Chapter 1: A guy named Bill, a radical observer

Sometimes in life you meet people who change the course of your life drastically and for the better.  I’ve luckily had the chance to meet a few of these people in my life already.

Bill has been one of those people for me.

I met Bill in late 2016 when I was attending a course he was offering.  I LOVED this course.  I loved it for a number of reasons, though one of the main ones was because this guy simply exuded JOY for his work.  He was smart – really smart – and had been running his business for multiple decades.

He helps people improve their sales outcomes, primarily through radical self awareness (yes, the word radical is going to be a theme here).  He was challenging all of our notions about sales – how we engaged with our pipeline, how we approached calls, and how self-aware we were during this process.  I took every chance to talk to him after the course each day – I remember thinking to myself, ‘I want to BE this guy’.  Not literally of course (!).

At one point during a role play with a neighbouring student, I made a comment and he looked directly at me for a moment.  It was one of those looks where you know the person has SEEN you, exactly as you are – every strength and every limiting belief.  One of those ‘looking into your soul’ looks that few people are capable of. He then made one comment to me and one comment to my neighbour – giving us each something to consider about ourselves – and then continued on completely un-phased to the next part of the course.

Holy mo-ly.

That one comment taught me so much about myself.  I couldn’t stop thinking about it for days. Actually, it was more like weeks.  I realized it was one of my limiting beliefs and I saw its threads running through a few areas of my life.  It also reinforced how much of what we unconsciously reveal about ourselves through the language we choose.  This was really the kicker for me – it was something I had known subconsciously and was completely crystallized for me in that moment.  Realizing how much of our beliefs we portray through the words we choose also helped me a lot in all of my sales calls. Win-win, my most favourite situation.

I left that course totally energized. It set me up for 2017.

My new gig wasn’t playing itself out quite the way I had hoped.  It’s a long story that most importantly, left me questioning a lot of things.  For a while now I’ve treated my career as my business, even when working for someone else.  It hasn’t been perfect, though it’s been pretty great and has lead me to lots of places, to meet so many amazing people and have a lot of challenges that continuously encourage me to grow.

This particular challenge had me zooming out to think about my long-term goals. Was I on the path that I wanted to be on? Was I working for myself? I wasn’t quite sure any more, though I wanted to make sure I was.  My first move in 2017 was to hire a professional coach – Bruce, a deeply skilled, positive guy that I had worked with briefly the year before.  His questions and reframings have been invaluable in helping me get clarity and steering me where I wanted to go. A skilled professional coach is an investment.

Bruce has been the other major influencer this past year for me.  One of my fears in leaving a position early was – similar to many people’s fears – what people would say.  Like many others, I value others perspectives – while also recognizing that it doesn’t have to define me.  I worried that people might look at me as a job hopper or that I was taking the easy way out.  Neither of those were true for me.  I knew I wasn’t a job hopper – since leaving an organization where I worked for 5 years, I had spent about 2 years working primarily on a contract basis.  This of course means short-term gigs.  Walk into an organization, tackle the challenge you were hired for alongside others and then help manage the next step of change as you leave.  It has been fun and has taught me A TON. I also knew I wasn’t looking for the easy way out – and that definitely proved true, things were about to get a whole lot more difficult before they got easier.  I had luckily read Seth Godin’s The Dip (yes, I’m a superfan), which helped me frame what was going on.  [Blog post on the dip here, though I definitely also recommend the book, which is a super quick read].

When I took this new gig, I knew I wanted to focus on sales skills. I saw it as the next step in my ‘field learning’.  I’ve always tried to take jobs, projects or volunteering that would help me develop a skill set I wanted to develop while working for organizations whose missions or values were aligned with mine.

Sales was the next step for me. I had done a fair bit of fundraising and wanted the chance to refine my sales skills – it was part of my long-term plan.  That’s what lead me to sitting in Bill’s course.

Bill is a radical observer.  Like just so far ahead of the curve it’s unbelievable.  He has the ability to see you (like really see you) through asking you a few questions and listening to the way you respond.  He is a master at reading people and more importantly, based on those observations, of providing real value to you or your organization.

[I’ve been liking this word ‘radical’ lately.  Cheryl Strayed introduced me to radical empathy in ‘Tiny, beautiful things‘.  Ray Dalio’s ‘Principles‘ are a deep dive in radical transparency and open-mindedness.  While I think ‘radical’ is on its way to becoming an overused buzzword, I’m going to embrace it here as a simple word that, when paired with another, can convey a lot of deep meaning].

Bill gave me the gift of helping me see me how others might see me, just a little more, and helping me see a limiting belief – the gift of what Ray Dalio would call radical transparency.  Delivered with firm gentleness that challenged me to grow.

As I thought about this limiting belief in the early part of the year, along with my 2017 intention of not rushing, and I realized I had some time to set myself up for what I wanted.  I hadn’t quite strayed from the long-term goal I was working towards, but I was about to.  It was time to get back on track.  I started reaching out to chat with some people, and worked closely with my coach to hatch 3 shorter-term goals:

  1. Start working for myself again (which I could do within the organization I was already at by radically owning my workflow).  I would constantly remind myself of where I was going and why, and how this experience could be a living lab for me.  That changed everything.
  2. Get ready to liquidate my assets to increase my flexibility, and
  3. Travel for a few months before diving more fully into my next thing.

I decided on purpose to not attach a strict timeline to these.  Maybe I would get these all done in 2017, and maybe it would take me longer than that.  I wanted to remain open to opportunities and I had a few other things I needed to work on at the same time.  By nature I’m a planner.  I love planning, I have lists, I have spreadsheets, inbox zero gives me a dopamine hit.  But I’ve been a planner long enough to know that nothing goes quite according to plan, so it’s best to always focus on the goal and remember that there are multiple pathways there.

Coming up tomorrow, chapter 2: Getting ready or getting ready to get ready? A skydiving preflight checklist.

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