Leaning in To Letting Go

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“The only way to make sense out of change is to plunge into it, move with it, and join the dance.” – Alan Watts

It seems like for every lesson I’ve learned in my life, I can trace it back to a particular story. Is that a sign of middle age? In this case, I’m thinking of the lesson of learning to let go and a consulting project I did for Microsoft about 25 years ago.

My colleague, Bill, and I were assigned by the consulting firm for whom we worked to write a white paper for a client at Microsoft. It was the late 90’s and Microsoft was in that phase where it was growing so fast that there wasn’t a lot of process but instead a lot of hard-working but perhaps egomaniacal cowboys.

Our assignment was to write this paper about how a group of these cowboys rolled out a new email software at Microsoft. Bill and I were experienced at deploying that software and had published a book about it so theoretically, this project should have been a snap.

After interviewing the key players, we drafted the paper. They hated it. We revised it. They still hated it. They would call us to meetings to tell us in detail how much they hated it. The problem wasn’t the technology – it was that we didn’t get the tone right. We didn’t think they were as cool as they thought they were so we missed the mark over and over again.

I can’t remember how many versions of that paper we wrote. Maybe five? But after torturing us for a while, they finally fired us and wrote it themselves. It hurt. I felt like I’d been at a rodeo and had hung on way too long.

I went on to learn that lesson about letting go in many ways as a consultant. I’ve found out that no matter what kind of a job that you are doing, if the person that hired you is replaced by someone else, you will most likely get replaced too.

I’ve hung on too long in those cases as well – trying to pretend it’s not going to happen. I’ve been sure I can make the new person pick me, and like a puppy at the pound, try to do any number of tricks to prove I’m likeable and reliable.

I’ve also done the opposite and just walked away when the staffing changes happen. Finally, I’ve figured out that when the changing of the guard happens, I say, “Here’s what I’m working on. I will continue to support it in whatever way works and if you prefer to have someone else do it, I will facilitate that in the smoothest way possible.”

It’s so natural to want to cling when things are coming to an end. Sometimes, it really hurts and is scary. I’ve found that acknowledging that, feeling it all the way through, helps. Because projects, groups, and companies, like life, have a cycle. I’ve come to learn that to stay loose is the best way to ride the current. That way, I’m ready to lean in to the next thing that comes to fill the opening. Because that happens too.

Leaning in is just one of the things I’ve learned to do the easier way. For a mountain climbing story that taught me the difference between doing things the easy way versus the hard way, check out my piece on The Heart of the Matter: Doing It The Hard Way Or the Easy Way

(featured photo from Pexels)

40 thoughts on “Leaning in To Letting Go”

  1. Pingback: Doing it the Hard Way or the Easy Way – The Heart of the Matter

  3. I know you have different and hurtful memories working for Microsoft but I do think it was still pretty cool that you got to experience that at their rise – egomaniacal cowboys and all.

    I agree that being ignored, not selected and being let go are all very devastating things especially when the wound is so fresh and raw and you poured a lot of heart and energy into the relationship, be it work or personal.

    There is something to be said about letting go and finding freedom and recovery in that. And then realizing maybe things worked out as they should’ve!

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    1. I love your compassion, Ab. And I totally agree about working for MS in those days – I have great stories about parties and innovation as well. 🙂

      You are so right about that moment of realizing things worked out as they should’ve – exactly right on!!

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  4. Getting fired sucks, but it can it lead to better things. My experience of getting fired gave me both the time and the motivation to go after the work I really wanted to do. It sounds like you have a great plan for dealing with the volatility of having to work/not work for clients who change leaders mid-project.

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  5. Letting go- so hard to do so much of the time, even when we know the inevitable answer must be to move on. Human nature maybe- to feel the need to fix things; remain committed to a phantom outcome even when we know we’ve probably done our best and it’s time to let go… Great life lessons in this story Wynne, especially being proactive and using the wisdom you’ve acquired to preemptively open the door if change is needed.

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  6. What keen observation: projects, groups, and companies, like life, have a cycle. I’d never considered that but, now that I think of it, I’ve noticed the same. Sometimes it takes painful rejection to recognize that we deserve better that to be around those who can’t see our value, and moving on from the relationship was likely inevitable from the start.

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    1. What an excellent point that the pain sometimes wakes us up to the reality the outcome may have been inevitable! And thank you for the note about the cycle of things – funny how we come to see it.

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      1. I’ve noticed the cycles in my life re jobs too, and while it may have been difficult or painful at times, another door always opened. Sometimes it’s good just to be able to hold onto that until things get better!

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  7. Your post today has opened my eyes to how fortunate I was to have missed the corporate or consulting world I was headed for simply because of an unanticipated move to a smaller place, and instead found myself in a career built in a nurturing community of colleagues. That aside, your lessons learned are valuable in all work environments, and in life situations.

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    1. A nurturing community of colleagues – wow, that sounds wonderful, Jane! I’m so glad to hear of that experience for you and that you share the lessons learned from that vantage point as well!

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  8. I love Deb’s reference to hoped-for, “phantom outcomes”. You aim to be positive and proactive in all aspects of your life, Wynne, but the cowboys (and cowgirls 😉) can break us if we don’t know when to retreat, disengage. I find there’s a thread here about knowing your worth, too. I connect with that! 🥰 xo!

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    1. That phrase grabbed me too! Yep, time to retreat and disengage – well said. And your observation about knowing our worth – that’s a great one too. Thanks, my dear friend! ❤

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  9. My thinking, I believe, was going along the same lines as Vicki. It seems like you’ve learned some good from your experiences. You, as a consultant have more power and control than an employee. Plus being able to recognise the change means further changes and offer to help with any transition will also contribute to a better reputation for how you handle clients and impact on future contracts.
    Not everyone has the maturity to behave like an adult in these situations, kudos to you Wynne.

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    1. Great point about having more agency as a consultant. That’s true. I’m really laughing and loving your comment that “not everyone has the maturity to behave like an adult in these situations.” Right! Thanks for the kudos and kind words, Brenda!

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  10. Sometimes people take the harder path because perhaps they learn more from experience than theory.
    Sometimes it’s the joy of the challenge. I’ve often lived by Frost’s poem, “two paths diverged in the woods and I, I took the one less travelled by, and that has made all the difference.”
    The secret is knowing that precise timing of how long to hang on and when to let go. That comes with experience and looks like you’ve got it down.
    Great insights Wynne.

    Liked by 2 people

    1. Oh, I love your tie to Robert Frost, Alegria. Yes, the timing of how long to hang on. It does come with experience – and I’m not sure I get it right. But you are spot on that it gets easier. Thanks for the great comment!

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  13. I like when you called egomaniacal cowboys the people you were working with. It gives me precisely the idea of the kind of personality they might have had. Sometimes it is definitely better to let go. Then you can build up your experience as you have wisely done Wynne.

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  14. Did they ever tell you why they didn’t like the previous/any of the revisions? Could it have been a case of the messenger getting “shot”? Maybe they weren’t ready to hear the message and were looking for a pat on the head rather than the truth?

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    1. Such great question, EW! I think that’s why it took so many revisions before we got fired. They couldn’t quite come out to say that we didn’t revere them enough – although I distinctly remember one guy said in an interview, “I am a God here at Microsoft.” They wanted less of a white paper and more of a super-hero tale. It was all a little cartoonish… 🙂

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  15. the art of holding on loosely….Love your example here Wynne, I’ve had no experience in the corporate world,so it’s fascinating. (and could be very humbling and painful. God uses the every day stuff all of the time to accomplish His end goals in my life.

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  16. Life is funny sometimes! This is exactly the message I needed to hear today Wynne. I was feeling a little down this morning (probably a little sad for myself) and I saw this post ….. five different edits, oh yes, work has nothing to do with performance or blue ink or black ink, it is what it is. I can take it all in and be resilient or I can choose to try to make everyone like me and make it personal. The better way for me personally is to look myself in the mirror and move on. Thank you Wynne, really appreciate this!!!!

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    1. I love that this resonated. It’s such a hard lesson – but a freeing one. I love how you put it “The better way for me personally is to look myself in the mirror and move on.” Well said, my friend! 🙂 ❤

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