Breakthroughs, Empowerment, Following Your Dreams The Top 10 Life Mistakes That Make Us Struggle Most Written by: Kathy Caprino


Five years ago, I wrote a post called “My 52 Mistakes” about the worst missteps I’d taken in my life, and what I’d learned from them.  At that time, I was compelled to share these 52 learnings, because after living through the pain and struggle that came from these “mistakes” and trying to undo the havoc they wreaked on my life, I wanted to help others avoid them at all costs.  People wrote me from all over the world about how these mistakes resonated with them, and mirrored their own life experiences.

Truth be told, I don’t really believe in the notion of “mistakes” because I’ve seen that everything that happens can be for our highest good, if we learn the right lessons and integrate them for our growth. That said, there are, without doubt, error-ridden directions we follow that lead to disaster, pain, sadness, and loss.  And if we don’t understand the root cause behind these crushing detours from our highest and happiest path, we’re doomed to repeat them.

If I boil down my own biggest mistakes along with the missteps others have shared with me that caused them the deepest pain, the top 10 would be these:

Not comprehending what you’re capable of

After reviewing thousands of responses from clients of my Career Path Self-Assessment, I can see how the vast majority of us don’t have a clue of our specialness and importance in the world. We’re crushed down by demoralizing experiences around us in our jobs and relationships, and we forget (or actually have never really seen) how our talents, gifts and passions are unique and so needed in the world. For 18 years in my corporate life, I never once had a glimpse of what I was truly capable of being, doing and creating.  It was only when the Universe kindly stepped in and helped me get so brutally ejected from my unhappy corporate existence that I finally “got it” and transformed my life.  Not understanding what you’re capable of, and how the world needs you and your gifts, is the most crippling of all mistakes.

Associating with and trusting the wrong people

There is no question that the people we associate with, and those we allow ourselves to be in relationship with, dramatically shape who we are and what happens to us. If the people around you don’t value, respect or care for you, or if they live by values that are in stark contrast to yours (and make your heart ache), your life can’t be what you dream it to be. If you want to soar like an eagle, then you have to take that huge leap of faith to surround yourself with eagles. (Thanks, Mo Faul, for that reminder.)

Letting your beliefs and fears around money stop you living full out

Literally more than 90% of the clients and colleagues I’ve connected with over the past 10 years (over 10,000) have a challenged relationship with money or some form of money trauma from their past. These challenges, mindsets, fears and blocks aren’t all about scarcity. I’ve met scores of people who’ve earned or inherited millions of dollars yet they don’t feel they deserve it, feel terribly guilty about it, or feel like impostors.  Others can’t believe that a happier life or career is in the cards for them, despite having a masters degree, and fantastic credentials and experiences. And others still dream of better jobs, careers and livelihoods but sabotage their own growth because of intense risk-aversion and deep fear around needing “security” and “safety” from money. Until you can untangle your money story and stop making money a ruthless God in your life that you need to feed and worship daily, you won’t achieve what you dream of.

Comparing yourself to others in ways that crush your confidence and life energy

I’m a fan of healthy competition, and believe it can absolutely fuel growth. But comparing ourselves to others and continually feeling “less than” ruins our lives.  If you’re constantly comparing yourself to others — other business people, colleagues, peers, family members, etc. — and come up short, your life will be drained of the confidence, energy and vibrancy you need to move forward.

Refusing to learn

When we’re going through painful, crushing times, there are critical lessons we’re meant to learn, but many of us fail to get these lessons. We miss the point entirely. In fact, if you feel yourself in constant regret about what you should have done in the past, you’re failing to learn the right lessons.  I failed to learn, for instance, that my deep unhappiness in my corporate career wasn’t because I wasn’t “good enough,” but because I was constantly pointed in the wrong direction, working on business outcomes that meant nothing to me.  The “right” lessons empower, uplift and strengthen you, not push you down.  If we don’t shift and change, and learn from what’s happening to us, we’ll simply continue to bloody our heads against the same brick walls.  We’ve got to learn new lessons and modify how we operate in the world in ways that thrill us, or we’ll never break the cycles of pain that we continually co-create.

Not understanding that you are separate from your thoughts

We are not our thoughts, and our thoughts don’t have to rule and control us. But they will control us if we have no awareness of what we are thinking and why.  Learning to separate ourselves from our thoughts is life-changing (mediation is a transformative tool for that – check out Lodro Rinzler for beginning meditation support).  The key is to learn to observe our thoughts, and create a separation from them so that with greater awareness and wisdom, we can choose how we want to react and behave in the world.  If we never gain awareness of what we’re thinking, we’re powerless to shape our reactions and behaviors.

Letting your ego and your need to be right wreck your peace, well-being and relationships

Our egos, and our need to defend our thoughts, values, and positions, can be healthy and helpful. But often, our egos run wild, and tiny sparks of narcissism can make us react in ways that burn bridges, sever helpful ties, and thwart our growth.  If you’re constantly looking for validation that you’re “right,” important, valuable, and if you feel the urge to drum out of existence people who don’t agree with you or who challenge you, your ego needs some work. After all, we simply can’t build the life we dream of if we cut off and alienate all our supporters, friends and advocates.

Ignoring your body

After years of chronic illness (in the form of a terrible infection in my trachea every few months for four years), I finally learned this: your body says what your lips cannot. If we ignore what our bodies are trying to tell us, we’ll suffer, and continue to suffer, until we listen and learn. And if we’re hoping to live a beautifully rich, happy and fulfilling life but fail to give our physical bodies what they need to be healthy, supported and nourished, we’ll fail to have the energy and vitality we need to make the impact we hope to.

Failing to stretch beyond who you think you are and what you’re comfortable in

In an interview I conducted with Herminia Ibarra recently on How Authenticity Can Keep Professionals From Growing Into Effective Leaders, I realized even more acutely how an over-attachment to “authenticity” can actually keep us from stretching and moving forward. If we stay only where we feel comfortable, even with regard to our self-identity, we’ll never get to the new destination that we dream of, because we fear it’s not who we “really are” yet.  The deep longing to stay put, and to feel “comfort” and “security,” creates, in the end, the most painful type of discomfort – the realization that we failed to fulfill our highest goals and potential. As Amy Cuddy shares in her powerful Ted Talk, at times you have to “fake it til you become it.”

Not doing the inner work to create the outer life you dream of

Finally, I’ve seen this in my own life and in thousands of others I work with – if you refuse to do the inner work on yourself to become stronger, wiser, more courageous, more competent, and less reactive, then the outer experiences in your life will fail to satisfy you.  A happy, joyful and fulfilling life takes work, and it starts with inner work – on your thoughts, insecurities, reactivity, negative mindsets, and fears. If what’s in front of you is making you unhappy, you first have to look inward to explore our part in it (we are 50% of what happens to us). If you refuse to identify how you’re co-creating your problems and your unhappiness, and shift it, you’ll continue to bring into your life exactly the same results.  And those won’t bring the peace, joy, and fulfillment you ache for.



16 thoughts on “The Top 10 Life Mistakes That Make Us Struggle Most”

  1. Excellent article. Kathy. You’ve captured some of the most valuable life lessons succinctly and I think I speak for many others when I say this really resonated with me. Well said.

  2. Thanks so much, Tikiri – so glad the post spoke to you and rang true. Happy 4th! and thanks for your feedback.

  3. Absolutely riveted by this article, it’s relevance, it’s articulation, and it’s “simple” truth. I immediately shared with those who have seen my recent ‘heartache’ and decision to leave my company.

    While I am ‘raw’ and still processing, I am definitely needing this type of reminder that I am not the only one who has hit the proverbial wall in corporate life.

    Thank you – I am going to read and re-read this, and then do the tough work ahead of pulling apart my individual and collective “mistakes” so that the road ahead is not so scary for me.

  4. I am doing the inner work and taking small steps. I haven’t lost sight of the big picture, but, sometimes progress seems slow and the prospects can seem daunting. It is hard work keeping negativity at bay. I think we all wish to see a quantum leap, without realizing that it takes many small steps to cross the mountain. Thank you for these helpful reminders.

  5. Thanks so much for sharing, Laura. I’m so glad the post was helpful to you, and motivating. Sometimes just knowing that the road we’re on has been traveled by many, many others can be soothing. Sorry to know there’s been heartache recently (I’ve been there, for sure), but there is light at the end of the tunnel. Hang in there, and keep going!

  6. Thanks so much, Chas. I believe you’re right – that we’re all wishing for a quantum leap, but we don’t realize that that leap actually comes from many, microsteps that get us there. Thank you for sharing.

  7. Incredible article as usual. Thanks for the wonderful article. In short
    Self Actualization & Self Realization happens when one aligns every area of life according to the inner or higher self.

    Remember Steve Jobs saying “Sometimes life hits you hard, Trust yourself or your gut feeling, intuition or karma”.

    Till we learn the lesson, the situation repeats itself. So, look at challenges as an opportunity to work on one’s inner self.

  8. Amazing article! It is definitely God inspired. Your article is deeply impacting my life right now as I am going through a major transition for my career…I am fighting against fear and negative thoughts every day because I have an interviewdecided to shift my career to a more fulfilling one. And many things are still unclear and uncertain as to how I will make it happen… Thank you so much for your great article.

  9. Thanks so much, Peggy, for sharing. I’m happy to know these words are having a positive impact, and helping validate your decision to move towards a more fulfilling path. Many things will be unclear and uncertain in the beginning – it’s a journey, but when we do it with our eyes, ears and hearts wide open, it can be so successful and rewarding. All best!

  10. Thanks so much, Shankar. Love your comment that self-actualization and self-realization happens when we align every area of our life with our inner and higher self’s guidance. Beautiful! Appreciate your insights.

  11. I’m stuck at a job that brings no value to my life and I feel like I’m wasting my time. Your article is another push for me to take action to change that. I’m currently working on my mindset that has been fixed for such a long time, reflecting all the points you made (not pushing myself intellectually, feeling insecure about my abilities, fear of taking risks…). I’m working on changing my mindset to grow, to learn and to change my outlook on life. It’s a challenge that I want to embrace. Thank you for your insights that are spot on the areas I need to challenge myself!

  12. Thanks for sharing, Anke. I’m so glad the post is serving as a “nudge” to get you moving to take action. It’s definitely time to challenge yourself, and it’s YOUR time to shine. Here’s a video of mine that I hope will provide some added fuel. All best.

  13. I stumbled upon your site by way of Forbes yesterday as I’m very much unhappy with my life and really don’t remember ever being happy in life. I’m closing in on 30 in Nov of this year and I notice I’m not cut for this rat race corporate life for a bunch of issues race,gender and persona just being a few. I want to branch out on my own but I know Im not some older professional with millions of years of experience. Things that come naturally to me is seeing the good in others,coaching others and researching ways to really do what one wants. I see myself in a few of the 10 and that hurts but is freeing all the same time.

  14. I always thought that mistakes are a set of mistimed-misdirected experiences, actions and words till I read this blog from you. Thank you Kathy.
    For me acknowledging and handling mistake was always a challenge, I hated to analyze my mistakes as I may over analyze it and beat myself up for it. The result, my whole life revolved around “Don’t repeat mistakes”.
    Your lines made this complex subject simpler for me and I am sure I will be able to pass it to my 7-year old daughter, who otherwise will face the same dilemma like me. I assume this is a 21st century skill that everyone should have and my daughter should get it from me. Warm regards!

  15. I have decided to take a leap into the unknown, starting a new business venture which I know only a little about, but I am interested.
    I will see where this takes me, it is very different from interior design, but as I am a business woman, well we will see, wish me luck Kathy. If you don’t try you don’t know and the opportunity could pass you by.
    Love Christine.

  16. So glad you’ve taken the leap, Christine! I wish you all the best. May I offer one tip today? As you mentioned you know only a little about this direction, please make sure to get the help you need to build a strong business, financial and marketing plan, with actionable, measurable goals and strategies for your new business. I see so many women launch new businesses then trip up and fall because they don’t have the right kind of help in their corner, or the business know-how required to thrive. I hope you’ll not hesitate to get help where you feel you need it. Don’t wait! Here’s a post today on just that – The Top 6 Reasons Entrepreneurs Fail To Heed Advice That Could Save Their Businesses. Hope that helps. I wish you all the best.

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