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Turning My Mess Into a Message – The Top 52 Mistakes I’ve Made In Life and Work

Part of Kathy Caprino’s series “Accessing the Most Powerful You”

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Bottom line – “Embracing and loving who I am and what I’ve done is not a fixed state – it’s a long work in progress.”

As many of my friends, colleagues and followers know, I’ve immersed myself in a 19-year life reinvention, and shifted from a very unhappy, lost and chronically ill corporate executive to an 2-time author, career coach/consultant, podcast host, speaker and entrepreneur who absolutely loves what I do for a living and what I’m focused on, despite the enormous bumps and challenges all along the way.

It’s been one heck of a ride, with pitfalls, bumps, highs and transformations, that I barely recognize myself from the individual I was back in 2001.  The core essence of me is still there, of course, but there’s been so much shifting and morphing that now I see much more clearly what I truly value and need to have in my life and work and family experience and how pursuing those authentic needs, wants and passions is a “finding brave” journey that changes everything for the better.

One of the positive outcomes of this journey is that I “get” myself a lot more deeply than I did before, and there’s a lot more self-acceptance and forgiveness of bad “mistakes” I made that hurt me and my life.

I need to state here that when I’m referring to “mistakes” I believe wholeheartedly that what we do that we later feel or experience is a mistake, was the best we could do at the time, with the information we had and who we were in the moment.

Often there was not another course that made any sense to us, so we took the path that rose up in front of us and felt like the best option. And often these “mistakes” are not errors at all, but simply detours that taught us something essential on our path to greater success, happiness, and reward, that transformed that path to something higher and better.

But, let’s face it, at the time, these missteps feel pretty awful when you’re in the vortex of them.

Eleven years ago, and the urging of a new friend, I decided to write down what I considered the biggest errors or missteps I’ve made in my life and work, as he mentioned he’d be really interested in hearing them. And that got me thinking… So I’ve decided to come clean with My 52 Mistakes.

Today, I thought I’d revisit these “mistakes” to see if these are still what I’d consider the most damaging, difficult mistakes.

Below is an updated look at what I consider the biggest mistakes I’ve made in my life and work thus far (most are exactly the same as what I wrote 11 years ago). I want to share them so you won’t feel alone in your mistakes, and you can learn from mine.  And I’m sharing these after working with thousands of professionals around the world, hearing what they consider to be their top mistakes and regrets as well.

I hope this brief look at the havoc each mistake wreaked in my life might be of help to you in knowing how universal these are and glimpsing how we can use what we’ve learned to leverage them for our growth.

For this to help as many people as I hope it will, we need more than just my experiences, we need yours – your stories, lessons, mistakes and breakthroughs – all of it!

We (particularly women) have spent a good deal of time in life going to great lengths to hide our mistakes — out of shame, humiliation and embarrassment. But I’ve found that it’s in sharing our missteps openly, without shame, that we can first empower ourselves as we see how universal and common they are, and then build a deeper community of colleagues, clients, customers, partners, and mentors who are “finding brave” as well, and who resonate with our own journeys and find hope in ours.

Here goes… My 52 Mistakes…

As a professional…

1) Letting my ego lead me around by the nose

2) Believing the myth, “Build It and They Will Come

3) Letting the “pendulum effect” rule my life (Waiting too long to take action, then being devastated and running to the opposite extreme)

4) Spending too much money on my business before learning how to earn

5) Listening to people who claimed to be experts but who are in fact full of s—t

6) Putting all my eggs in the Plan A basket without having a Plan B (yes, it’s very helpful to articulate and have a Plan B)

7) Holding back from sharing my insights, wisdom, and knowledge for fear I’ll give too much away for free or people may not like my messages

8) Not listening enough to my instincts and my gut feelings about people and directions

9) Ignoring my trusted colleagues and mentors when they said said, “The way you’re doing this isn’t working.”

10) Running around thinking I’m God’s gift to the world

11) Wasting time in the company of people I don’t adore and respect

12) Comparing myself to others instead of figuring out exactly what I want to offer, to whom, and why

13) Staying too long in a job I hated, not realizing it will eventually hate me back

14) Hiding from my fears instead of getting in the cage with them

15) Doing the same thing over and over expecting a different outcome (which is the definition of insanity, per Einstein)

16) Taking on a narcissistic “goliath” expecting to be a successful “David”

17) Remaining in toxic, miserable situations believing that I had good reasons to do so

18) Letting my salary define me

19) Feeling like an “impostor” because I didn’t know enough at the time (but could have gotten on the path to closing those gaps instead)

20) Thinking that this just “happened” to me– not realizing I co-created it

As an author/writer…

21) Assuming that writing a great book will always generate great money

22) Launching my book and work into a vacuum

23) Letting my accomplishments blind me to what I still needed to learn and know

24) Initially thinking my own personal story in overcoming career crisis was enough to be the basis of a bestselling book

25) Mistaking myself for a writer when I wasn’t writing and reading every day

26) Being obsessively wedded to all the vanity metrics of how the book was performing, including ranks on Amazon

27) Being overly attached to one idea, approach, story in writing the book that I thought was amazing (as journalists say, it’s time to “kill the baby”)

28) Hiding the deepest truth from myself about, “What do I want, and what do I really want?” in terms of outcomes I wanted from my writing and my work

29) Not having had the guts to say what I mean – to a whole slew of people

30)  Trusting the wrong partners in the process of writing, launching, and promoting my first book

31) Believing the hype of “experts” about the earning potential of coaching (sorry folks, there’s very little money in it unless you’re taking the right kinds of business, marketing, entrepreneurial, sales, niche development, financial planning and other actions)

32) Not having sufficient boundaries to protect myself from the pain of helping people who are suffering

33) Letting people walk all over me because I felt badly for them

34) Wasting months not liking my therapy work but thinking I should stay doing it (if you don’t like our your work and it’s draining and depressing you, there’s something important you have to change)

35) Believing having my new coaching business would be an easy way out of my miserable corporate job

36) Not understanding,” If you don’t LOVE your clients, you don’t love your work”

37) Stuffing myself into another person’s “model for change” when I wanted to create my own, unique one

38) Not healing my wounds sufficiently before being in service of others

39) Coddling my clients instead of helping them turn their mess around by themselves

40) Limiting myself to seeing only one way to make a living

As a woman…

41) Wasting precious time not speaking up for myself

42) Waiting for my Prince to come and rescue me (and being really pissed off when I realized no one could be that Prince)

43) Letting my mistakes devastate me

44) Being exactly the perfectionistic overfunctioner that I write about

45) Spending more time complaining about my situation than changing it

46) Worrying about polarizing and alienating people by saying what I believed was the truth (if you’re saying and doing what’s authentically meaningful and true for you, you will alienate people – get used to it)

47) Not understanding that trying to “have it all” often meant I’m working non-stop and so busy that my head’s going to explode

48) Waiting too long to find amazing, awesome people to connect and engage with

49) Believing I didn’t need or want great female role models

50) Letting my gender, generation, upbringing, traumas, cultural baggage, beliefs, fears (my “whatever”) keep me from accomplishing what I wanted to

As a human being on this planet today…

51) Listening to my mind (and to “rational thinking) to the exclusion of my heart and soul

52) Not understanding until my forties that I’m unique, special and powerful and can make the difference I long to make

*  *  *  *

OK, friends, your turn!  Did any of these speak to you? If so, which ones, and what one tiny, microstep or action can you take this week to address them?

Share your lists and your top three mistakes that you’re now working to overcome. (We’re getting honest here people!)  And please pass this along to anyone you know who’s committed to learning from their mistakes and experiencing breakthrough.

Feel free to contact me if you’d like to share privately.  Let’s do this together!  Let’s turn our messes into messages of honesty, forgiveness, and acceptance — and of bravery and power.

And all along the way, know that you are loved, respected, appreciated and valued for all that you are and have experienced – mistakes, warts and all!

Kathy Caprino, M.A. is a career and leadership coach, speaker, educator, and author of  Breakdown, Breakthrough and The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss. Kathy helps professional women build their most rewarding and impactful careers through her Career & Leadership Breakthrough programs, her Amazing Career Project course, Finding Brave podcast and free assessments and resources.

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