7 Steps to Begin & Master Your New Radical Path
How to break free from default choices and create a life entirely your own
We’re not all wired to love the default menu of options until we retire or die. Even if one path is exciting or useful for awhile, it can become unbearable to imagine decades more of the same ol’ same ol’.
Yet, when we consider what else might be possible, we hit a brick wall.
At 38, I’ve had more than 25 intentional life changes. There is nothing I’m likely to do the same way forever. When one path stops being what I want, I embrace the change — no matter what that change requires. I keep chasing my excitement & curiosities. And I thrive on being new.
This year, I quit my 9-5 to become a full-time adventurer and writer. I live on a small sailboat with my husband & cat, which we rebuilt ourselves. We have limited cash. I had no clue about sailing just months ago. But none of that matters. We’ve now started a years-long adventure of sailing around the world.
I’m an expert at mastering new beginnings of all shapes & sizes. I can identify the need to change before a current path gets too tedious or causes too much pain. Then, I can intentionally redesign my life in ways that lead to enormous success according to my metrics.
I’ve moved abroad, lived in 5 different states, got sober, climbed out of egregious debt, became an A+ student after nearly failing out of high school, earned a full ride to Harvard to study a topic I knew nothing about just years earlier, and then left my hard-earned career for a life at sea.
I know I have 25 more changes on the horizon — just for the intrigue of it all.
That’s all a radical path is about: seeing more of what’s possible for ourselves during our finite time on this planet.
I promise you: curiosity is the only requirement to begin. Then, you only need to follow a handful of steps.
And within a few months or a year, you can do whatever the f*ck you want.
Here’s how.
1. Identify your needs and explore your magnetic curiosities
Most people who are struggling in a current path know it. They feel it when they tell someone “Everything’s great!” Their brains present jealousy, anxiety, or inferiority when they see someone experiencing bliss.
I know this because I’ve felt this way too.
It’s challenging to admit that we’re unhappy with the foundational decisions we’ve made. But that’s only because many of us believe that change is impossible.
Our brains are lying.
We can make bold decisions to change our lives at any time we please.
At least twice per year, I ask myself a simple question:
“Is this even the life I want?”
If I answer “No,” and then start to come up with a bunch of reasons why it’s not my fault, I stop right there. It’s a giant step forward to acknowledge that I’m not living the life I want. I can work with that. I just don’t listen to whatever denial, confusion, or projection comes next. I know that’s keeping me from change.
I’ve answered No to this question now so many times that it doesn’t produce the same anxiety it used to. Now, I feel a sense of excitement because I can take a radical path to fix it.
There’s hope.
If you also answer this question “No,” and then come up with reasons that detract from this single illuminating truth, either do what I do or think very carefully about whatever justifications come next. And don’t wallow in them. It’s hard to admit you’re not stoked about decisions you’ve made in the past. But it’s much easier when you know you can do something about it.
After you decide you aren’t living the life you want, then you can look at a solution.
You do this by asking yourself two bold questions:
What do I need in my life?
What’s a practical plan to make that happen?
I promise it’s not as scary as it sounds.
Get wild and crazy.
Journal.
Talk to a friend and therapist.
Our needs can be broad or specific. They only need to be honest. They can be “a more interesting life!” or “a master’s degree in opera.” Or “quitting my career to sail around the world.” It’s whatever lights you up the most.
Then, when you understand your needs, look at what other people have done. The internet is filled with people who have found solutions that might work for you. Look at YouTube, Instagram, or Substack. Focus on the stories that aren’t super polished & glamorous. Cling to people who clearly have the same principles as you. Look for those who will truthfully address your questions and concerns and help you see a path forward.
I promise that your role models, mentors, and future heroes are out there and they’re probably willing to chat with you.
Then, you start to figure out how you can do it in a way that works for you.
This is how I realized I could pursue my exciting, curiosity-inducing, imposible-sounding needs. But I just needed the beginning of a practical plan.
It’s how I knew I needed to come out of the closet and found role models to show me how.
It’s how I knew I needed to live overseas and figured out the visa process and other logistics.
It’s how I knew I needed to get sober and learned there was hope.
It’s how I knew I needed the best education possible and discovered a path to get a PhD with no extra debt.
It’s how I knew I needed a stimulating career that aligned with my principles and metrics of success, and figured out where to look.
It’s how I knew I needed to understand the U.S. and the world for myself and found a way to overcome all my distorted perceptions & fears.
Last year, my husband and I realized we weren’t living the life we wanted and then answered these questions in collaboration (What do WE need? What is a practical plan to make this happen for US?).
If I were single, I wouldn’t have chosen sailing. I would’ve probably become a digital nomad in Thailand. Something more straightforward.
If we had kids, maybe we would’ve chosen to move off the grid somewhere and learn as a family to become independent and self-reliant.
But sailing was the perfect combination of both of our needs, curiosities, and complementary strengths. Thankfully, my husband shares my principles of adventure, passion, freedom, and more. And he’s super handy with tools. So, after looking at our options, we gelled on sailing really strongly. Then, we decided to do it.
If you think that your partner isn’t game for your vision, or there are some other real constraints (with money, family, or something else), then there may be a middle-ground compromise.
Maybe it’s not taking on more student loan debt to change your career, but it’s taking an online bootcamp from an expert with demonstrated results.
Maybe it’s not traveling full-time, but it’s living in new places for 1-year stretches.
Maybe it’s not living on an artist commune, but it’s starting a makeshift art center and hosting inspiring people in your home for extended periods.
It’s challenging to redirect the ship. There’s so much momentum going in the default direction. There are so many unknowns.
But tell me, what other choice do you have?
It may take months or a couple years to get something off the ground. But that’s OK. It’s better than waiting decades until you retire or it’s too late.
This is why I ask myself early & often whether I’m living the life I want. It gives me a chance to course correct early, if needed, given it’s usually not like flipping a switch.
If it feels like a lot, that’s also OK.
Take a week and think about these questions.
And you can always drop me a line.
2. If one other person in the world has done it, it’s possible for you, too
You can redesign your life around whatever lights you up the most. Read that again. I promise you this.
I guarantee you that someone who is less skilled, less hard working, and with fewer resources has figured out how to get what you need most.
This is where the role models, mentors, and future heroes you identified earlier will pay dividends.
These people show us what’s possible — at minimum.
If you want to become a world-famous pianist at 75 years old, come up with a practical plan and go for it.
When we bought a sailboat last year, we had little experience and limited cash. We didn’t personally know anyone who had a sailboat. We didn’t know how to fix it up. We didn’t think we could afford to sail indefinitely. We didn’t know how to sail on the open seas. We didn’t know the logistics of living in such a small space without a refrigerator, washing machine, and mailing address.
But we knew we could do it because others had done it before us.
It took 1 year of preparation, including coming up with a practical plan, getting the boat ready, and saving more cash. Then, we got on the water full-time.
We still wonder, “Is it possible for us to sail around the world?”
But of course we can.
We know this because others have done it who are less skilled, less hard working, and have fewer resources.
All you need is to imagine with every fiber of your spirit what might be possible and understand that you can become that new version of yourself.
This is the attitude that you need to have when you’re taking a new radical path.
And you must believe you’ll figure it out, too.
The documentary Ice Blink followed the Martins, a family of 5, who lived on a sailboat not much bigger than the one we bought, and they spent nearly 10 years exploring the Arctic. People told them they were “crazy” and “stupid,” and what they were doing was “impossible,” but that didn’t sway their goals. They made it work, even though they weren’t rich. The dad, Dave, would clean toilets and work on boats for cash in the places they sailed. He ended up becoming a freelance writer & photographer (people wanted to tag along on the adventure) to help fund the trip. Dave would say, you just need to believe you can do it.
Their story helped give me the courage that I could reach my writing and sailing dreams, too (but with no kids — only our cat, Pineapple).
I learned this lesson years earlier.
When I was in community college, I first said out loud, “I’m going to go to Harvard.” My classmates and instructors probably thought I was delusional. But I truly believed, “Other people go to Harvard, so that means I can, too.” Of course, I worked relentlessly toward that goal. I got great grades, did all the extracurriculars I could, and earned strong letters of recommendation. Then, I applied. And I got in.
The point is that nothing is off limits, especially if other people do it.
Maybe there’s never been anyone who has done it with your specific challenges.
But that still shouldn’t stop you.
My husband and I still recognize that we’re uniquely different than the folks who came before us in the sailing world. We’re a same-sex couple. We have histories of substance abuse. We don’t have pensions (or trust funds). We’re not expert sailors. We’re not totally fearless.
But this is the equipment we got.
What other choice do we have but to figure it out, too?
When you’re ready, you can do whatever the f*ck you want — especially if it’s already been done.
3. Restructure your life 100% around that new thing
Dan Koe recently said:
“Most people are pouring their time, energy, and money down the drain…. They will look back years from now (that's a lie… many people never self-reflect) and realize that even though they feel tired and near burnout, they've accomplished nothing meaningful.”
This has been me at various points, so I know it’s true.
But for people who are uninspired by ordinary paths, there’s a risk we’ll regret not pouring all our precious resources, including our time & attention, toward getting on a new track.
There’s a huge opportunity cost to staying distracted.
Just 1 year ago, I had temporarily convinced myself I was stuck and couldn’t take any more radical paths. Even after all my experiences, the doubt snuck in. I briefly thought I had too many bills, my job was too good to give up, and I’d probably be a government bureaucrat forever.
I thought maybe we could move onto a sailboat, someday, but maybe when we retired.
Then I woke up.
I realized that I felt stuck because I didn’t spend any time figuring out my new needs over time. I was pouring my most precious assets down the drain. Each day, I handed them over to my tedious career, scrolling on my phone, and stressing for 3-4 hours per day over the news. And that was a huge reason I felt like I had nothing left.
When I realized my real goals were writing and sailing, and I recognized these distractions were preventing me from taking my new radical paths, I made pretty simple tweaks. I started waking up 2 hours earlier and changed my work schedule so I could focus my most creative morning hours on my writing. I got off of social media and I kicked my obsessive news consumption habit.
I suddenly had time for Substack, planning our move near the ocean, and figuring out how we’d get an old sailboat on the water.
In just 1 year, I clawed back nearly 1,500 hours to invest in intentionally changing my life — even while I was still working my 9-5. Read that again. That’s more than 8 months of 40-hour workweeks in one year that I could focus on my real goals just from changing small habits.
Then I put all those extra resources into identifying my needs, making that practical plan, and redirecting the ship.
If you want to take a new radical path, you’ll need to throw everything at it.
Ask yourself:
If you knew it was possible to achieve your exciting, curiosity-inducing, impossible-sounding goals — would redesigning your life even be a sacrifice?
My husband and I would also give up our house, say bye to all our friends and family in Colorado, and move to a rural coastal town 1000s of miles away in North Carolina.
This was how we’d afford the refit for the sailboat, continue to save money before I quit my job, and work on the boat for as long as it took. But it was so exciting. We were making moves toward our new radical path. We spent nearly a year giving it everything before we got the boat on the water. And it was the best feeling ever.
Whatever. It. Takes.
That’s the trick.
We knew our lives could be more fulfilling and no one else would do it for us.
Maybe there’s a more moderate way to do this, to dip one foot in the water, but I’ve never had any luck with that. I would give up after not seeing enough progress or get distracted with something else.
In my >25 radical paths, I’ve always dove in with both feet.
Plus, the benefit of reorienting our lives completely around a new goal is that it makes it very hard to back out.
I can’t tell you how many times we had enormous setbacks and we’ve said, “But we already bought the damn sailboat!”
The decision had already been made.
And sitting here in my beautiful floating home in Annapolis Harbor, 100s of miles from where we started, I’m so grateful for that fact.
This is why it’s so critical to figure out what we need and then hold onto that information like it’s the truest thing about the universe.
You’re building a new foundation around what will lead to the best life imaginable for you. This is the most important endeavor you may ever take and it deserves your full body, mind, and spirit.
We sometimes make slow progress, but the time is going to pass regardless. One year from now, you can either be a year closer to your goal or lose a year because you didn’t get started yet.
Is there anything else more meaningful?
4. Never fear looking like an idiot
The hardest part about being new at something is that pesky brain again. It’s our egos. And it despises not knowing what it’s doing.
But we’re not all raised to know how to do new sh*t.
We’re prepared for the ordinary paths and then choose from the default menu of options. That’s what our societies and education are pushing us to do: become materialistic, distracted, and average.
The vast majority of our family, neighbors, coworkers, and friends are doing the thing in which we want to break free.
There is only one way to learn — from the ground up.
We have to find our role models elsewhere. Or we need to be our own role model.
That’s why it’s called a radical path.
It makes perfect sense that we don’t know how to start finding more passion in our careers even if it’s for less money, or becoming a full-time nomad, or relocating to a farming commune, or opening a surfing school in Central America, or getting our pilot’s license, or living in a tiny home like a van or yurt, or building a new solopreneur empire with just our laptops, or voluntarily simplifying our lives and embracing minimalism.
It’s uncommon.
But a radical path is about figuring out what’s possible, and I guarantee you it’s possible to learn anything.
It will be uncomfortable at first, but that’s part of the journey. Laugh through it. Even those awkward laughs work.
Over time, you’ll learn what you need to know. All those questions you have right now, or the vocabulary you don’t understand, or the endless concepts you mix up, or the skills you still need to learn — it’ll all be crystal clear in a few weeks or months. Then, you’ll have more questions or need to learn more skills but you’ll have confidence you can do it. This is how an expert is born.
When I started my new sailing life, I’d often talk to sailors referring to parts of the boat that sounded like they had misspoke. Even the second time I heard it, I didn’t know what it was.
Clew? Vang? Danforth? HUH?
But I didn’t let that stop me. Now I would pass the sailing vocabulary test. I can sail decently and manage the galley like an intermediate-level chef. I did all this with no formal training or prior experience. And I’m so frickin’ proud of myself.
Again, it’s all part of seeing what’s possible for ourselves.
When I went to Harvard as a bright-eyed biology PhD student, I felt like an idiot every single day. My ego writhed in pain. I felt like I was living in the shadow of my classmates and professors who were much smarter. I thought I didn’t belong there. But then my advisor told me, “When you embrace feeling like an idiot, and accept that it’s not a bad thing to feel dumb — that it’s just an opportunity to learn — you’ll really start to enjoy yourself.”
He was right, I did start to love it, and it changed how I’ve treated every new radical path since.
When I say devote 100%, I mean your ego, too. Check that at the door. It’s much more fun that way anyhow.
5. Don’t let anyone or anything stop you
One of the best decisions I ever made in my life was not going to college right after high school. My parents and former classmates were confused. But I actually swore off college forever. I hated sitting in a classroom and being told what to focus on. My curiosities were about the real world and exploring on my own terms. So that’s what I did.
Instead of college, I saved up all the cash I could and moved to Australia by myself at 19. I only had $2,000 left after I paid for the plane ticket, visa, and backpack. But my visa allowed me to work, so I didn’t let that relatively low number affect my decision. I’d figure it out.
My parents freaked out.
My friends & coworkers probably thought I was nuts.
But I didn’t care.
I knew that I needed a life of adventure, passion, and freedom. I had a practical plan. So, I went.
And though it was hard, it was the best thing I ever did.
When we know we need to take a radical path, there are 100 hurdles that can stand in our way if we let them.
Where do I start?
How do I figure out the paperwork?
What if my partner thinks I’m crazy?
What about the dog or kids?
What will my family, friends, and coworkers think?
But if you think it’s your partner, family, colleagues, kids, or pets that are holding you back, I bet it’s not true. I can list the dozens of totally normal people who overcame these perceived hurdles and moved abroad, explored the world indefinitely, lived on a small sailboat, homeschooled their kids, brought their pets, and are living their fantasies.
You just haven’t decided yet that you can begin & master your radical path.
“Unless one is unconcerned by other people’s judgments, has no fear of being disliked by other people, and pays the cost that one might never be recognized, one will never be able to follow through in one’s own way of living. That is to say, one will not be able to be free.”
-The Courage to Be Disliked by Ichiro Kishimi & Fumitake Koga
When people delay or decide not to take their new radical path, it’s often because they have a single hurdle that is holding them up.
But if that’s the case for you, that’s amazing. It’s likely not the showstopper that you think it is. And when you find the solution to that one thing, it helps you build courage to conquer the next. And that’s where confidence comes from.
Once you take your radical path — even if your family, friends, or coworkers doubted your decision before — either (1) they now recognize your success and are so happy for you, or (2) who cares?
Before we decided to give everything up and move onto a tiny sailboat, we had 1,000 doubts & obstacles.
How do you even buy a sailboat?
What will we do for health insurance?
Will people attack us because we’re gay?
What if our parents don’t understand?
What if I burn bridges when I tell my boss & coworkers?
Do we have enough money to even get started?
What will be do about money when we’re on the sailboat?
And so on.
It’s normal to have doubts. It’s abnormal to overcome those doubts.
But again, that’s why it’s a radical path.
It’s all about embracing the excitement & curiosity and seeing what’s possible if you do it anyway.
We overcome the hurdles and setbacks, then we earn the satisfaction of having figured it out. Then, the hurdles become fewer and the setbacks insignificant.
And you begin to learn that you truly can do whatever the f*ck you want.
6. Embrace strategic frugality
Money is usually required to make a big change. It may be a little or a lot. But if you’re like me, you don’t have infinite amounts. You don’t have some rich benefactor to write you a check whenever you need it. You need to figure this part out yourself.
But the good news is we only need ENOUGH money — and sometimes minimal money — for the freedom we crave.
I know this part can feel overwhelming, but if egregious debts or lack of cash are the last thing stopping you from your new radical path, I promise you, it’s worth any temporary sacrifice to remedy.
Lack of finances should never stop you from setting your sights on the most exciting, curiosity-inducing, impossible-sounding dream.
I can’t tell you the exact way to do it with your situation, but I can tell you one thing: it’s always possible. But it requires a different way of thinking.
It’s all about strategic frugality.
When I moved back to the U.S. after living in Australia, I was $10,000 in credit card debt. I still can’t believe it. I thought I had no way of paying that off. But I assessed my options and found a solution. I asked my parents for one last favor before I went off and fended for myself forever. I’d move back in with them for 6 months, get 3 jobs, and pay off my debts. But if moving in with my parents wasn’t an option, I would’ve moved in with my grandma, slept on my friend’s floor, or found a stranger’s couch.
Whatever. It. Takes.
I knew that getting out of debt was necessary to have any chance at taking a new radical path anytime soon.
And same with my student loans. I structured my life after grad school in a way that I could get rid of my high-interest student loans ASAP. That meant living in a smaller house, driving an older car, and cooking 95% of meals at home.
I saw debt as the antithesis of freedom.
Our next radical path can be focused on getting out of debt or making money. But it’s with a purpose. It’s to allow us to take the next radical path.
You can follow the same framework outlined above and focus 100% on getting that financial freedom you’ll need for the next big thing.
It may not sound super exciting, but again, ask yourself:
If you knew it was possible to achieve your exciting, curiosity-inducing, impossible-sounding goals — would redesigning your life even be a sacrifice?
When we were rebuilding the sailboat in rural North Carolina, I still worked my 9-5 to fund all this. It was hard, but so worth it. We made a super-detailed budget to figure out how much money we’d need for our adventure, tracked all of our income sources and expenses, and measured our progress each month.
We also made some decisions based on trade offs. For example, we lived in a boring house on a busy highway for $1,200/month instead of paying double to live in the nicer side of town. However, this was an easy call because it would’ve cost nearly $15,000 extra over the course of the year to live in the cool area. And it just forced us to make that boring house a home we liked.
I also paid attention to every dollar I spent. I even stopped drinking my $2.50/day Coke Zero because I knew that was nearly $1,000 over 1 year. And now, I’m stoked that I have that money to put toward a new mainsail.
Now that we’re on the sailboat full-time, we have a financial runway that will allow us to focus 100% on sailing and enjoying the new adventure as we make our way to Latin America over the next year. I have a ton of time & energy to write. We’re only spending $1,000 to $1,500 per month for food, insurance, boat maintenance, and more. We know we can swing this for awhile without an income.
This is all because we made a practical plan to get what we needed and then embraced strategic frugality.
But my needs of “an adventurous life” were also broad enough that I could’ve done something else with much lower costs than sailing, if necessary.
Again, a radical path will look different depending on our situation. And it may involve some middle-ground compromise — especially due to our financial realities. But the point is that it’s possible with some strategic frugality and enough time.
You don’t need $1 million to start a new radical path.
You just need to make the numbers work.
As your coming up with your practical plan to meet your needs, think about every dollar you spend in terms of how it looks over the year. It’s wild to acknowledge that $20 per day is $7,300 over 12 months. When you know how much value you’re sacrificing, buying Starbucks every morning and lunch at work will sound way less appealing.
Just never say “F*ck it” when it comes to spending money. You’re really saying “F*ck it” to your next radical path.
7. Maintain a healthy pace and celebrate your wins
Now you’ve figured out what you need and how to do it. You’ve realized it is possible. You’ve devoted 100% to it. You’ve started to love being a newb. You didn’t let anyone or anything stop you. And you figured out the finances. The last step is building a sustainable path to make sure you don’t drive yourself crazy.
This is critical because there will be so many times when you feel the hurdles or setbacks are insurmountable.
Even though you’ve gotten ruthless about your intentional life change, you’ll need to understand how to take it at a healthy pace and celebrate your progress.
This is where it may be helpful to break your radical path up into phases, while never losing track of your goal.
For example, our goal of sailing around the world is way too big.
So, Phase 1 was the “Getting Started" phase.
For you, this might include research online, chatting with people, trying out what might work, creating a budget, and figuring out more logistics needed to get there.
Phase 2 might be the “Acquiring the Skills” phase or “Making the Move” phase.
And so on.
Our “Getting Started” phase lasted a year.
Now we’re in Phase 2, which is the “Learning to Thrive on the Sailboat” phase. We’re learning how to sail, how to happily live in 100 square feet together, how to roll with the punches from the weather & other harsh realities, and more.
Phase 3 is the “Sustaining at Sea” phase, and it will involve making enough money to pay our bills. But we don’t stress out about that yet because we’re not in that phase. And plus, we’re following the Dave Martin plan: we just need to believe we can make it work :)
It’s possible at times that you’ll get overwhelmed by your exciting, curiosity-inducing, imposible-sounding dream.
Take it slow, if needed. Take 18 months instead of 12. You need to take care of your emotional & social health. You need breaks. You need to maintain a community. You need sleep. You need ice cream.
And you need to celebrate all your wins along the way.
Seriously, it’s amazing even if you just admitted to yourself that you’re not living the life you want. If you’re just thinking about what you need and discovering a practical plan to get it, you’re on the right track. Pat yourself on the back. But keep making that practical plan. Then, you will have just completed Step 1!
Now, every time you continue giving your all each day despite some challenge or hurdle — or notice a huge change in your level of fear, courage, or confidence — these are reasons to celebrate. You’re becoming an expert at your new radical path. You’re going to make it. I promise.
On our sailboat, I’m constantly noticing how much more resilience I’ve gained since starting this adventure. I was so fearful and green when I started out. But I’m not the same person. And I’m so proud of myself.
I treat myself with ice cream.
Now you’re also going to see what’s possible for you during your finite time on this planet.
You’re in for a life of unbelievable surprises.
Your wild dream is waiting just around the corner.
Until next time,
—Cory Vinny
If you enjoyed my article today, please consider buying me a cup o’ Joe.
You can help sustainably power our adventure at sea — and around the world. I’ll continue posting weekly newsletters at sea. Thanks for your support!
I love hearing about how this adventure started. I do find I often question my choices, particularly when stressed (“why on earth did I choose to live in a country where it is dangerous to drive when it RAINS??” etc.) and I expect there will be times you do too. I think what makes the adventure is pushing through the challenges - money, security, social networks - and seeing the other side of that wall. Looking forward to hearing more!
This is an excellent list for those who are looking to make their own radical change. There are things here that I’d never considered when we made our own radical paths (and there’s been more than one!) and these are so empowering.