What Most Entrepreneurs Never Share: 7 Honest, Actionable Answers to Your 7 Most Debilitating Fears & Challenges

It's not an adventure until something goes wrong Yvon Chouinard

What Most Entrepreneurs Never Share: 7 Honest, Actionable Answers to Your 7 Most Debilitating Fears & Challenges

“It’s not an adventure until something goes wrong.”

– Yvon Chouinard, Founder of Patagonia

Urgent Note: Live Your Legend RAW, our latest creation, went live a couple days ago. You have 2.5 more days (until this Sunday at midnight PST) to get early Insider’s (and very discounted) lifetime access + a live mentoring call with me. Lots more details below, or if you’re a member of our free LYL community, check your email for access.


The Fun of Things Going Wrong…

The above is a snapshot of Chelsea learning to drive a stick shift on a wide open road in Northern Argentina a few days ago. Usually I do the driving in foreign countries, especially when a stick shift is involved, but I managed to leave my driver’s license at a bike shop in Uruguay a couple weeks ago, and despite endless attempts by me and our Argentinian friends, I don’t think I’m ever going to see it again.

That road might look tame enough for learning stick, and it was, right up until it turned to dirt, rocks, mud and river crossings a few miles later – which have become the ‘normal’ driving conditions for the past few days and 10+ hours on the road.  #saygoodbyetopavement #lovemywife

And that is why the above quote from Yvon Chouinard might be my favorite quote of all.

The best stuff is never planned, and if you knew what was coming, you’d likely never start. 

Life (and business) have a funny way of working like that.

And that is exactly why I created Live Your Legend RAW – to share the behind-the-scenes stuff that most entrepreneurs are too scared to share.

It’s a window into the “inner circle” so to speak – of what it takes to live your own legend.

More specifically, it’s a resource for honest, uncut, weekly lessons, guidance & focused actions on how to successfully pursue a dream & do work you love.

Despite some incredible (read: laughable) technological challenges of running a web-based business in rural Argentina (Yvon’s words strike again), LYL RAW went live two days ago (3 weeks behind schedule).

And I’m effing pumped that many of you have already joined!

In building RAW, I asked all of you what your biggest questions and challenges were in pursuing work you love and surrounding yourself with the people who make it possible.

That’s what I always do before creating something new for our community – so I know exactly what would help you the most.

Almost immediately, we had nearly 1,000 responses.

And after reading through them, we found a few things that everyone seems to be struggling with.

This used to surprise me. Now I expect it – it turns out, regardless of what we’re all trying to build, change or improve, or where we are in the process, the same challenge always seem to come up.

So, in honor that, I want to share some brief answers to your biggest questions and challenges.

Over the coming months, we’ll dive incredibly deep into these (and a ton more) in our weekly RAW sessions and lessons.

Honest, Actionable Solutions to Your 7 Biggest Challenges

#1.“What the heck am I supposed to do? I have so many interests and no idea how to choose. How do I find a dream big enough to inspire me?”

AKA: Choosing & Defining a Passion & Dream Worth Fighting (& Living) For

Actionable Answer: 

Follow the path of excitement – follow the spark. No one ever totally figures this out. I’m learning more about it every day (hence creating LYL RAW). And that’s the fun part. Stop putting so much damn pressure on yourself to find that ONE THING.

It’s not about what you’re ‘supposed’ to do. It’s about what you’re meant to do. That passion and fire comes from doing the things that intersect with your talents, strengths, values, beliefs and how you can actually make someone else’s life better. Everything you do – every success or failure, is part of the grand experiment. It’s a data point to better direct you towards the work you can’t not do. You just have to pay attention and do something with it.

Think about what makes you incredibly angry to talk about – something wrong about the world that you can’t stop thinking about. Focus your energy on helping with a solution. And start on an incredibly small scale.

Don’t worry about picking the ‘right’ passion or direction among all your interests. There will always likely be more than you can handle at any one time – and the list will only grow as you continue to pursue what lights you up.

The only way to have a chance at doing it all, is to pick ONE thing right now and move forward with it. The irony is that when you give incredible focus to one of your interests, that often opens up doors to incorporate others.

A few years ago I was terrified to launch a site that was only about doing work you love. There was so much other stuff I wanted to talk about. But now that incredible focus has allowed me to incorporate social dynamics, human connection, relationships, entrepreneurship, physical fitness and a lot of adventure (as I write you from a tiny town in Northern Argentina).

But if I started with all those things, most of you probably would have never heard of LYL. There would have been no clear and specific reason to pay attention.

#2. “I have no idea where to start and can’t find the motivation & momentum to keep going. How do I create a business without having it all figured out first? What’s the very, very first step?”

AKA: Starting (& Finishing) Your Most Important Projects & Finding the Unshakable Courage to Pursue Your Dreams

Actionable Answer:

No one has it all figured out. No one. And anyone who says they do is a liar. If fact, the more you learn and figure out, the more you realize you have to learn and figure out. But that’s part of the party that is pursuing a dream, doing work you love and making a difference in the world.

All that matters is the next step. If you can take that, then you can take the next. That’s what makes magic. Stop spinning your tires trying to figure out how to build the whole damn castle. Find a good plot of dirt and a couple good bricks. Make the steps so incredibly small that they’d be impossible not to take.

And in case you’re wondering what to specifically do first or next, it’s the thing that scares you the most. And the thing that’s likely to help others the most. It’s not getting business cards or a new suit or even your website URL.

It’s getting out in front of people and finding a way to change their life. That is all of our biggest task. Figure out how to use your talents, strengths and passions to make one person’s life better. Then do it with another, and another. Only after you’ve nailed that, do you think of how to apply tools and technology to scale your impact. Almost everyone gets this backwards (I know I did). Nail your impact first, then scale.

And if you’re lacking motivation, start spending time with other people with similar dreams. That’s why we created our free LYL Local communities. None of this is meant to do alone. Be grateful for the fact that you’re even able to read this and have the ideas that you do. Then realize that it’s your ultimate responsibility to do something with it!

#3. “How do I start something that makes real money, on-the-side, so I don’t have to take all the risk of dropping everything. I just can’t just check out and take all that financial risk right now!”

AKA: Building a Risk-Averse Passion-Based Business On The Side

Actionable Answer:

No one can just drop everything and leave. And even if you could, it’s often not the smartest thing to do.

Create your side hustle first. Build out your idea on the side, and use your current gig as a learning ground, as you test out what you love, how you can help people and what is going to actually work.

Live Your Legend was a side project for over five years before I went full time. And by then I was sure it was going to work, because it already had. The community was growing, the revenue was growing and I clearly found a way I could change peoples’ lives.

I cannot stress this enough – do not quit tomorrow with no idea of what’s next. There are so few people that can thrive in an uncertain environment like that, that I’m now just telling everyone to wait. If you jump ship without having a clear idea of what you actually want to be doing, the uncertainty will likely cause panic, which will lead you to another miserable job – and another 6-12 months of wasted time. Nothing’s worse than that.

If you figure out how to add massive value to someone’s life, then you can find a way to build a successful business around it. That first step is the hard part. Then you can find models of people who have successfully built the businesses and lives that you want. Study them like crazy.

The incredible thing about being alive today, is that we rarely need to invent something from scratch – the business models and examples are everywhere. We just have to figure out how to apply our ‘thing’ to them.

Start with making your first dollar from adding meaningful value to someone’s life. If you can make $1 from that, you can make a lot more.

#4. “How do I meet people who actually support me pursuing these ‘crazy’ dreams of mine. My friends and family don’t get it.”

AKA: Finding YOUR People Who Refuse to Let You Fail

Actionable Answer:

Start with one person who inspires you. A family member, a friend, a friend of a friend. Anyone who is somehow linked to you or someone you know. Reach out to them, tell them what you admire about them and what you’d like to build. Start by spending a few minutes on the phone or an hour out on a workout together.

At the same time, spend one less hour with the people who drain your energy. We all know who they are. Make a list of your toxic friends and slowly spend less time with them as you spend more time with people who inspire you.

Then join a Live Your Legend LOCAL group (or start one) in your home town. We now have them in over 300 cities in 70+ countries. They are 100% free and are full of ‘crazy’ people who believe what you believe. People just like you and me.

Tell the people closest to you what your goals and dreams are and why. Sit them down 1:1 and tell them how much you love and care about them and how you believe your plans will make you a better person – and improve your relationship with them. Make it crystal clear that you are not asking them to change. Show compassion.

Then spend another hour hanging around someone who inspires you. Then another. And another. Life’s too short to spend time with people who kill your dreams.

#5. “I feel guilty charging others for giving my advice, especially knowing there are other people better than I am at what I’m offering.”

AKA: Making Your First Dollar & Becoming a Practical Expert

Actionable Answer:

There will ALWAYS be people better than you. No matter how hard you work. That’s not the point.

The point is to find the intersection of your unique talents, passion and experience +the people who desperately want and need help with what you know. That is what it means to be a practical expert. And that is all you need to help people in a massive way and build an awesome business around it.

If you wait until you’re the leading expert in the world, you’ll never get anywhere. The world’s greatest experts earned those titles by doing things long before they were as qualified as they are today.

The only qualification, credential and definition of expertise that matters is getting massive results for people. You can start doing that in some capacity right this second.

And believe it or not, people will value and appreciate you more if you offer an honest and congruent way for them to compensate you. When people receive massive value, they want to pay for it. And if they do, then they’re much more likely to actually value and implement what you teach them.

Every person that’s been on this earth for a couple decades or more, has some talent or experience that another group of people is dying for help on. Those people would happily pay you for your services – and thank you for it.

That starts by finding one person. By changing one life. That will give you the confidence to start charging for the value you’re providing.

Most of the time the only thing keeping you making money from your talents and passions is…YOU. You’ll probably start making money as soon as you decide to start putting a price on what you’ve got to give.

Don’t overthink this.

#6. “How do I get people to even pay attention? Where do I find them and what should I be doing to build that online following?”

AKA: Building a Loyal & Raving Audience

Actionable Answer:

First start with one person – in the real world. See above – you noticing a pattern here? Then use those in-person interactions to craft a very specific and concise description of how you’re helping people (i.e. your personal positioning statement). For LYL this is ‘how to find and do work you love and surround yourself with the people who make it possible.

Then create a platform (a website or blog with just one or two pages to start) and create incredibly useful and directly actionable content to help the people you want to help. Put your absolute best stuff out there.

Then create incredibly useful content for other websites with similar and bigger audiences. This is what many call “guest posting.” Do this as far and wide as possible. Start with small sites, build credibility, then ladder up to bigger sites.

Then point those readers to a specific page on your site that gives huge value and asks them to join your community (i.e. subscribe to email list). Like we do at liveyourlegend.net/toolkit. Sending them to a specific page will literally increase your conversion rate by 5-20x. No joke. It’s incredible.

The formula is simple: Create massively useful content for you tribe + create massively useful content for other tribes. Repeat a lot of times.

Then continue to blow your audience’s mind with value.

#7. “How do I know which areas of my business to focus on when? What’s the ideal 80/20 time management breakdown?”

AKA: The Best Daily Habits, Tools & Routines for Handling Stress, Pressure, Fear & Rejection

Actionable Answer:

Let’s keep this one dead simple.

Do your most important task right when you wake up – the one that scares you the most. You know what’s most important or at least one of the most important things. Don’t do any other work until this is done. Then the rest of the day will be a victory no matter what.

Put all your creative energy into how to help people with the things you’re good at and enjoy. Be relentless with this. Turn off all your BS notifications for emails, Facebook and all else. Install Freedom or RescueTime or something similar to block websites. Or better yet, don’t turn on the Internet (disconnect wi-fi) until you’ve done what matters.

And give your body and mind first priority. You can’t operate at full potential if you miss workouts, eat like shite, rush non-stop through everything and leave no time for yourself and those you love. This is not optional. Taking care of yourself is more important than any of the other stuff.

Your body fuels your mind and they both fuel your potential. 





Slow down.

Know Enough to Take the Next Step…

I know these answers barely scratch the surface, and that’s the point.

Because knowing enough to take the next step is all you ever need – and usually all you should realistically expect to find. As much as you want it all laid out, with perfect clarity, before taking the first steps – that’s just not how it works.

That’s not how anything meaningful comes to life.

Start with the dream and vision of the world you want to live in.

Then take the most educated next step possible – TODAY, right this second. 

Know that all of it is going to evolve as you blaze the trail. Welcome the adventure. Because that’s what makes it worthwhile (and so much damn fun).

Especially if we get to all do it together.

That’s why we’ve created Live Your Legend RAW.

And I cannot wait to see what you do with it.

Ciao from Tilcara, Argentina…


P.S. Our first RAW Session, going live next week, is: “The Single Habit that Turns Your Idea into a Profitable Business”

Only 2 days left to save 36% ($86) on lifetime access and get in on the live mentoring session with me to cover your biggest roadblocks.

If you’re a member of our free LYL community, check your email for access details.