-setting starts with setting up a plan of action that is relevant and specific. They also typically have reasonable timelines so you can measure your progress. And this process starts by asking the right questions. If you don’t ask the right questions while setting goals, you’ll end up failing to achieve them.

But before we get into the right questions, let’s start with the wrong one.

When you think of your goal, what do you picture? If you’re like most people, you probably envision the moment of success. Essentially, you focus on what things will look like after you achieve the goal. The problem is that instead of creating motivation that will endure, you are likely setting yourself up for failure, instead.

Consider the timeline. You may have a realistic timeline set, but the work itself may not be worth your time. Maybe you’re starting at the wrong point, or haven’t taken into account other time consuming obstacles that you will inevitably face. An idealized future is fun to think about, but it isn’t going to sustain you through a difficult struggle.

Thinking of success is important. It helps you keep the bigger picture in mind. But if you think through the process in a realistic and detailed manner, you will be able to assess your strengths, weaknesses, assets, and liabilities to form a solid path forward. And that, is the difference between failure and success.

So, what are the right questions?

1. How much will you regret not completing this goal?

Regret is called a rational emotion and is part of the decision-making process. It is processed in the part of the brain where rationalizing and executive functioning behaviors are regulated. The feeling of success is a positive emotion and imagining it gives you a dopamine high. While this ‘high’ is great for motivation, it fails to alert you of the loopholes, if any, in your plan.

Regret aversion is one of the best cognitive aids to decision-making, precisely because it prompts you to consider possible loopholes in your plan before you make the decision. It forces you to think about the possibility of failure, which prompts your brain to focus on problem-solving any pitfalls that could lead to failing. This will give you a realistic idea of how much work your goal will take and help prepare you for a long-term reality that is less idealized and more within your reach.

If the goal is something that you won’t regret failing, then maybe it should be dropped, or at least given less priority. Maybe success isn’t as clear as you imagined, or worth the time and energy you’re going to have to invest in order to succeed. You might find that picturing failure shows you other goals that are more worthwhile, or help you really identify why you want to pursue it.

2. Can you explain your goal to someone else?

A great way of rationalizing any idea is articulating it. Goals are often vague things and ideas that sound great in your mind, but often leave out important details. Explaining it to someone is a completely different thing.

Ideally, this person will also ask you questions. Be open to their attempts to poke holes in your plan. You might find that your goal is unrealistic given your skills. Anyone can learn how to play the piano, but if your goal is to become the next Beethoven immediately, you need a more realistic goal. Voicing your goal to someone else, along with your plan to achieve it will help you fine-tune and sharpen your goal to be more realistic.

When you keep your goal to yourself, you tend to stay within emotional thinking. But when you have to present your plan to someone else, your rational side kicks in. You might notice right away that you’re missing a step, or are starting at the wrong place. You might realize that you have to start smaller, or be more clear in the action steps you have laid out.

Even if you can’t find someone else to present your plan to, even thinking about how you would explain it will trigger the cause-and-effect questions in your brain. You can use this question to become your own impartial judge, and the more practiced you will become in how to find any faults or weaknesses in your plan. The more questions you can think of, the sharper your goal will become, making success a much higher probability.

If you find yourself struggling with this, you may need to take a step back and reevaluate why you want to set this goal and look at ways to make each step more realistic.

3. Does this goal interfere with your other goals?

Everyone has a multitude of goals in their lives, and you’re no different. Some things may not seem like goals. For example, you may not think getting a raise as a goal, or doing the dishes every night. But these are behaviors you want to either reach or maintain. And those are goals.

Before you start any new goals, you need to sit down and really think about what goals you currently have. If exercising more is your goal but recovering from knee surgery is your current focus, those goals may be in conflict. You’ll have to be very specific in your definition of exercise and make sure it’s within your physical capabilities.

It might be hard for you to launch a new business while also trying to get a promotion at your current job. Both of those goals require you to be focused, work extra hours, and go above and beyond. If you also have a family or other obligations, you may simply be biting off more than you can chew.

You don’t always have to give one up. But you will have to adjust your time commitments and progress expectations. If you’re not careful and don’t plan accordingly, you risk failing at not just one, but both goals.

Before you commit to any new goal, always do a deep dive on your current goals and make sure are being very honest about your existing priorities. Take a realistic approach and adjust your plan of action to one that is specific and achievable.

4. How much you can sacrifice for this goal?

Going after most goals will likely cost you something. Some might demand that you change your lifestyle. You might need to start new habits or stop old ones. And while they all won’t require money, they will demand part of your time, focus, and mental—sometimes physical—energy. Basically, going after your goals will create some amount of pain. And you need to be very honest about how much discomfort you can realistically endure to succeed.

Let’s take the examples from above. If your physical knee pain is elevated when you add exercise to your routine, you may not be willing to do those exercises as frequently as necessary to see progress. The progress may not be worth the added discomfort.

When it comes to weighing your promotion with launching a side business, the main obstacles are going to be time and focus, though financial cost may also play a vital role in this calculation as well. You’re going to have to give every second of your free time to both projects, even on a lengthened timeline. You might have to give up exercise, social time, and even sleep.

This is the point where you might realize that reaching your goal is either going to take too much from you, leading to failure. Or, they may not end up being worth the cost even if you succeed. In order to reach your goal, you need to find a safe middle ground of sacrifices so that the change required doesn’t threaten to end in burnout or jeopardize your existing goals.

The Power Of Why

The point of asking these questions isn’t only to create a solid action plan. They’re also designed to tap into your purpose.

Purpose can be an elusive concept. You might want to lose weight, but what is your underlying purpose? Being healthy is a good start, but wanting to be in good health so you can walk your daughter down the aisle is tapping into a deeper purpose.

The easiest way to discover your purpose is to ask why. Why must you do this? Why is this goal important? Why do I want to achieve this?

You can come up with all kinds of reasons to achieve a goal. The what, where, who, when, and how are all tactical pieces of our goal-setting plan. But the heart of any goal is in the why. Answering this question has to be more than, “because I have to”. There’s all kinds of goals you have to do, but getting a good grade or losing weight is rarely the actual why. It could be that getting a good grade means you have a better chance to getting into the University of your dreams, which means you can get a job you’re passionate about. Losing weight is likely less about the number and more about something deeper like your health or your confidence.

You’ll know when you found the purpose of your goal when you have more than logic attached to it. The purpose, the real why that will drive you to success, will evoke an emotional reaction deep within you. Purpose is meaning, and meaning is heart.


Goal-setting can be an extremely effective tool in building motivation and momentum in the things you want to achieve in life. But it can only be effective if the goal is a right fit for your life. Asking these questions and tapping into your deeper purpose can help you design a roadmap to success in any goal you aim for.

If you want to learn more about setting up goals aimed at success, watch this video:

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