Not Sure Your New Dreams Will Make You Happy? Ask Madeleine

August 2, 2025 Madeleine Homan Blanchard

A woman standing on a balcony, looking thoughtfully into the distance, with colorful hot air balloons floating in the sky. Text overlay asks, 'Not Sure Your New Dreams Will Make You Happy?'

Dear Madeleine,

I read Feeling Trapped with interest and it scared me. I have had several jobs in retail and have been promoted to manager in each one, only to become disillusioned with the owners.

I also just ended my marriage and moved to a new city for a fresh start.

My dream is to be an entrepreneur. I am ready to set some big goals for myself, get super focused, and work hard. I have a great idea and even a potential investor lined up.

Here is my question: How do I know that I am setting the right goals? How can I ensure that achieving my goals will make me happy? The idea of busting my butt for twenty years only to end up disappointed is terrifying. If that is going to happen, why bother? Any insight you can share would be helpful.

Anxious Goal Setter

________________________________________________________________________________________

Dear Anxious Goal Setter,

You aren’t going to like this. Ready?

Research shows that humans are remarkably bad at predicting what will make them happy. There is an entire field of study devoted to what is called affective forecasting, which are the predictions we make about our future emotional states. We tend to significantly overestimate both the intensity and duration of future emotions, a phenomenon known as impact bias or durability bias. You can find a lot more detail about that here. Even Feeling Trapped—the writer of the letter you mention—is probably already (a month or so later) feeling very different than he might have anticipated.

You have probably heard the saying “We plan and God laughs.” I used to think that was meant for me because things never go the way I think they should, but it appears to be true for almost all of us. There is simply so much in life that is out of our hands.

There are some things you can do, though. Here are some principles to keep in mind to avoid having terrible regrets.

    • Focus on what matters most

Make sure the goals you set are aligned with what matters most to you—not to your parents, significant other, or community. Stay focused on the end you have in mind. Don’t invest a lot of time and effort in the means to that end. In other words, if you want to be an entrepreneur so that you can be your own boss and realize your vision, go for it. If you want to be an entrepreneur to make a ton of money, forget it.

Not that you can’t get rich being an entrepreneur (although it is statistically unlikely), but you’ll be happier if money is the cherry on top of the sundae of something you want to accomplish. If you want to make a ton of money, do something that will definitely make you money.

The way to know what you really want is to ask yourself: What will I have when I achieve the goal? And what will I have when I have that? And what will it mean when I have that? This classic coaching question, asked about seven times, will help you clarify what you really want. Go for that, whatever it is.

    • Stay mindful and agile

Values do change—and what matters most right now may matter less in the future. Find a way to check in with yourself on a regular basis and ask: Am I still engaged? Am I still having fun? Is this resulting in what I wanted?

You don’t need to pivot or bail at the first sign that you may be on the wrong track. The more actions we take to move toward our goals, the more feedback we get from the universe. Sometimes the message is unmistakably clear, like “Keep going, you’re on the right track” or “Stop and try something else.” But it can be hard to know for sure.

My rule of thumb is that you have to really pay attention when you get three instances of the same message. You can’t let yourself become so mono-focused on achieving your goal that you ignore what is right in front of your face. Staying alert to reality can also help you recognize subtle opportunities.

    • Analyze your patterns

There is a chance that you have a pattern of having high expectations and then being disappointed. If that is true, you can find clarity by working with a therapist who can help you pinpoint the pattern and suggest ways to interrupt it.

    • Create daily structures that feed you

There is the big picture, and then there is the minutia of everyday life. Make sure, no matter what goal you set or how hard you work, that you build things into your life that sustain you—time with loved ones, exercise, a hobby, a pet. These are the small things that will ensure you enjoy your life no matter what happens with your goals.

    • Recognize what you can and can’t control

The Serenity Prayer, known to people in recovery but relevant to all, goes like this: “God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.” It doesn’t matter if you believe in God or not, the general idea is useful.

Finally, the research on happiness shows that happiness can be a choice. Genetics, environment, and life experience certainly contribute to one’s ability to create a happy life, but we all know people who have everything there is to have and are still miserable.

According to Barbara Fredrickson’s broaden-and-build theory, positive emotions broaden perspectives, which in turn build lasting psychological resources such as resilience, creativity, and social bonds. Ever-increasing happiness isn’t just about momentary pleasure; it’s about choosing mindsets and habits that enable long-term personal growth.

All this to say, it might be a good idea for you to study happiness and develop habits that will ensure you enjoy the day to day and end up being thoroughly satisfied with your life, no matter what other goals you set. Positivity by Barbara Fredrickson, The How of Happiness by Sonja Lyubomirsky, and both Authentic Happiness and Flourish by Martin Seligman are all oldies but goodies that will really help you right now.

You can’t let your anxiety keep you from taking action. The universe honors action. Taking action will generate feedback. Feedback is information you can use to decide on your next actions. Doing nothing is as much a choice as doing something, but it isn’t a choice that will generate energy or provide information.

So go ahead and be anxious, but don’t let it stop you from taking the next step. Take care of yourself, surround yourself with good people who love you, have a little fun, and work hard. Will you make some mistakes? Sure. Will you learn from them? Undoubtedly. In twenty years, a wise and happy you will look back and be glad you took the plunge.

Love, Madeleine

About Madeleine

A professional headshot of a woman with short blonde hair, smiling, wearing earrings against a blurred neutral background.

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services as well as a key facilitator of Blanchard’s Leadership Coach Certification courseMadeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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