The Truth About Success: How to Know If Success Will Make You Happy

You have checked every box, climbed every ladder, and earned the respect of your peers. You make great money and, on paper, you are absolutely killing it. Yet, when you close your eyes at night, there is a nagging feeling that something is off. Deep down, you are unhappy with your success. Why does it feel that way, you?

The usual suspects are stress, a lack of time, or just being “too busy.” But let me tell you something real – those are just symptoms. They aren’t the disease. The root cause of that emptiness is actually how you define success in the first place.

Before we dive in, I want to check in with you, lovely. Does this resonate? If you have ever felt a twinge of guilt for not being over-the-moon happy despite having “it all,” share a heart in the comments below. You are definitely not alone in this feeling.

Your Definition of Success Matters

Tell me how you define success for yourself, you, and I will tell you whether you will end up happy 3, 5, or even 10 years from now. It doesnt matter how shiny your life looks to the outside world. Your internal definition of success is the roadmap that guides every single decision you make.

It heavily influences:

  • the goals you set for yourself;
  • the career path or projects you choose to chase;
  • what you work hardest for; and
  • the promotions you say “yes” to.

Think about it for a second. How you define success guides every big career move you make. It affects your personal life just as much. If your definition of success isnt aligned with your individual desires, needs, and values, you are following a roadmap that wasn’t printed for you. This incorrect map might take you to the top of the mountain, but you’ll get there feeling cold and empty, yearning for something meaningful.

The Problem with Most Definitions of Success

A Definition That’s Way Too Narrow

Ladies, success isn’t just about career achievements and the zeros in your bank account. Yet, for so many of us, those are the only two metrics we use. That way of looking at life is just way too narrow.

Real success is about feeling content and satisfied with who you are. It is about being at peace with your decisions when you lay your head down at night. You are a complex, beautiful, multi-dimensional being. While we all want to crush it in our careers, there is so much more to life. Your definition needs to include what actually lights you up inside.

We Want to Hear From You!

I’m curious – what is one thing outside of work that brings you pure joy? Is it painting, hiking, or maybe just a quiet coffee in the morning? Share your joy in the comments below – let’s inspire each other!

Values and Standards That Aren’t Yours

Most of the time, our idea of success is a messy mash-up of:

  • what society tells us is successful;
  • what our family expects of us; and
  • a tiny bit of what we actually want.

There is no place in your life for a definition that isn’t based on what you truly desire. All those expectations from other people? We call those “shoulds”. And honestly you, they need to go.

Including “shoulds” in your life will put you in a repetitive cycle that crowds out the things that matter most. You are human, which means you want to be loved and accepted. When you get praised for achieving those “should-based” goals, it feels good for a hot minute. But before you know it, you are far down a path that feels exhausting and unfulfilling.

Clues That Your Success Definition Isn’t Truly Yours

This might sound crazy, but many people dont realize their life goals are based on what others want. We are conditioned to care about what people think. It is especially hard to see when you are living a fast-paced lifestyle. So, how can you know before it’s too late?

Be on the lookout for these warning signs, lovely:

  • Something feels missing or you crave “more” (but you aren’t sure what that is);
  • You hit your goals, but the satisfaction is fleeting or non-existent;
  • Your work often feels laborious, tedious, or just plain boring.

If you are nodding your head right now, it is a likely indication that your definition of success needs a makeover. It is time to redefine it your way.

How to Be Successfully Happy by Defining Success Your Way

So, how do we fix this? How can you ensure you will be happy with your achievements? The answer is simple, you: redefine what success means to you on your own terms. Do it from the inside-out.

This means considering:

  • What you need to feel whole financially, physically, emotionally, and spiritually; and
  • Your core values (the stuff that gives you purpose).

Step #1: Prioritize Self-Care (For Real)

If you want to define success on your terms, you must prioritize self-care. I know, I know. When I mention self-care to high-achieving professionals, I get a lot of eye-rolls. But listen to me – self-care isnt just bubble baths and escaping reality.

The purpose of self-care is to ensure your physical, spiritual, and mental well-being. There is nothing optional or selfish about that. You need clarity to know what you value, and you cant get clarity when you’re stressed out.

Try this: Set aside just 10 minutes a day to sit in stillness. Take slow, deep breaths. It’s a form of meditation. Pay attention to what comes up. Maybe even journal a bit. This simple practice helps your subconscious thoughts bubble to the surface, giving you the awareness you need to know what you really want.

Step #2: Reconnect with Your Core Personal Values

Your values shape who you are. When you align your life with your values, you feel fulfilled. When you don’t? You feel like something is wrong. I had a client who felt unmotivated in a job she used to love. Turns out, one of her core values was “community,” and she wasn’t getting that anymore. Once we fixed that, she felt alive again.

Ask yourself these questions to find your values:

  1. When have you felt most angry or disappointed with yourself? What rule or standard were you ignoring that is important to you?
  2. At the end of your life, what do you want people to say about you? Look for the common themes.

Let’s Support Each Other

Have you ever achieved a massive goal only to feel… nothing? Share your experience in the comments below – your story might be exactly what another woman needs to hear today.

Step #3: Create Your Own Definition of Success

Once you are taking care of yourself and you know your values, you are ready to create your own definition. Create it from the inside-out. Make sure it encompasses you as a whole person and leaves out the “shoulds”.

As you decide what success means to you, run it through this test:

  • Ask how it relates to your values – what is meaningful about it?
  • Challenge your answers. Ask “why” is that meaningful?
  • Keep asking why until you are satisfied it’s important to you, or you realize it is just an expectation from someone else.

Once you go through this, you will have a new roadmap. One designed specifically for you, you. Use it to make better decisions so you can finally feel fulfilled, happy, and at peace.

Join the Conversation!

If this article sparked a realization for you, share it with a friend who might need a reminder that her happiness matters more than her resume. And don’t forget to drop your thoughts below – I read every single one!

 

Frequently Asked Questions

Why do I feel unfulfilled even though I am successful?

Often, high-achievers feel unfulfilled because their definition of success is based on external validation, societal standards, or family expectations ("shoulds") rather than their own core values and desires. When your roadmap isn't aligned with your true self, the destination feels empty.

How do I find my personal core values?

To find your core values, reflect on moments when you felt most proud or, conversely, most angry or disappointed in yourself. These emotions usually point to a value that was either honored or violated. Also, ask yourself what you want to be remembered for at the end of your life.

Is self-care really necessary for career success?

Absolutely! Self-care isn't just an indulgence; it is essential for mental clarity and emotional resilience. Without it, you cannot clearly hear your own intuition or define what success truly looks like for you, leading to burnout and poor decision-making.


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about the author

Sage Montgomery

Sage Montgomery is a fulfillment strategist and lifestyle designer who helps women create lives aligned with their deepest values. After achieving everything society told her would make her happy-only to feel empty inside-Sage realized that success without fulfillment is the ultimate failure. Now she guides women in defining success on their own terms, pursuing passions that matter, and building lives rich with meaning and joy. Her approach is thoughtful, strategic, and deeply personal, recognizing that each woman's path to purpose is uniquely her own.

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