My 5 F*cks: How I Turned My Life Around Before Founding My Remote Business

This is the story behind my story


Welcome to Remotely Inclined, a newsletter about remote work and remote entrepreneurship. If you’d like to sign up, you can do so here. Want to share your feedback? Take this short survey. Or just read on…

First: a HUGE welcome to the new community members - our little community grew by about 100 people since the last post went live.

Second: In remote work news, Slack just announced it’s going permanent remote. It’s a masterclass in empathy, as the announcement is that employees get to choose whether they stay remote post-covid or if they go back into the offices. I’m sure Slack will eventually downsize their office commitments, but I love that they are starting with people-first. It’s the right way to do it.

Today’s story is a bit of a departure from the usual remote work-this, remote business-that. A reader asked me about my five fucks system that I mentioned in last week’s post on creative systems for remote teams, and I wanted to share that with everyone. 

The failures I experienced - and then building the My 5 Fucks system to turn my life around - helped me get out of debt, lose 70 lbs, and led to me founding my remote business in 2017. 

This is the story behind the story. I hope you like it.

I started my first business when I was 23, in late 2015. I’d read a bunch of business books growing up and thought I was cleverer than everyone. I can’t stress enough how wrong that mentality was.

By the end of 2016, the business was an unmitigated failure and I knew it couldn’t go on. I spent $40,000 - $25,000 of which was my life savings from working all throughout college and $15,000 of which was debt - all without a single dollar of revenue to show for it. I was struggling with mental health issues as a result of the failure and had zero resources to do anything about it. I also ballooned to nearly 300 lbs (which, even on my 6’4 frame was very overweight). Oh and I was painfully single / had no confidence in dating. Much fun.

In the moment when it hit me the extent of what I’d lost, I seriously questioned if I’d ever be successful in life. I didn’t doubt my ability to survive. I was lucky enough that if I needed to move home, I could. But I was genuinely worried I’d never be a success, having so solidly fucked up at a young age that I’d irreparably destroyed the foundation of my career and financial life. 

The origins of giving a fuck

So, we’re at the beginning of 2017. All fresh hell unleashed: no money, depression, no business (or job), no boyfriend, and incredibly overweight. 

In between lamenting my crap scenario and emotion-eating, I stumbled upon two articles and a book:

James Clear talked about building systems of habits - basically, knowing where you want to go but focusing on the inputs you need, not the outcomes you want. 

The article about the entrepreneur focused on her prioritization framework of picking a few ‘non-negotiables’ in her life and being ok with the rest of life falling where it may. For her, the non-negotiables were things like having dinner with her kids every night (she’d plug back into work later in the evening) and caring for her ill mother. She talked about being ruthless about non-negotiables, but flexible with everything else.

Mark Manson talked about assuming everything was your fault because if something was your fault, it meant you had control over it. 

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Designing My 5 Fucks

These three concepts (systems, non-negotiables, and owning your faults) struck a chord with me. Leveraging all three concepts in December 2016 / January 2017, I developed “My 5 Fucks,” something I buzzword-ily called an ‘automated personal development’ system. 

The system had three tiers

  1. Category

  2. Personal Descriptions

  3. Action items

The initial categories

I took stock of everything that was crappy about my life (that is to say: basically everything at the time) - and ended up with four categories I wanted to improve that felt comprehensive yet specific: 

  1. Physical Health

  2. Mental Health

  3. Financial Health

  4. Relationships Health

Since I had already pre-committed to “My 5 Fucks” as a name (because it sounded cool), I racked my brain for a fifth concept. I’d read somewhere that humans remember lists of either three or five items better than four, so I wanted to stick with five if I could.

Then it kinda hit me: rest. Recuperation. I needed to build that into my life. I also thought about the huge obstacles I had in front of me in the other four areas, and realized that at any point I would likely need to dedicate more effort to a specific fuck. 

So I settled on the fifth Fuck: The Emergency Fuck. 

This way I guaranteed that 20% of my capacity was floating and could be used as needed, whether to bolster capacity on the other four fucks, deal with a genuine emergency, or use the capacity to rest. It turned out this would be my saving grace more than once.

Personal descriptions

Based on what I’d read in the articles (particularly James Clear’s note about systems), I knew that I had to have some general yet definite definition of what each fuck meant to me. It had to be specific enough that it was a concrete, achievable thing. 

Yet at the same time it couldn’t be so specific that it pigeonholed me into only one definition of success. A common example of this is around weight. A LOT of people obsesses about a number on the scale when what they really want is a feeling - looking good, feeling comfortable in their body, or that feeling of putting on a fitted shirt and not feeling self-conscious. 

So I came up with the following: 

Physical Health → “Look good”

Mental Health → “Feel good”

Financial Health → “Enjoy life and reset my foundation for the next 2-3 years”

Relationships → “Grow and help others grow” 

Emergency Fuck → “Loaned out one at a time for life’s emergencies” 

Given how horrible I felt about everything, I didn’t have the mental strength to get any more specific than those things at the start.

Action items

No system works without action. But I also didn’t know what action items were good for these things, since there are a lot of ways to achieve all of those fucks. 

So I set a parameter: “Action items are defined as things that, if I do them every day, I am living like I give a fuck about the things I say I give a fuck about.” 

And the second parameter: It had to be something I knew I could do the moment I wrote it down. Let me be clear: action items must be 100% practical from the moment you write them down

So we get action items:

Physical Health → “Look good”

  • Eat less overall

  • Anchor all food in protein and veggies

  • Drink 3-4L of water a day

Mental Health → “Feel good”

  • Every night, name one thing I did well and one thing I can do better tomorrow 

  • Invest in my hobbies

  • Read more

Financial Health → “Enjoy life and reset my foundation for the next 2-3 years”

  • Spend only on necessities

  • Save as much as possible (wrote a monthly average savings target based on my income)

Relationships → “Grow and help others grow” 

  • Ask other people their experiences to learn from them

  • Focus on delayed gratification

Emergency Fuck → “Loaned out one at a time for life’s emergencies” 

  • Used as needed 

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Off to the races

Nothing happened for about a month or two. Then my grandfather fell, got very sick, and was admitted to hospital in February 2017. At the same time, I realized I wasn’t making enough doing ad-hoc freelance writing to meet my savings goals so I started applying for jobs. 

Suddenly, my emergency fuck was dedicated to my grandfather and the full force of my financial fuck became dedicated to finding a job. 

I ended up getting a job that I started in April 2017. In my first week on the job, my grandfather died. My emergency fuck went back onto the shelf after the funeral. 

Two weeks later, I was stopped at an event by an entrepreneur who said “I love your writing. Can I pay you to write for me?”. The next day, I received an email from a different entrepreneur - someone who turned me down with my first business - asking if I did content consulting and if I would help them. 

I kept my financial fuck focused on my job, but moved my emergency fuck to focusing on my burgeoning side-hustle, which needed to be remote since I had a full-time job (that I had no intention of quitting at the time).

As I was setting up my side-hustle, my relationships reached what I would officially call a low point in about July 2017. After a few very, very bad experiences, I made two decisions:

  1. I needed a break from dating. 

  2. I needed to edit my relationship fuck. 

I changed the definition from “Grow and help others grow” to “Be vulnerable and let people in.” I also added the action item to “whenever possible, choose vulnerability.” I then immediately took a 4 month break from dating. 

Also in July 2017, I got a random reach out from someone on Instagram. I’d just followed him and he thanked me for the follow. 

He then said “If you need personal training ever, let me know.” I said I was interested. The only problem? Money. My job was earning me enough to pay down my debt and my side hustle was making just enough to let me save a bit. I couldn’t start spending money on personal training. 

At this point, my emergency fuck was back on the shelf because managing the side-hustle had become an easy habit. So I picked it back up and used it to focus on growing the side hustle enough to pay for my personal trainer AND let me save. I started working with my personal trainer in August 2017.

Within a week of setting that intention, I got an unexpected call from one of my clients. They had a massive project that no one else was available for. They would need me to start immediately and finish within a month, but the pay was good enough to cover 3 months of personal training plus continue to save. Because I had already planned my emergency fuck capacity to this project, I was ready to leap. 

Around November 2017, I tried re-downloading a few apps to give dating another shot. Armed with my new intention to be vulnerable, I was more upfront about wanting to get to know people instead of just hook up. If someone wasn’t interested, I simply backed off and moved on. In December, I started chatting with the guy who would become my boyfriend (and still is as of me writing this, over 2 years later). 

Results across the board

In so many words, the system worked. I took stock of changes at the end of 2017, 2018, and 2019. Here’s what happened: 


  1. Physical health → Working with a personal trainer, down 30 lbs.

  2. Mental health → Stronger from the confidence of gaining strength / building a small side hustle.

  3. Financial health → Making enough from my job + side hustle to live (VERY cheaply), pay down debt, save a small amount, and pay for my personal trainer.

  4. Relationships health → Learned to be open and direct with what I want, had started some genuine dating possibilities.  

  5. Emergency fuck → Used to handle my grandather’s illness and death then used to focus on my side hustle so I could pay a personal trainer + save money.


  1. Physical health → Lost a further 40 lbs after continued work with personal trainer

  2. Mental health → Continued to gain confidence along with business success / weight loss. Spent my 2017 and some 2018 savings on hiring a coach to help me navigate business, job, relationships, and life all at once.

  3. Financial health → Side-hustle grew to the point that I was able to save more money. My largest client at the time gave me a full-time job offer that was a 15% raise from my previous job, so I saved that money as well.

  4. Relationships health → Began to date my boyfriend (we’re still together!)

  5. Emergency fuck → Used to focus on stabilization / working with my coach to balance everything I was doing in life. 


  1. Physical health → Kept my level of fitness and health throughout the whole year. 

  2. Mental health → Leveraged my confidence to go full-time on my business, upgrading it from a side hustle.

  3. Financial health → I had the savings to weather the few low months after leaving my job (when my business income hadn’t reached my previous job level).

  4. Relationships health → Continued being in a relationship. 

  5. Emergency fuck → Used to build my business up from side hustle to full-time.


Updating the Fucks 

More moments and little ‘collisions’ began happening in 2018 and 2019. I began to tweak a few action items when they either didn’t feel good or became redundant because the actions had become habit. 

In general, here’s how I tweaked action items: 

  • I tended to wait a month before making any changes unless something felt really off. 

  • Changes were based on:

    • Gut feeling

    • If experience suggested that doing that action item wasn’t me living like I cared about the things I said I did. 

    • If doing the action felt alright but didn’t seem to produce any noticeable progress (feeling or actual) toward my Fuck definitions.

Similarly, I updated definitions as I felt they were necessary, but the only one that changed consistently was my relationships fuck, which followed this path: Grow and help others grow → Be vulnerable and let others in → Love and be loved.

2020 and what’s next

I tried three additional things in 2020 to expand the whole system. Now it’s not just My 5 Fucks, but what I broadly call the Fucks System. 

What worked: 

  1. Identifying 3 life-long altruistic goals. 

  2. Identifying what I want to celebrate having accomplished at the end of 2020. 

  3. Breaking out the 5 fucks categories into 12 “Life Fucks,” following the same system of category, definition, action items but spending more time thinking about what I want to guide me for my whole life, not just a year or two at a time. 

Here’s how the Fucks System looks now: 

  • Whole life:

    • Life Fucks (12 categories)

    • Life-long goals (3 big ones)

  • Annual / Biannual

    • My 5 Fucks

    • “What are we celebrating on new years even this year?”

Now I have a much more holistic system guiding me, and I spend my time ensuring that each piece is connected to one another. But looking back, I can’t believe how much changed since 2017.

Are you interested in reading more about the Life Fucks, Life Goals, and the What Are We Celebrating tactics? Leave a comment to let me know! 

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