11 Questions to ask yourself to set better goals (that you’ll actually achieve)

You're finally relaxing at the end of the day. You’ve closed your laptop and put your kids to bed. Now, you’re decompressing with “just a quick scroll” through Instagram. An hour later, you’re thinking about all those things you “should” be doing. “I should really workout more, or travel more, or earn more.” And you quickly set a goal to do just that.

Or maybe, New Year’s is coming up and you’re thinking about those resolutions from last year that you didn’t keep and decide to double down on them. This will be the year, right?


These kinds of spontaneous goals almost never work out. But that doesn’t mean all goals are hard to achieve. It just means that you need to be more intentional in your goal setting. We’ve come up with a list of questions as you decide on and refine goals. These 11 goal-setting questions will help you lay out goals that you’re not only more likely to achieve, but more likely to be proud of when you do.

1. Why do I want to achieve this goal?

First thing first: You need to make sure you’re choosing the right goal.

“When you choose the wrong goal entirely, it might feel like pushing a boulder up a hill without any traction whatsoever,” says Jennifer Fink, owner of Fink Development.  “Even if you do reach the goal you might wind up feeling just as unsatisfied or unfulfilled as when you started.” 

Instead of picking a goal based on what you think you “should” be doing, you can build goals in alignment with who you are, what you care about, and what will create the biggest impact. Look inward and think about your core values, strengths, and interests. Think about how your possible goal ties into these aspects of yourself.

If it doesn’t, maybe you need to rethink things. When goals aren’t based on the values and interests you truly care about, your motivation won’t be as high, which is one of the critical components for consistently working toward any milestone, Fink says. 

2. What problem am I solving or desire am I fulfilling with this goal? What benefits will I get from achieving this goal?

A strong, achievable goal needs to be intentional. You likely have a number of areas you truly care about. Within these areas, consider what your biggest problems are or where you feel like you’re lacking, and choose a goal that will improve it. 

So maybe you’ve decided one of your core values is community, but you’ve been feeling a bit disconnected or lonely. Upon exploring that, you might realize that you haven’t been spending enough time cultivating relationships or giving back to a cause you care about this year. The benefit of both of these activities would be increased connection with a community, so either one of those can be part of your goal.

3. Will this goal create the greatest positive impact for me in my life and/or career right now? If not, is there a different goal I should choose?

Most people have more than one area of their life where they want to move forward, so you’re likely to come up with a number of intentional, value-based goals that you could work on. But start with the one that will have the biggest tangible improvement on your life as it is now.

Perhaps, physical health is something you care about, and lately, you’ve been feeling tired all the time. One of your lifetime goals has always been to run a marathon, but starting an intense training regimen might not be the most useful goal right now if you know you haven’t been getting enough sleep. Or maybe you’ve been struggling for money for a while and you know a higher paying job would not only improve your career but also decrease the stress that’s been keeping you from making progress in other areas so you might choose to prioritize that.


4. Is my goal specific enough?

It’s hard to measure success when you don’t know what success looks like. So make sure you’re specific about your goals. “Eating healthier” is hard to gauge. But adding an extra serving of fruit or vegetables a day is much more concrete.

On the other end, a vague goal can also make it difficult to get started. If your entire goal is to get better at public speaking, how do you do that? A more specific goal like “take a public speaking class” or “join an improv group” has a clearer path forward. 

Goals that are not specific enough tend to fail because “they often trigger a lot of mental and behavioral resistance that is difficult to overcome,” Fink says. So make things easy on yourself from the start.

5. What deadline am I setting to achieve this goal?

You’ll also want to add a time frame to your goal. Think about it. When your boss says, “At some point can you look over this old spreadsheet and make a more efficient one?” that’s probably not going anywhere near the top of your to-do list—if it makes it on there at all. But if your boss asks for a new spreadsheet by the end of the month, you can more easily see where it fits in among your other duties.

6. Is my goal realistic?

An unrealistic goal is often an under-researched goal. “Not understanding if the goal is realistic can lead to unnecessary stress and disappointment, especially when the goal isn't met,” says Lisa Thomson, a coach at Fink Development. “Taking the time to understand what is realistic upfront can help keep motivation throughout.”

For example, Thomson often has clients tell her that they want a new job in a certain number of months or by a certain date, but when asked they’ll admit they didn’t research the current job market or common hiring timelines for their industry. Instead, their goal is coming from a preference.

So before you finalize your goal, fill in any gaps for yourself. Talk to people who have achieved what you want to achieve. Research what your goal actually entails. And of course, evaluate where your life and current responsibilities are. For example, wanting to finally write that book over the next year may be doable in normal circumstances, but not if your partner is pregnant with your first child or you know your current job leaves you too drained to write more than once a week.

Make sure your goal isn’t just too “big” either. This goes back to specificity, but a longer term, but more difficult goal may be more achievable if it’s divided into smaller milestones. “Psychologically we feel upset when we don't achieve the goal and we lose motivation,” Thomson says, “If we intentionally set small, achievable goals, we receive the positive dopamine response to achieving it — making us more likely to attain larger goals over time. “

And setting unrealistic goals doesn’t just increase your odds of failure, it makes it harder to get started. According to Fink, if you set a goal without knowing how possible it is, what steps you need to take, and what habits you need to develop, “It will be very difficult to know how to move forward without feeling completely overwhelmed or confused or defeated by not seeing enough progress quickly enough.”

The most realistic approach, Fink says, is to choose a goal based on a foundation of reality and then push it a little further to set a stretch goal that’s ambitious, but still achievable. For example, if your goal is to read more books because you value literature (and want to spend less time watching TV) but you only read 3 books last year, setting a goal to read 20 books may be unrealistic, but something like 6 or even 10 could be achievable.

 Or if you already cook yourself dinner two nights a week, maybe set a goal of three or four nights a week rather than jumping to never getting takeout or delivery again.

7. What are the steps I expect to follow to achieve this goal?

If you’re old enough to remember a time before GPS on every phone, you likely remember printing out driving directions from MapQuest. You also likely remember turning around and driving home to get the directions after you forgot them in the printer. Because how are you going to get somewhere you’ve never been before if you don’t know the steps along the way?

Knowing the steps toward your goal before you begin will keep you on track and keep you from giving up when things feel too “big.” Because you don’t need to focus on all the steps at once, you just need to focus on the next step.

If you don’t know what the steps are, again it’s time to do your research. You may be able to find resources online or get advice from someone you know, or figuring out the steps may become your first step or goal itself. After all, before MapQuest, there were just maps. 

8. How will I create consistent habits to achieve this goal?

What actions and tasks do you need to work into your routine in order to hit your goal on time? If your goal is connected to fostering relationships with others, you might need to check in with these people more often or make time to see them, for example. If you want to build a skill, you’ll need to learn the skill and practice it. If you want to complete a project, you’ll have to spend time actually working on the project.

The habits come in when you work these tasks and actions into your life as it exists now. So think about when and how this goal will fit in. Maybe you’re setting aside the same block of time every day or week to focus on your goal. Maybe you’ll be most successful if you set a goal for the number of times you engage in your habit, or connect it to a current activity. For example, maybe your new meditation habit fits in nicely after you brush your teeth in the morning or at night, or you can read about the skill you’re building on your train ride home.

9. Are there any obstacles or blockers I see toward achieving this goal?

You’re way more likely to push through setbacks if you already have a plan in place. So try to anticipate what might get in the way of your goals. Maybe you know your biggest obstacle will be free time or holding yourself accountable. Or you may have responsibilities that you need to prioritize like kids, an aging relative, or an unpredictable work schedule. Perhaps part of your goal is expensive, and money is tight. Or you’ll need to travel, but don’t have reliable transportation. 

Go through the thinks that are likely to trip you up and come up with possible solutions. They could be as simple as setting your phone to “Do Not Disturb” for a certain time period. Or maybe you’ll need to ask your manager for a set time off each week for an appointment.

Unfortunately, you may find that some of the obstacles may be difficult or impossible to overcome right now. That’s OK. It’s better to find out now so that you can adjust your goal accordingly rather than when you’ve already put in a lot of time and effort.

10. Who could I recruit to support me in achieving this goal?

Help from others can help you achieve your goals in a number of ways. For example, people you know may be able to provide guidance or advice, a dedicated coach or teacher can share knowledge and give you feedback, or someone in your network might be able to connect you with someone else who can provide more help.

Sometimes the help you need isn’t directly related to your goal. For example, maybe you need your partner to entertain the kids while you’re taking a class, or handle cooking dinner on Wednesday nights for the next few months. 

Then there are the people who you can turn to as “external accountability partners,” Thomson says. “That could be a boss, mentor, colleague, coach. Especially when it comes to career advancement or career pivoting — setting goals and sharing them will increase the likelihood that you will follow through.” Depending on what’s best for you, this could mean sharing major milestones or even having a friend text you to make sure you’re focused on your goal during the time you’ve set aside for it.

11. Where have I gotten stuck in achieving this goal in the past?

We’ve all set goals that we haven’t achieved in the past. It’s a near-universal experience. But that’s nothing to be ashamed of. Instead, reflect on your past shortcomings to prepare for your next attempt.

“Goal setting is a continuous journey of growth and development,” Fink says. “A lot of people believe (or want to believe) that they can set a goal and have a straight (easy) line from where they are to where they are trying to go. But, the reality is that it just doesn’t work that way. Instead, it’s a twisty windy path of learning, failing, trying, iterating, and refining where you’re trying to go and adjusting your behaviors, actions, and mindset to achieve it.” 

So think about what’s gone wrong for you in the past and adjust your goal—or your plan to achieve it—accordingly.

Getting to your end destination, especially when you’re aiming for big and ambiguous goals, is challenging, Fink says, “And sometimes starting with the expectation that what they are trying to do is hard, helps you find comfort along the journey.”

When we work with clients on goal setting we help them get crystal clear on their most aligned, authentic and intentional goals from the get-go. Then we teach them new tools and strategies to combat the inevitable mindset and everyday life obstacles that will get in their way, and help them design a realistic roadmap to chart their path forward. 

Want to learn how? Check out our Vision and GoalSetting Workshop here

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1) Join Our Job Search Accelerator Membership. Our structured step-by-step process to clarify, attract, and land your ideal opportunities.

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