Starting Over is a Myth

Welcome to Musings. Where I share insights that have impacted me, thoughts on personal growth, and actionable strategies to help you navigate career and life.

Today: What does it really mean to start again?

This newsletter looks different because I’ve moved to Substack. A new beginning for me, though not without its endings. Which is exactly what I’ve been thinking about lately.

It’s September. It’s a new season. A new school year (our daughter just started junior kindergarten). Work picks up (ideally - or not). A new phase of life. New beginnings in all sorts of ways (Did you know that September is also one of the top months for divorces? But, that’s a topic for another day…)

My point is that, while September offers a lot of new starts, it also is a time for endings. Summer comes to an end. Vacations close off. The days get shorter. The grass stops growing as quickly.

As William Bridges writes, “We usually fail to acknowledge the endings, and so we stumble into the new beginnings half-asleep, clutching fragments of what we should have released.”

Bridges reminds us that we are always in transition - and when people or organizations come to me, it’s usually because they are on the cusp of change.

A common question people ask me, “What is it like to start again? How can I [leave what I am doing/change roles/adjust my approach]? I’m already too committed to start over.”

Or, “How can we pivot our business? We’ve already spent too much [time/money/energy] to change.”

Both of these conclusions rest on the sunk cost fallacy.

But, that’s not what I want to focus on today. What I think is more important to discuss, for now, is the question of what it actually means to start again. Are we ever, truly, starting over?

I would argue, no.

We are always carrying with us what we have accomplished, learned, felt and done to date. And that can be terrifying.

Take Daniel Plainview (Daniel Day Lewis) in “There Will Be Blood” (one of my absolute favourite films).

© Paramount.

Each time he expands his oil empire, it looks like a new beginning. But every “fresh start” is just another repetition of his obsession with power and control. He never really changes course.

So, yes - our past - our habits, our ways of being - can haunt us.

But, they can also help us.

But not every restart traps us in the same patterns. Think of Phil Connors (Bill Murray) in “Groundhog Day” (another favourite).

Yes, Phil goes through a lot of sh*t. Day in, day out. And, while the film might be a commentary on the redundancy of life, (and without spoiling it) it’s also a great example of how starting over (literally every day) gives one an opportunity to take (and use) the good from yesterday, for the better.

My point being: when we start again, there is an invitation to shift - to learn or unlearn a few things, to transform what we no longer need or want, to take what we know is useful, and - through the magic chemistry of will, awareness and practice - turn it all into something better.

For instance, right now, the beginning of a new season, I am working on developing programs, courses and other content (this new Substack being one of those projects). It’s daunting. It’s a new course of action that not only allows me to draw on all the good stuff I have in me, but also, requires me to confront a few important things. The voice in my head telling me that no one will read this. The little gremlin telling me that this coaching business was a terrible idea. The ghosts of my past saying, “Jordan, just go back to being a lawyer. It was so much eeeeeasier.”

Because, of course, starting again isn’t just about what’s next — it’s also about what tries to pull you back.

For me, the fresh start this season isn’t really about Substack or new programs. It’s about acknowledging the endings that need to happen first: the old modes of thought, the fears that no longer serve me, and the voices insisting I go backwards.

Bridges reminds us that beginnings require endings. So I’m choosing to end the habits that keep me stuck, refocus on what I know works, and move forward anyway.

Starting again doesn’t mean erasing your past. It means carrying forward what matters - and releasing what doesn’t.

So let me leave you with this:

What endings are you willing to face this season so you can truly begin again?

Are You At the Beginning of Something?

If you or your team are standing at the edge of a fresh start, let’s talk. Book a call below and we can explore what it might look like to begin again with clarity and momentum.