If not now, then never
Learning from a midlife leap into art, uncertainty, and the practice of courage
There’s no better way to really bring out the rational, scared, and doubtful parts of yourself than to quit your job to pursue a career in the arts and, in one fell swoop, invest all your cushion money into resources and support to accelerate your career in the arts.
Yes, I did this.
I am experiencing (and learning from) much fear and doubt.
How did I get here?
Let’s go back to November 2025 when I decided that I would resign from my post-doctoral position. I really wanted to give the gigging thing a try to build an audience and earn some money to keep recording. Up to this point, I had mostly taken the approach of sitting back and waiting to be offered gigs because the thought of spending all my time and energy searching for them was rather repulsive.
So I started doing a bit of research on some venues around western Canada that I know could host an artist like myself. I started cold emailing.
I heard back from a few of them, and booked two gigs from this attempt.
Overall, the response rate was not so bueno.
I also started applying for festivals for the summer of 2026- so far, I’ve received no word from any of those either.
A Facebook ad popped up one day in early February with a deal on a three-day workshop for how to amp up your gig-getting game. It was half price and cost me something like 80 CAD. No harm no foul, just some good information and pointers to be gained, I thought.
Fast forward to late February to the two gigs I had managed to book. They ended up not being, what I’d call, “good vibes” gigs.
The workshop started just after these gigs and I was feeling pretty disheartened.
As soon as the workshop started, though, I was taken in by the material- the facilitator was inside my head, describing what I was living and experiencing. The precision of the tools he gave us was bang-on. He identified many challenges and pitfalls that I had experienced and fallen into.
I liked the facilitator. I felt I could trust him. Good vibes guy. He was transparent in that he was indeed going to offer an opportunity to continue working with them at the end of the three days, but he promised the three-day workshop was going to actually provide real and useful materials and tools. And it did.
It delivered big time.
So comes the end of the workshop and the facilitator and I are chatting on WhatsApp (via voice notes, so I know it was him, a real person) and I indeed want to continue working with them.
I have been saying for the past six months, out loud to the universe, that I would pay someone to do all the stuff I don’t want to do: here was my opportunity.
Basically, I had a decision to make between two options.
OPTION 1: I had been given enough tools and material in the workshop that I felt comfortable I COULD do it all myself, implement this holistic gig-getting system. But this would be like a slow-bleed of time, energy, resources.
OPTION 2: Go big or go home, commit a ton of resources to this career experiment to accelerate the process, with me being able to be as hands off as possible in the grind of it and just focus on my craft. In addition, I would have weekly, critical, bespoke coaching support. In contrast to the slow-bleed of option 1, this is like a full amputation of resources and time, right out of the post-job gate. Six months of intensity. Six months of re-skilling. And if this doesn’t get the fly wheel going for me, then I will take a hint from the universe and finally settle into a more “responsible” career knowing that I gave it my all.
I chose option 2: full amputation.
I’ve come to the conclusion that my purpose in this life right now, my dharma, is to overcome fear and doubt. This context of pursuing music as a career, is but a vehicle for this.
I was expecting to work with fear and doubt over the next year, but I did not expect it to be so concentrated and intense right at the beginning of this new chapter.
This has real fire horse energy behind it.
But it feels right.
If not now, then when?
The voices of my “parts”
When I chose option 2, and released a big chunk of my resources to pay for this program, my rational part said things like:
“Perhaps getting the leaky basement fixed is a higher priority than this?”
“Well this will really dig into your savings which you intended on using over this next year to avoid having to go back to a real job”
“Okay we can move money from here to here and use these monies to pay for this and oh of course you’ll have other injections of income from other sources over the next while, oh but what about minimum payments, what about retirement?”
“We can ask so-and-so if they’d consider letting us do some casual work with them at their shops or in their businesses if they needed”
“I could go play music at the local coffee shop for tips each week”
Etc.
My fearful part said things like:
“You are going to lose this house”
“You’ll have to go hat-in-hand to your parents”
“You are going to have to live on the street”
“You won’t be able to buy food”
Etc.
My doubtful part said things like:
“Maybe you’re dad was right about joining the military?”
“What if this is a scam?”
“You might not be good enough to do this?”
“You might be too old to do this?”
Etc.
I have been sitting with these parts and their concerns for the past couple days, inviting them to the proverbial Buddhist “tea”. This is my practice.
Some observations from this “fear and doubt” -inducing experience
1. Drawing on our past experience for evidence is useful for grounding in moments of fear and doubt.
Here are a couple examples of my experiences I drew upon to support my conclusion that I am going to be okay and I’ve always made it work:
I recalled the immense panic when I took my first student loan out at age 23. The thought of having that much debt was crippling-- but I leaned into it and I began to view it as an incredibly important investment, and I never looked back. My education was a gift I gave to myself.
I had another bout of panic as I signed a year-long lease for my apartment in Vancouver in 2013. It committed me to 1250 dollars a month FOR A YEAR! Even then, to squelch the panic, I drew on my experience up that point. The evidence suggested I had never NOT been able to pay my rent as an adult. I always found a way without much strife or strategy, to be honest.
2. Taking stock of the time of life we are in and what is realistic to achieve moving forward as a call to action!
I am 43 years old. I am so fortunate to be healthy and aging well. I have intentionally created a life of very little obligation, with my only dependent being my dog. I have a skill set outside of music that has provided me my current circumstances of a homebase, etc.
But the truth is, I am older.
I am not too old to do music, no.
But I am too old to waste too much time trying to make a go of this as a career move.
This decision is me accelerating the process so that in six months I will have a pretty good idea of whether there’s anything here or not.
If not now, then never.
A good pop-culture self-help book that articulates this well is a book called “Die With Zero” by Bill Perkins. He argues the great case for using your money for experiences during the times of your life that you are healthy enough to enjoy them.
By the time we hit our 70s, 80s, and 90s, we won’t likely be taking expensive ski vacations or climbing Machu Pichu….or trying to gig around Canada and Europe.
And you’ll likely need way less fun money to live off of if you’re major pastimes are having tea, reading, and making puzzles.
3. “Maybe yes, maybe no” as a response to the recurring thought that “this is the most irresponsible/riskiest thing I’ve ever done” as a perspective-taking, power-move.
You’ve likely heard the Zen story about the farmer where, over a series of what appear to be “bad” circumstances, people comment on how bad it is for the farmer, his response to them is always “maybe yes, maybe no”. At one point, all the bad circumstances lead to his son not being eligible to be conscripted to the army for a war and people commented “isn’t that great!”. The farmer continues to respond with, “maybe yes, maybe no”.
So, maybe it is the riskiest or most irresponsible thing I’ve ever done or will ever do, but maybe it’s not.
There is a great balm in this equanimity.
4. The Essential Self’s response to the decision is extremely telling.
I have had a leaky basement for years.
Every time the snow melts, I spend three to five days on towel duty, rotating them from the floor to the spin and drain cycle to the dryer and back to the floor, every 3 to 8 hours.
There is a solution that I’ve been very close to paying for but I have not been able to pull the trigger on. Because what would it mean to purchase this solution? It would mean that I would have to finance said solution, taking on debt that would trap me in misery at my full-time, permanent job to be able to make payments.
Ayurvedic practices have interested me for a long time and I have considered doing some expensive courses this last year to become a practitioner. I also could not pull the trigger on that. It just didn’t feel liberating to invest in this, for some inexplicable reason.
But this decision to overcommit my resources to this intense six months in pursuit of the life I truly want to live? I will just make it work, no matter what.
Anyway, my point is that those other potential options for going into debt over something did not ignite in me the same energy to ‘just make it work’ that this investment decision has—so that tells me I’m on the right track to listening to my essential self.
5. ‘This is a career pivot and I am investing in re-skilling’ as an expanded perspective to this type of decision.
Sure, it isn’t trade school or law school or a data science master’s degree, no.
But I am viewing this as a 6-month training program.
I am viewing it as an investment into the next half of my life and career.
I am aware that it could lead to nothing after six months but, given it’s my art, that falls on me. If through this holistic program I haven’t managed to sell myself and engage audiences more broadly, then I never will.
Basically, I will know if I’m good enough at my art to make a go of this as a lifestyle and career in the next six months.
I can accept if the answer is no, to be sure. Then I can happily settle into and give energy to a different path that will unfold before me.
Ultimately, my mind has been on overdrive strategizing about how I will make this work.
But that is now my practice, to catch myself planning and strategizing from a place of fear. Then I turn my focus to ‘non-doing’.
For me, this looks like engaging and being present in grounding and supportive practices, such as:
Walking in the forest
Cuddling my dog
Practicing music
Yoga
Meditation
Sleeping
Brushing and flossing my teeth
Cooking meals
It is here in these moments, I feel I have enough and I am safe.