Jul 24, 2016

The 60 Day Radical Self-Care Challenge

Self-care is often seen as a self-indulgent luxury reserved for people with a high sense of self-importance, and that’s a problem.

It’s cool to be soooo busy. The societal narrative goes that it’s impressive to not have enough time to rest, play, or sleep well. The word ‘selfish’ has been demonized.

The fact is, you operate the best when you take care of yourself.

My Recent Experience With Burn Out

I’ve been building my business up full time for the past three years. And when I say full time I mean (unhealthily) more than full time.

Historically, I haven’t done too well with balance when it comes to work. I definitely lean more towards being a workaholic.

In the past three years I’ve written over 300 articles, eight books, and created three video courses, all while consistently serving my 1-on-1 coaching clients. Not only did I routinely not take weekends off (or even a single day off per week), but during phases of my business growth I would regularly and voluntarily work 12+ hour days, for weeks on end. As a rule of thumb, I would work my butt off until I got sick (i.e. my body demanding that I slow down) and then, as soon as I was semi-healthy again, I would continue chugging along at my usual workaholic pace.

All this is to say that I have been the furthest thing from the poster child for self-care that you could possibly be… which is also why I eventually learned that it was such an important lesson for me to learn.

My lack of self-care came to a boiling point when I lived in New York for April of this year. I have always considered New York to be the worldwide epicentre of striving. It is where the most driven people in the world go to make it big.

While I had a super-productive month in New York (pumping out 21 fully fleshed out articles), I left the city feeling beyond burned out.

I left the city with a heavy heart, an eye twitch, and a deep yearning to figure out and integrate my self-care routines once and for all.

It was on the plane ride home from New York that I outlined what would become the beginnings of my 60 day self-care challenge.


Flying home from NYC. Grainy cell phone picture. Self-care challenge: engage!

The Creation Of My 60 Day Self-Care Challenge

I once read a quote along the lines of ‘whatever you learn in the first half of your life, you should learn the opposite of it in the second half of your life’. While I hope that my life isn’t half over, I definitely feel like I’ve mastered (or at least overindulged in) striving/achieving/working hard in the first 30 years of my life, and so I decided to start leaning into ease, slowness, rest, and rejuvenation over the coming years.

While I believe that everyone’s self-care routines should be unique to them (because what relaxes me wouldn’t necessarily relax you), I think it would be beneficial to show you what the first iteration of my 60 day self-care challenge looked like, so you get an idea of what a self-care overhaul could look like.

My 60 Day Self-Care Challenge: The Rules

While some of the specifics slightly shifted as I went into my 60 day period, these were the guidelines that I originally set out for myself for my self-care challenge.

No TV – I was allowed to watch a limited amount of Netflix per week (mainly stand-up comedy), but I didn’t want to watch any television where I could be subjected to viewing commercials or evening news (which I feel are the most mind numbing/fear-based parts of modern TV).

No phone in bed (in the evening or in the morning) – my bedroom became a cell phone free zone. I plugged it in to charge in the furthest possible outlet away from my bed in my home. Because I wasn’t staring at the blue light and keeping my brain in productivity mode at night, this would give me higher quality sleep through the night… and because I wasn’t rolling over and checking my phone first thing in the morning I wouldn’t be starting my day in a reactive/anxious state of mind. Double-win!

No more than five alcoholic drinks per month – and if I do drink any alcohol, aim to have it be red wine. Also, if I drink alcohol of any kind I have to follow it up with a sugar-free electrolyte drink (like Nuun tablets) to replace the nutrients that I’m stripping away from my body.

Nutrient-dense green smoothies at least five days per week – this is the most nutrient dense habit that I have setup in my life. Super green smoothie. 80+% leafy green vegetables, with healthy fats, and limited whole fruits.

vitamix, smoothie, smoothies, smoothie recipes, self-care

Put effort into weekly meal prep – this would encourage me to eat at home more frequently and to know exactly what food was going into my body. Once a week I would make a large batch of chilli, curry, chicken stir fry, etc., and then portion it out for the rest of the week.

Eat a highly plant based diet – my body feels the best when I’m eating at least 10 servings of vegetables per day. Eating a largely plant based diet allows me to feel at my best on the physical and emotional levels.

Absolutely zero porn – I’m not against porn for moralistic reasons, but I don’t feel in integrity with myself when I consume any pornography of other people (i.e. not of me and my partner). I installed an adult site blocker on my computer and committed to viewing absolutely no porn throughout the two month self-care experiment.

Meditation – meditate for at least fifteen minutes, twice per week (minimum of 30 minutes per week total). Sometimes I’ll use the Headspace meditation app, and other times I’ll simply set a timer on my phone, lie on my back, and lead myself into it.

Prioritize daily laughter – whether I’m laughing with my friends, partner, or at a movie or stand-up comedy show, daily laughter helps me feel at my best. At the very least, I’ll watch a few minutes of stand-up comedy online to get in my daily giggles.

Daily sweating – I feel at my best when I’m sweating on the regular. Regardless of how I get my sweat in (far-infrared sauna, gym workout, dance break, sex, doing forty squats in the morning, etc.) I know that my body and mind operate at peak capacity when I’m getting the cellular restoration that comes from regular exercise.

(Here’s a short video of me dancing/warming up for my workout on a treadmill at 5am. Watch it for thirty seconds and you get to see me fall off of it!)

Weekly deep recharge self-care date – I have a few weekly rituals that help me feel my best. My most frequently utilized self-dates are going to a movie by myself, indulging in an hour long sauna, cleaning my house from top to bottom and doing my laundry, or going for an hour long float session and journalling afterwards. Knowing that these activities consistently make me feel amazing, I made it a priority to engage in at least one of these activities on a weekly basis.

Weekly dancing – I love dancing. As a writer and relationship coach, I am very often living inside of my mind… and dancing is one of the most reliable things that I do to get me out of my head and into my body. Some weeks that means I’ll go out and have a sober dance party in a nightclub by myself from 9-11pm (and then leave before the crowds arrive), and other weeks that simply means that I’ll put on one my favourite electronic music playlists and dance by myself in my living room.

Go out and meet new friends at events that I’m interested in – as a card-carrying introvert, it takes considerable effort for me to get out of my hermit-y bubble and go out and meet people. Experiencing such a thriving social life in New York reminded me of how much I wanted to cultivate a kick-ass social circle in Vancouver. I made it a point to intentionally grow the quality and quantity of my network within my first two months back, and the highest leverage place to start was to start going out to more events where my kind of people would be found.

Nude beach visit at least once per month – I love not wearing clothes, and I enjoy the beach a fair bit. One of my favourite parts about my hometown in the summer time is a small nude beach that I try to go to at least a few times per summer. But there have been summers where I was working so much that I neglected to prioritize any beach visits at all the entire summer. So I wrote my beach visits down and made it into a goal.

Weekly cuddling – I am very physically affectionate. My parents nicknamed me cuddle-bug as a toddler, and for good reason. So it makes sense that a minimum session of weekly cuddles had to happen as a part of my mandatory self-care. Cuddling/frequent physical affection has also been scientifically proven to reduce stress, anxiety, and your risk of heart disease.

(Do you love cuddling, you’re single, and yet you somehow want to incorporate cuddling into your self-care routine? Read this article.)

warmth, warm hands, blonde, paris, love, thaw, cuddle, cuddles, cuddle buddy, slow sex, 29 things, self-care

Only have coaching calls on set days – one thing that I did during the three years that I was prioritizing my businesses growth over my self-care was take coaching client calls almost around the clock. The client was in a challenging time zone and they could only do calls at 11pm my time? I’d do it. A client signed up and wanted to talk to me within three hours of signing up? I’d do that too (even if I had to cancel/shift plans with my friends in order to accommodate them). Talk about a lack of boundaries.

One step I’d never fully taken was allowing myself to only take calls on specific days so that my clients had to work around my schedule. This ended up becoming a key part of my self-care during this challenge.

Stretch my comfort zone by performing my first set of standup comedy – I was a huge stage performer during my schooling years (doing countless performances of music, theatre, and comedy) and I missed performing dearly. So I decided to sign up for a stand-up comedy class with a handful of strangers and see how it went. This was easily one of the most difficult parts of my self-care challenge, but not in the way that I expected.

(If you care to check it out, here’s a four minute video of me doing my first ever stand-up comedy set. I was super nervous and the audio isn’t the best, but you can hear what I’m saying if you listen closely. And, in case it doesn’t go without saying, it’s a little raunchy so this is not safe to be viewed at work/by children/by small dogs.)

Regularly play music with friends – there is a unique kind of flow that arises when people play music together. Many of my best friends in Vancouver are professional musicians and I enlisted a few of them to play music with me on a regular basis (even though the majority of them are far better than I am, it was irrelevant. The focus of the jam sessions was fun, not skill development).

No hanging out 1-on-1 with anyone who drains my energy – this point comes down to boundary setting. Sometimes you realize, after months of intermittently spending time with someone, that you just don’t vibe with them. One of the most self-care driven things we can do for ourselves is to regularly say ‘No’ to things/people/opportunities that don’t serve us or make us feel good. So I made it a rule to only spend time with people who I enjoyed being around.

Carry out any and all health related check ups that I’ve been meaning to attend to – that means going to the dentist, massage therapist, chiropractor, and anything that else that I’ve been meaning to get around to doing. Instead of continuing to allow these health concerns to slowly suck mental and emotional energy out of me on a daily basis, I decided that I had to carry out all of my health-related meetings within the sixty day period.

That’s it!

It should be noted (if it isn’t already apparent) that I’m not one to go by half-measures. If I commit to doing something, I’m doing it all the way.

Since my body and mind were already long overdue for some self-care, I figured that it’d be best to dive right into it and make up for lost time. It should also be noted that because I’ve been essentially working seven days a week for the previous three years, I already had enough business momentum behind me that I was able to cut back my work hours considerably (working about 20 hours per week) during this self-care challenge.

With my challenge laid out ahead of me, I embarked on my radical self-care journey for 60 days to see what would happen.

(Spoiler alert: to say that the results were surprising would be an understatement.)

(Side note: my overarching goal with the self-care challenge was to get to a point where I had what I label as “Bali-eyes”. Bali-eyes were what I had when I was so utterly relaxed and at peace with myself because I lived in Southeast Asia for three months.)


My 60 Day Self-Care Challenge Preparation

I sat down and got really honest about my situation. I decided to fully face what I wanted to change about the way that my life was setup.

I was tired of prioritizing my career advancement over my health. I was tired of saying yes when I wanted to say no and generally being a people pleaser. I was tired of sacrificing my health, sleep, and social life.

I wanted my new normal to be rest, ease, and enjoyment.

In order to be able to deeply commit to my new way of being, I made a few key steps before starting the self-care challenge.

1. I told the people who it would affect directly.

I told my clients that I could only see them on Thursdays and Fridays. I told my friends that I wouldn’t be eating out at as many restaurants over the following two months. I told my partner that I wanted to go out dancing and go to the beach more often.

Whoever would be affected by one of the changes that I was making, I gave them advanced notice to give them time to adjust and/or get excited.

2. I bought the necessary equipment in advance.

I stocked up on smoothie ingredients (for health) and electrolyte tablets (for hangovers). I paid for a software service that helped funnel my coaching clients into the appropriate days that I was coaching. I bought a multi-pack of sessions to be able to float at my favourite float place on a weekly basis.

If there was any physical good, service, or piece of software that marginally improved my life and made my self-care that much more attainable, I invested in it all up front. That way I would be in a good position to carry out my challenge without any avoidable barriers getting in the way.

3. I enlisted help from a few key people.

There were a few people who I not only had to inform of my new self-caring way of living, but whose help I had to enlist in order to properly carry out my challenge.

I signed up for regular coaching with a new therapist whose work I resonated with.

I reached out to two of my friends who I wanted to regularly play music with (they both said yes!).

I signed up for my stand-up comedy class with a long-time practicing professional stand-up comic.

After I had all of these people on my team, I felt like success in my self-care challenge was inevitable. I felt like I had a small army dedicated to my rest, rejuvenation, and play.

Now that I was set up for success, it was only a matter of carrying out the plan.

My Specific Experience With My Self-Care Challenge

Because I was overdue for some self-care, the first week was easy for me to sink into.

I played music with friends, took the week off from work entirely, and got a lot of high quality sleep, exercise, and nutrients into my body.

(Here’s a 90 second video of me playing music with one of my BFF’s)

For me, the real challenge started in the second week… since that’s when my resistance to self-care actually started to rear it’s ugly head.

I thought, “Well, I have some energy again, so I might as well use that to start being productive! Back to work I go!” But my body/heart/mind had other plans for me.

I knew that if I really wanted to make a deep level shift in how I related to my self-care, it was going to take more than a few days of intentional effort.

During weeks 2-6 I constantly found my mind trying to play tricks on me. It would try to convince me that self-care was overindulgent and that if I had any amount of energy to be putting towards my business, I should be using every last drop of it. But this had been my issue for the past three years. I would recuperate to the point where I had 20% of my fuel in my metaphorical gas tank, and then I would tell myself “If I have any energy then I must be fully back up to 100%,” which was never the case.

self-care, nude beach, jordan gray nude

Seven weeks into my self-care challenge, on a six day vacation with Amy.

The biggest overarching lesson that I learned throughout my self-care challenge is patience and persistence.

Shifting your relationship to self-care isn’t about being good to yourself for a weekend once or twice per year. It’s about fundamentally altering how you treat yourself on a daily and weekly basis. It’s about acknowledging the fact that you bring more to the world than simply what you produce (in the left-brained, masculine perception of productivity), and therefore you deserve to be healthy and to treat yourself well throughout your entire journey.

When you put forth a genuine effort to cultivate rest, playfulness, and self-care as a default way of being, your life begins to open up in entirely new ways. Your relationships become easier. You make new friends that are more aligned with your truth. You sleep easier, have better sex, and feel less stressed day to day.

Things That I Added Along The Way

Inevitably, some changes had to be made during my self-care challenge.

When I wrote up the original rules, I was writing down my intentions from a place of total self-care deprivation. I couldn’t have possibly known what I would need and what calibrations would need to be made throughout the process.

One of the biggest things that shifted was the total volume of what I expected myself to do on a weekly basis and the rigidity with which I approached the entire process.

The total weekly volume of my self-care activities needed to be changed for two reasons: (1) when I added up all of my activities, I had set up a ridiculous number of hours that had to be dedicated to my self-care and it made life unrealistic (making my self-care regime stressful and therefore defeating the purpose of my original intention), and (2) many of my self-care goals involved other people and their schedules, and I couldn’t control whether or not they would be able to meet up with me consistently on a weekly basis.

These two realizations allowed me to somewhat soften the inflexibility that I was bringing to my overall challenge. I wasn’t letting myself off the hook for accomplishing as much as I could… I was simply being more self-compassionate and allowing myself to sink in to the feeling of “I’m doing the best I can.”

How To Create Your Own Self-Care Challenge

First and foremost, self-care has to be personalized. What relaxes me might not relax you. Your self-care challenge has to fit your desires and your existing lifestyle… while also realizing that you may need to augment your current lifestyle to MAKE ROOM for more self-care.

Since posting on social media about my self-care challenge, I’ve taken on a few coaching clients and helped them to discover what they need in their own self-care journey.

Here are the questions and categories that they have found most helpful.

Three Questions To Ask Yourself To Create Your Self-Care Challenge

According to my clients, the three highest leverage questions I’ve asked are ‘What do you need to remove from your life?’, ‘What do you need to add to your life?, and ‘What have you been knowingly neglecting?’

1. What do you need to remove from your life?

Before you can add in new things to your life, you often have to create space by eliminating less helpful or productive things.

What people, hobbies, habits, or elements of your work life do you need to limit your exposure to or remove from your life entirely?

The first few things that come to your mind are a good indicator of where you need to start.

2. What do you need to add to your life?

With the space you’ve created by eliminating the negative things in your life, what would you like to now fill that space with?

What things bring you joy? What activities do you do that make you feel so entrenched in bliss that you lose track of time? What activities do you know you love doing but you’ve managed to not make time for them for several weeks/months?

Set intentions around wanting to add in or cultivate those new or returning things into your life and you’ll be better off for it.

3. What have you been knowingly neglecting?

Whether this question makes you think of things you’ve neglected adding or subtracting from your life, whatever comes forth for you deserves to be listened to.

Maybe you haven’t really been exercising for weeks and your body is feeling stuck, stagnant, and unhealthy. Maybe you need to reach out to a potential-new-best-friend but you’ve been avoiding the vulnerability inherent in the act of reaching out to someone. Maybe you have a mole on your back that’s been weighing on your mind for months/years and you haven’t called up a dermatologist yet.

Whatever you’ve been neglecting and for whatever length of time, letting that thing slip is like knowingly engaging in self-abandonment. Nobody was put on this planet to meet your needs but you. So if you’re neglecting yourself, then that slow-burning frustration is going to bleed out into every area of your life (your health, your relationships, your job performance) until you face it head on.

(Side note: if these three questions resonate with you and stir up a lot for you, you might also be interested in reading/bookmarking this article for later.)

Potential Categories For Your Self-Care Challenge

Many people find it helpful to have some categories to jot down their thoughts into. Use the following categories to spark your mind as to what you need to include in your self-care regimen.

Health – Daily Habits

What do you need to accomplish on a daily basis that would help you to feel more in line with your self-care?

A morning gratitude practice? Daily exercise and/or movement? Phoning one of your friends/family members every day?

The daily habits that you decide to lock in for your self-care will have a huge impact on your general well-being (especially if you decide to do the full 60 day challenge).

Health – Overdue Check-Ups

What have you been putting off? What do you know that you need to do?

Go to the dentist? Get a massage? Pay someone to do your taxes? Do a deep clean of your living space? Throw out/donate your old junk? See a chiropractor? Talk to a coach or therapist?

If it’s been weighing on you for months, it might be time to tick it off of your to-do list.

Your ‘Absolutely Not’ List

What things happen in your life that simply drain you of your energy? What do you know that you resent doing?

Are there certain people that you can no longer tolerate spending time around? Conversations/gossip that you can no longer engage in? Hobbies or activities that you need to drop altogether? Put it on the list, and hold yourself accountable to honouring it.

Setting appropriate boundaries is one of the highest leverage self-care activities that we can do for ourselves.

Outsource-It List

Are there any parts of your life that you don’t have the time/energy/desire to do anymore?

Many of our daily/weekly tasks can be outsourced depending on your budget, resourcefulness, and creativity.

Don’t want to prepare your own meals? Hire a food service that delivers to your door. Don’t want to do the deep clean of your house anymore? You can find quality housekeepers for under $100 and have them over once or twice per month. Sick of doing your own laundry? You can drop off your clothes at a laundromat with ‘wash & fold’ service for $10-20 and save yourself hours in the process. Do you feel like going on a vacation but you don’t want to do all of the heavy lifting of the research? You can use a travel agent, or hire a virtual assistant to do all of the research for you.

If you don’t like doing something, you probably don’t have to do it. Outsourcing is a great way to save yourself time and the hassle of doing things you don’t enjoy.

(Side note: don’t outsource things just because you can. Only outsource things that you don’t enjoy doing. If you find cleaning your apartment or doing laundry to be fun, meditative practices, then keep doing them! Only outsource that which you can afford and that you would rather get off of your metaphorical plate.)

Relaxation List

What activities consistently bring you peace and relaxation?

When we’re the most stressed out, it’s easy to forget about the core activities that bring us the most joy. I find it helpful to have a short list of your favourite self-care activities all in one place so that you can reference them when you need them the most.

You can either have your favourite activities in a digital document (on your phone, on your laptop, etc.) or (my preferred method) you can print off a physical piece of paper and put it somewhere where you’ll see it. Put it on your wall. Put it on your fridge. Put it next to your bathroom mirror. Just put it somewhere where you’ll see it so that your self-care and relaxation will never be far from your mind.


Similar to the previous section on relaxation, I find it helpful to have a short-list of my favourite ‘fun’ activities. My personal examples include playing trampoline dodgeball, playing music with friends, and practicing stand-up comedy. What would your ‘fun’ list look like?


What nutritional changes need to look like in order for you to feel more congruent in your self-care?

Do you need to cut out coffee/caffeine/refined sugar? Do you need to start drinking green smoothies more frequently? Do you need to start eating in more often? Do you need to start taking vitamin supplements in specific areas that your doctor told you you’re deficient?

You know what you need. And if you don’t, maybe it’s time you visited a nutritionist/dietician to discuss your health habits.


Your sleep hygiene is an important aspect of your self-care. You sleep for roughly a third of your life… so it’s probably something that you should get good at.

Do you need to invest in some heavy-duty blackout curtains? Are you still staring into your blue-light omitting digital device right up until you try to go to sleep? Do you need to start prioritizing a consistent bed-time to ensure that your body’s natural rhythms are able to star syncing up again?

Quality sleep positively affects everything in your life (your work, your sex life, your relationships, etc.). Make it a priority.


Many studies have shown that the #1 determinant of your happiness is being a part of a tightly-knit community of people that love you. And while some people thrive in highly isolated, monk-style life setups, they are certainly the minority.

How could you invest in your closest and healthiest relationships further during your self-care challenge? What friends do you need to see more of? Which friends do you need to see less of? Which family member are you overdue to meet up with?

Quality intimate relationships are an important part of a well lived life. If no other ideas come to you of how to incorporate personal relationships into your self-care routines, start by asking a couple of friends to join you in one of your most fun/playful activities (sports, music, going to live events, etc.).


It’s hard to feel like you’re taking genuine care of yourself if your work life feels massively unfulfilling.

If you’re currently working in a job that drains you on a daily basis, then it might be time to reconsider your approach.

It has been scientifically proven that you’re happier making $40,000/yr. doing a job that you love, than making $200,000 a year doing work that you hate. Money/perceived social status doesn’t magically make up for the gap in your happiness. Or, as my main man James Oppenheim once said, “The foolish man seeks happiness in the distance. The wise grows it under his feet.”

Do work that you love today. Even if you have to do it on the evenings and weekends around your day job. It’s not always easy, but it’s worth it.

Your Self-Care Challenge Begins Today

I could come up with a formulaic structure of how you could go about blocking out your unique self-care challenge, but I really think that it has to be so individualized that only you know what you need to do.

So I hope that this article provided a framework for you to begin re-prioritizing your self-care in a more significant way.

My hope for you is that my lived example has given you a boost of motivation to care for yourself (even 5% more) on a daily basis.

And if you enjoyed this post, you’ll likely also love checking out the following resources:

7 Simple Life Skills That Improve Everything

11 Easy Ways To Actually Love Yourself More

How To Overhaul Your Entire Life In 5 Easy Steps

21 Of The Best Self-Care Practices Ever

The Greatest Health Investment You Could Make (Vitamix Review) – the ultimate list of smoothie resources!

The Art Of Extreme Self-Care by Cheryl Richardson – a book with a funny title that I thoroughly enjoyed on the topic of self-care.

The Mindful Path To Self-Compassion by Christopher K. Germer – another book that I found helpful in my journey with working through negative self-talk

Dedicated to your success,




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