You’ve worked hard to excel in a career you’re crazy passionate about. You live in a city you used to dream of calling your own. You have several amazing people you feel lucky to call friends. You’ve even traveled the world.

At first glance, it may seem like you have the perfect life.

But, if you’re like a lot of the badass high-achievers I work with, you still go to bed every night thinking, “I have everything I could ever want…so why am I so totally unhappy? And what can do I about it?”

Why You’re Not Happy with Your Life

Sometimes, this unhappiness emerges with time. Things that used to make you happy – closing a huuuuge deal with an important client, going on Instagram-worthy vacations, you name it – simply don’t fulfill you anymore. Or instead of being excited to wake up for work every morning, you start thinking, “Here we go again. Well…at least there’s only five more days until the weekend.”

In fact, I like to call this change the “mid-life malaise” because it seems to strike people once they’ve settled down into their lives and careers.

A lot of times, though, this unhappiness is also a natural side effect of being an overachiever. Here’s why.

1. For high achievers, one “success” is never enough.

Think about the moment you cross the final “t” on an important business proposal you’ve been working on for months. How do you think you’ll react: by taking the rest of the afternoon off to celebrate…or by planning which task you’ll conquer next? If you’re a high achiever, you’ll probably do the latter. After all, high achievers are constantly trying to achieve more and grow more and be better, so there’s always another benchmark to meet.

But you want to know the cold, hard truth? A lot of times, people don’t even know why they’re trying to be more rich or more famous or more talented, or more professional or whatever. Usually, they just think they should because “more is always better.” But growth isn’t always a good thing!

Like I tell my clients, “Growth for the sake of growth is the mindset and attitude of a cancer cell.” Sometimes, contentment or peace or rest is better than growth could ever be. But because many overachievers don’t realize this, they keep moving their standard of success higher and higher…

…which means they can’t ever fully appreciate whatever successes they do achieve. If this sounds familiar, you already know just how crappy this cycle can make you feel. You set a goal. You reach it! But instead of feeling fulfilled and happy, you’re sad. Disappointed. Exhausted, even. Because you know your battle for the next “success” has already begun.

And none of those feelings are good ingredients for the happy, fulfilled life I know you want to have.

2. High achievers eat, breathe and live work.

Now, I’m going to ask you another question and I want you to pretend you’re having a one-on-one with Oprah and answer 100% honestly: What have you given up to get where you are now in your career?

Finding a partner? Getting in touch with your inner self? Building a rich social life? Bonding with your family?

The truth is, establishing a successful career is hard. Even more importantly, it’s time-consuming. So when you decide to buckle down and become the next Tory Burch by age 28, you inevitably cut back on the amount of time and energy you can dedicate to other areas of your life.

And there can be a huge problem with that…eventually. Not at first, of course. In the beginning, you feel proud of all that you’ve accomplished. Earning a new promotion or making a new business contact makes you feel powerful and capable and maybe even a little high! But every job has something a little wrong with it – whether it’s as small as a cramped office or as big as a Devil-in-Prada-esque boss. And no job can fulfill every single need that you have as a human. It doesn’t matter if your job is totally aligned with your life’s “purpose.” You still need family, health, friends, fun, creativity, relaxation and so many other things to have a fulfilling life.

And once you realize that and how you’ve let some parts of your life wither to single-handedly prioritize your career, a wave of emotions will hit you.

Regret for the time you spent typing out reports instead of playing soccer with your niece. Loneliness now that you’ve built an empire but have no one to share it with. Sadness for all the parts of your life you now see as cold and empty. And worst of all, fear that it’s too late for you to change.

And I think it’s safe to say that even the most fantabulous job can’t balance out cruddy feelings like those.

3. High achievers are expected to be strong and put-together. All. The. Time.

If you look up the definition of “overachiever,” it’s something like “to perform in a way that exceeds expectations, especially those of others.” So it’s no surprise that we expect overachievers to be unemotional and composed. Able to handle any problem. On top of everythang.

And these kind of expectations are what causes countless CEOs, business owners or just leaders of their own family to walk into my office saying, “But I can’t be upset! Or confused. Or dissatisfied. Or uncertain. I just can’t!”

Which is what causes the next big can of worms. Perhaps my most popular and important teaching is that rejecting or pushing down your real feelings just makes those feelings of fear or inadequacy or sadness a million times worse. Combined with the other factors of dissatisfaction that I’ve talked about in this post, it’s no wonder that you’re feeling sad or unhappy about your life right now! You’ve pushed these feelings to the side for so long, they’re finally bubbling out…

How to Feel Happy Again: What You Can Do

Any of those three points hit a little too close to home? If you’re anything like me, your answer is a big, “Hell yes!” So now that you know a little about WHY you might be unhappy with your life, what can you do to feel happy again?

I have a couple suggestions….as you might have guessed 🙂

1. Pause and reflect.

I get it. Life is busy. Especially if you have a demanding job and are trying to have an active social and personal life, you’re probably running from one errand to the next all day long. But the first step to feeling happier about your life is actually stopping.

What do I mean? Just pause. Recognize that you’re having a difficult time. Recognize that these sad feelings suck and are hard to deal with. Offer yourself compassion…and consider the following scenario:

You’re enjoying a mint julep in your favorite local bar when you start chatting with the stranger sitting next to you. And suddenly, that person is spilling out their whoooole life story, saying, “I’ve kicked ass. I’ve worked like a monster my whole life, working as hard as possible. All. The. Time. I do my best to make my team happy, my family happy…but now I’m not feeling happy or fulfilled and I don’t know what to do about it!”

How would you react? Would you scream at them to “suck it up” and tell them that their feelings are “wrong”? Or would you remind them that they had good intentions, and they shouldn’t blame themselves for how they’re feeling now?

Let’s be honest – you’d do the latter! And you should show yourself the same kindness and care.

2. Find out what’s missing from your big picture.

In a perfect world, we’d all be born knowing exactly how much time to spend on different parts of our lives to make us completely happy. But neither the world nor we are perfect…so sometimes we need to reevaluate and reset our schedules!

“But Caitlin,” you’re probably thinking. “How do I figure out something that’s missing in the first place?”

Start by asking yourself these kinds of questions: “If you had one hundred million dollars in the bank right now, who would you choose to be and what would you choose to be doing? How would you spend your time, and what would you be putting out in the world? What work would you be doing – who with? Who would you not be working with? What would you be doing for yourself? Where would you live? Who with?”

Keep asking yourself, “What else? What else?” until you have a clear picture of the life and identity you actually want. And don’t just visualize what you want out of your job. Consider your family. Your body. Your friends. Your recreational activities. Your spirituality. Anything and everything related to you and your life and happiness.

And if you keep asking and asking, but still can’t nail down exactly what you really want, check out my Personal Happiness Formula workbook. In it, I take you through the exact, step-by-step process I use with clients to create abundant clarity and joy in their lives. This way, you can define happiness in your own terms and learn what concrete, practical steps you can take to live a happier life. Learn more by clicking here.

Once you know what happiness looks like to you, choose one or two areas in which your “perfect life” seems out of alignment with your real life. For instance, maybe you notice that you want to travel…but you never take time off of work. Then, take concrete action to make your real life look a little more like your dream life. Like by saying “no” to overtime and booking your dream vacay to Hawaii instead!

3. Open up to people.

I know. Opening up about your struggles and vulnerabilities is super scary, especially if you always want to be seen as that “strong,” “has-it-all-together” amazing person. But reaching out to people that you trust and who may seem to have more balanced or more fulfilled lives can be a HUGE step in the right direction toward feeling happy again.

Telling others about the struggles you’re having right now will finally let you release all of that tension and fear and hurt you’ve been holding inside. Plus, asking for support lets you be vulnerable and cared for in a way that you probably haven’t let yourself be in a very long time but really need. It reminds you that you don’t have to be perfect or strong or “the helper” to be loved, worthy and acceptable. And that reminder can help you break free of the overachieving mindset that is contributing to your unhappiness in the first place.

What I Hope You Know About Feeling Unhappy With Your Life

One of the biggest takeaways I hope you get from this post is that you are allowed to be unhappy even if you “have everything.” Even if you’ve achieved “everything you’ve ever wanted.” Even if you were happy with your life a few years, months or even days ago!

In fact, like I’ve discussed in this whole post, having the never-ending drive to chase what you want in life and get it can actually be part of the reason why you’re not happy. So know that you aren’t “broken” or “wrong” for feeling this way. But also know that you can change…both your life and how you feel about it.

After all, you’ve already accomplished a TON in life, and you’ve shown you can kick plenty of ass! So I know that you are totally capable of finding your true happiness again. You just need to change your ultimate goal from achievement and perfection to peace and true fulfillment!


What’s one way you’re going to help your “real life” better align with your “dream life”? Tell me in the comments!