Our Most Challenging Choice: 6 Steps to Ensure You Don’t Pick the Wrong Path

Our Most Challenging Choice: 6 Steps to Ensure You Don’t Pick the Wrong Path

Avoid walking the wrong path

“Pursue some path, however narrow and crooked, in which you can walk with love and reverence.” – Henry David Thoreau

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The Choice that Challenges Us All

I spent Sunday afternoon with a couple dozen amazing people at a Live Your Legend Meetup in Montreal. Halfway through the event I believe it was Claire who asked a question I get constantly. Alexey asked it again at our SF meetup last night…

How do you know which passion, interest or idea to pursue and what do you do if there’s not just one thing that excites you? And what if I chose the wrong one?!

If you feel that way, congrats. You’re like most everyone else (me included). The good news is you have options. The challenge is that exciting options and fear of missing out can paralyze us from doing anything at all. We feel like we’ll pick the wrong path so we don’t choose one at all. As a result, progress never happens.

The Wandering (and Endless) Path of Discovery…

Claire asked if I’d had an “aha moment“. A time when I became crystal clear that Live Your Legend would be my focus.

The simple answer is no. For me (and for most), the aha comes in a much more subtle form.

The more obvious sobering moment for me was when I became convinced that the way I was spending my time and career was not who I was, nor was it doing anything worthwhile for me or those around me. Thankfully, that realization comes easy for most.

That wake up is what sent me exploring. All my discoveries came after, not before. And they continue to – most every day. They started as a little extra reading and a new conversation here and there, and eventually they turned into a business and way of life.

So for those of you feeling stuck in picking a direction or wondering what to do next, here are a few practices that can help give you the confidence to keep walking (or get started in the first place), and get you a bit more comfortable with the adventure…

1. Slowly do more of what feels right.

A few years ago it would have been impossible to tell you Live Your Legend would become what it is today. I could have never dreamed we’d be having meetups around the world and that our focus would slowly refine from simply finding and doing work you love, to also surrounding yourself with the community that makes it possible.

I didn’t have a clue about the specifics. How could I? I’d yet to explore them.

And that’s just it – no one does at first. So stop putting so much pressure on yourself to know exactly what it is right now. That’s not going to happen. Even if you think you know, two years from now it’s guaranteed to look different than you thought. That’s the fun part!

All you might know is that you want to do something meaningful (and stop wasting your life) – that you want to help people and you have an idea of some things you enjoy doing, that you might even be good at.

That’s all you need to start. And the way I see it, it’s really the only way to start.

In the beginning all I knew was that I had a lot of fun helping friends make career transitions. So I did more of that. At first that just meant having lunch with people who wanted help. It wasn’t even close to my main thing. I had a full-time job working with some friends at a preventive health startup (which I actually really enjoyed). But I made the time because it felt worth it – and it made me feel whole. The more I noticed and enjoyed the impact, the more attention I gave it.

Be aware of what you enjoy doing and the things you enjoy helping others with. Notice the things that might seem interesting. Slowly start to spend more of your time that way. Start with an extra 10-30 minutes a week. Grow from there.

You can only make discoveries if you begin walking the path.

2. Shadow someone.

I never build a product or course unless I’m confident there’s a market for it. That means I do everything I can to interact with our community and learn your biggest challenges, so I know exactly what to create that will provide you all with the most benefit. That’s the only reason Live Off Your Passion or How to Connect with Anyone exist. Sounds simple, but for some reason it still doesn’t get practiced as much as you’d think.

I believe pursuing a new job, career or business should be treated the same way: test the market. Find a way to be confident you’ll enjoy the work before you dive head first into it. Another reason why step #1 is so important.

Before huge leaps, get a feel for where you’re headed. The easiest way is to take a walk along side someone (or multiple people) already wearing the shoes you think you want. Interested in teaching yoga? Befriend your local teacher or find a friend in the business. Start by taking a few more classes, then maybe attend a weekend retreat and seek out a conference. Maybe even get a side job as the receptionist so you can see the not so glamorous side of things. You want to get a look at all the angles and ideally from more than one person and perspective. Most people are happy to share their experience from the inside. But they won’t share it without you asking. Same goes for becoming a surgeon or starting a tech company. Immerse yourself in the life these people lead.

Don’t compare your insides to other people’s outsides.

This traps us all at some point. We love to look at the glamorous side of someone’s life or career. But what about the rest? How does their husband feel about it? What’s the balance like? Realize you’ll never see even close to the full picture if you don’t get out and learn. Enlist people to help you read between the lines.

Better to spend a few days or weeks in their shoes than to waste months (or much longer) getting a certification, or building something you never really wanted in the first place.

3. Create creative overlaps.

Still having trouble picking a direction? Who says you have to pick just one?! Blending can be a lot more fun. In fact, some of the most unique and differentiated products and businesses come from overlapping a few passions. On Sunday, Olena – another LYLer from Montreal, was telling me about her experience as a professional ballet dancer as well as the degree she had in multiple learning modalities, as well as the MBA she just finished up. Think of the combo she could put together. Talk about standing out!

As for Live Your Legend, there are thousands of sites about passion and finding work you love. But I also happen to be obsessed with meeting, understanding and connecting with new people. And as it turns out, your surroundings are crucial to making any meaningful progress. So I’ve made community and connecting a core part of our foundation and our Passionate Work Framework (better explained in my TEDx Talk). That lead us to creating our flagship How to Connect with Anyone course & community (which we’ll be opening again to a small group in a couple months). Overlapping these two interests has taken LYL’s impact to a totally new level. You’ll also notice I sprinkle fitness and exercise into many of my stories – another huge interest of mine.

The more creative the overlaps, the more interesting the path. And the more likely others will pay attention!

4. Find your model.

This takes walking in someone’s shoes to a whole new level and is best for once you’ve decided on your path(s), but can also help with the deciding. To attempt anything without a model is silly. Be it running 30 miles or launching a knitting business, we need to find the people currently doing the things we dream of doing. And not just any person – but the ones we respect, admire and who have done a damn good job. Ideally this is someone you can befriend personally but that’s not a requirement. With blogs, TED talks, books and every other avenue for learning about someone’s success (or failure), you no longer need to know them first hand.

Study everything you can from their life – deconstruct how they did it, what they specifically avoided and the kind of person they’ve become as a result. The key is to understand the life they lived to get where they currently are, not the public life they lead now that they’re at the top of their game.

No matter what you’re interested in doing, there’s a model who’s already done it, or done something close enough to be worth learning from. Finding the right model will change everything. It’s a process all to itself. I wrote more about it here: On Modeling the Impossible and How to Do Anything.

5. Embrace the Grit.

Avoid the sugar coating. The pursuit of work that matters takes serious…well, work. The peaks and valleys are often extreme and stacked back-to-back. Every step is not bliss. Not even close. Even today I don’t spend every moment doing exactly what I want to do, and getting started was an altogether different story. But there’s meaning in all of it when you know it’s going towards a dream worth pursuing. That makes even the grunt work worth doing well.

And that’s the nature of building something, especially in the beginning. We have to learn new things, experience them and feel the pain here and there. But that’s part of what makes it matter. That might mean working part time as a barrista to make ends meet or moving back in with your parents or a roommate for a few months (both of which I’ve done), who knows. Just don’t lose site of the real vision. The process is where the excitement is anyway.

University of Pennsylvania researcher Angela Lee Duckworth calls this “Grit” – the perseverance and passion for long-term goals and vision. And her studies have found it to be one of the top predictors of meaningful long-term achievement. Her TED Talk on The Key To Success gives a great intro.

Remember, it’s impossible to fail if you refuse to give up.

6. Revel in leaving some stones unturned – for now.

I used to fear leaving one interest so that I could pursue another. Until I realized the only way to have a chance at doing all the things I wanted to do, was to start by doing just one. Leaving a few stones unturned leaves some possibility for later. You can always uncover or incorporate them further down the path – just as connecting and health have become core to our movement here.

As it turns out, you never actually get there anyway. The only real goal is to do what excites you right now. And then tomorrow do what excites you right then. That is surely going to change over time. I certainly know it will for me and it already has since I first started Live Your Legend. And that’s the point. That’s the invigorating part!

You have no idea where it’s going to lead, but if you’re committed to spending your time doing what interests you, that’s a life well lived.

The path never ends

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The Endless Winding Path towards a Dream – in Action…

Claire first asked her question (of which path to choose) to my wife before she posed it to me. Chelsea’s answer was simple and perfect…

“You don’t have to have a crystal clear vision, as long as you don’t give up.”

Chelsea quit her job in corporate PR about five years ago. She didn’t know exactly what she wanted to do but she knew it wasn’t desk jockeying with a phone glued to her ear. She knew she loved health and fitness and somehow that was going to be a part of the impact she made. So she quit.

She got her yoga certification and began to teach. She noticed she felt at home running group classes. She also became a personal trainer, but quickly realized the one-on-one atmosphere wasn’t where she thrived, so she continued exploring. She also applied and was accepted to do a Masters in Public Health, but thought an expensive degree in an unknown field wasn’t the best way to answer her big questions, so she decided to turn it down. The real-life education continues…

She even worked as a waitress on Sunday nights to help with cash flow. She then found The Dailey Method and quickly fell in love with their combo of ballet barre, yoga, alignment and conditioning. She got to know the founder and the managers, and noticed the admiration she had for the work they did – she wanted some of what they had. A spark was lit, so she got her certification and began to teach.

Today she works along-side the founder, trains the studio owners and teachers, and co-manages the studios. Oh and along the way she created her mostly-vegan recipe blog, Food-Life Balance, to round out her love for food.

This all happened over four years. 

She could not have better scripted her dream job. Yet she had no idea what it looked like the day she quit or even a couple years ago. She just continued to follow the path, pursuing what was interesting and learning how to help people in ways that made her happy.

If she would have waited to know exactly where she was going, she’d still be pushing papers in a cube.

If you asked her if it was hard, she’d say “yes.”

If you asked her if it was scary, she’d say “absolutely.”

If you asked her if it was worth it, she’d say “no question.”

Steve Jobs put it perfectly…

“You can’t connect the dots looking forward you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well worn path.”

But the dots can’t connect unless you begin walking the path. It’s the walking that makes it all possible.

Stop worrying about whether you’ll get there, or where there really is.

It’s endless. And that’s the best part of all.

Here’s to wandering with intention,


For the comments: What’s your biggest challenge keeping you from choosing a path? Your answers will dictate our future articles! (email readers please leave a comment here)