How to Find the Guts to Take a Leap

April 7, 2011 · 44 comments

I bet, after reading that headline, you know what leap I’m talking about, what “leap” means for you.

Chances are, if you’re reading this blog, you’re looking for the guts to throw yourself into your writing or take a career break to travel. Or maybe you want to change jobs or move to a new city or start your own business or have a family.

Dogon Country, Mali

I feel like the money belt I'm wearing in this photo kind of ruins it. But it's better than an iStock photo of a random guy in a tie leaping into a white background, right? (Dogon Country, Mali)

I’m talking about The Big Leaps. Not asking out the guy who’s always making everyone laugh at the geeky tech meet-up you attend every month. (Oh wait, is that just me?) Or mustering the courage to try a new kickboxing class at the gym. Those moves can be scary, no doubt. But this post is about The Big Leaps, the ones that are scary because they have the potential to be life-changing.

Making a decision to take a life-changing leap often comes down to just that — making the decision. Committing to the leap. But there are certain things you can do to make it less scary. I say this because I was scared to all hell of quitting my job to travel. (Well, my colleagues called it quitting; I called it leaving.) Taking a long, solo backpacking trip was something I’d wanted to do for years, but I kept waiting for the right time. I waited until I finished my master’s degree. Until I got my first job in newspapers. Until I had three years of work experience on my resume.

Then, finally, I made it happen. I like to think that for my next leap in life, I won’t wait as long.

“Taking a leap” sounds spontaneous. But the truth is, many of the people who inspire us with their leaps prepare for months or even years to make it happen.

So whatever your dream is — whether you’re halfway there or haven’t even started — here are some tangible steps you can take to propel yourself toward that starting line:

Tell your friends. Saying your dream aloud makes it real. It helps you commit not only to the idea, but to making it happen. And if you’ve surrounded yourself with the right people, they’ll hold you to it. They’ll help you follow through — make sure you follow through — because they love you, and they want you to be happy.

Surround yourself with people who support your dreams. This is easier said than done, because even the nicest people in your life might look at you like you have four heads when you tell them you want to open a bookstore or take more than a week off work to travel or live a television-free life. Some people won’t understand these choices, because it never occurred to them that these options were choices at all, and it doesn’t seem fair that you could do those things if they can’t. (They can, of course; they just don’t realize it.) As Chris Guillebeau says, “realistic” is the adjective of cynics.

But all you need is a few people who understand your pursuits, a few people who encourage you without that twinge of resentment in their voice, a few friends who are figuring out how to live their lives in their own out-of-the-box ways. These friends will sustain you, and you’ll become closer for it.

Lay the groundwork. What stands between you and this dream? Even if you can’t bring yourself to decide on a launch date, figuring out what you need to do to make it happen will help you see the leap as an attainable goal, rather than an overwhelming mess of what-ifs. Laying the groundwork also helps you prod yourself toward making your adventure happen.

When I was a reporter at the Houston Chronicle, I knew I wanted to take a backpacking trip, and I knew I wanted to hit some French-speaking countries, but I didn’t know when or how that would happen. Though I had no concrete plans, I signed up for French classes, figuring the longer I had to brush up on the language, the better. I didn’t plan it this way, but in retrospect, going to those classes helped my dream come into focus. The more comfortable I felt with my French, the more I envisioned myself taking my trip. And learning a language, like saving money, isn’t something you can do overnight. Start on tasks like this now, so when you’re mentally and logistically ready to make your leap, you can.

It's harder to turn back when your pack's already in the boat. (Toliara, Madagascar)

Make a check-list. In addition to those big tasks like saving money or learning a skill, you’ll face lots of little tasks that will have to get done before taking your leap. Some will have to wait until the last minute, until you know your plan and your time line. But you can get started on others now. Want to climb a mountain? Start getting in shape. Looking to make a career change? Focus on growing your network. Making a check-list of all the things you need to do — both big and small — will make it less overwhelming. Try to check something off each week or month so you can see how you’re working toward your goal.

Save money. I love Ask A Manager’s post about what she learned from quitting her job during the recession because she says having savings helps us act from strength, not desperation. It’s not just the money we need, it’s the feeling of security. Feeling secure financially helps us take leaps in life. One way to save money is to live more simply.

Look for ways to make more money. This is option No. 2 when it comes to saving. Rather than skimping to put aside a buck here or a buck there, be creative about ways to bring in income in addition to your day job. Because of the Internet, this is easier and cheaper to do than ever before.

Start getting rid of stuff. It’s far easier to wrap your head around leaving a place if you don’t have to take a huge moving van of stuff with you. It’s even easier to jump into a new venture or take on a new responsibility that doesn’t require moving if your physical life feels less cluttered. Give away things you don’t use or need, rather than piling them higher and higher in the attic.

Remind yourself that it may never be the “right time.” I’m all about laying the groundwork and making your own luck, but the truth is that it’s never the perfect time to take a leap. In retrospect, it always is. It’s so easy to say afterward, “I was ready for a move and all the pieces fell into place.” But while you were making the decisions to take that less-traveled road, the pieces likely felt more disjointed. And when we’re scared, it’s easy to use one challenge or obstacle as an excuse, as the piece that won’t fall into place. Find another place for it, or put the puzzle together without that piece.

This is where you might have to be creative. How can you travel when you have a mortgage? How can you write a book when your spouse thinks it’s a bad idea? How can you take your leap when all the logistics of life and money and family stand in your way? Think outside the box. If you want it badly enough, you can find a way to make it happen.

Connect with people who have done what you want to do. No matter how unique your upcoming adventure, someone else has probably done it. And thanks to the blogosphere, you can probably read about it. Find blogs on the topic, and connect with those people on social media. Ask them how they overcame the obstacles that are holding you back. Chances are they feel strongly about the choices they’ve made, appreciate that you value the lifestyle and want to help you. Learn from their mistakes.

Let yourself dream. Because once you’ve started laying the groundwork, it’s no longer just a dream. You’re turning this into reality. Pat yourself on the back, and let that dream grow.

Take some chances. Taking risks does not feel good in the gut, nor does it always turn out how we’d hoped. But it turns out well enough that it’s worth doing. And the truth is that no matter how much you prepare for your leap and set the groundwork and make your own luck, it’s still going to feel like a risk. And you still have the potential to fail — depending, of course, on your definition of failure. I probably don’t need to remind the awesome readers of this blog that a new experience can never truly be a failure, because you gained that: a new experience. Maybe your launch won’t go as smoothly as you’d hoped, but I bet you, in nine times out of ten, you won’t regret it.

Have you taken a leap lately? If not, what leap are you waiting to take? How can you make it attainable?

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{ 31 comments… read them below or add one }

Lisa McKay April 7, 2011 at 8:44 am

Great post. Yeah, I took a leap. I said yes a couple of years ago when Mike shocked the life out of me by proposing after we’d spent exactly twenty days in the same country. And now look where I am. Barefoot and pregnant in the tropics and (mostly but not always) loving it. Best leap ever!
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Alexis Grant April 7, 2011 at 9:14 am

Aw, this made me SMILE this morning!

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Sarah April 7, 2011 at 9:23 am

Alexis, I loved this post. Taking a big leap seems incredibly big and scary, so I loved how you broke it down into small, measurable, and somewhat easy to do steps. I was wondering: how did you decide what “leap” you wanted to take? Sometimes I feel like I have a thousand things swirling in my head about “leaps” I am interested in taking. How did you narrow down your goal and realize what it is you truly wanted to do?

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Alexis Grant April 7, 2011 at 9:50 am

Hm. This is a question I haven’t been asked before! I had a broad idea of what I wanted my “leap” to be, but I think getting started on the planning early helped it come into focus more. For example, I knew I wanted to take a long-haul trip, but I never planned to focus on Africa — that happened organically as I did little things to put my plan in place.

If you’re not sure what your leap should be, try letting yourself dream a little. When friends tell me they don’t know what kind of job they want, I sometimes ask: If you could do anything, what would it be? Sometimes we limit our choices without realizing it by unconsciously crossing off options that don’t seem as “realistic” or may be difficult to attain. So I’d start with that, by asking yourself what you’d do if you could do ANYTHING. And move forward from there.

Does that help at all?

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Sarah April 7, 2011 at 1:43 pm

Yes! This helps a lot. I am so guilty of not letting myself dream because I always think, “oh, I could not possibly do that!” And the other piece is, like you said, I need to own what it is I want to do instead of hiding it.

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Heather Rae April 7, 2011 at 9:38 am

I love this post, Alexis. Mostly because I think I needed this little reminder. My life has taken some unexpected turns these past few months, and a lot of the things I thought I wanted have changed. But there are some big leaps I still want to take – like traveling out of the country for an extended period of time. I need to start moving on the planning phase. :)
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Alexis Grant April 7, 2011 at 9:52 am

This made me think a lot — your note about how things you thought you wanted have changed. I’d love to hear more about this! I think it’s important to let ourselves let go of dreams that change as we grow older — but that’s also why I try to accomplish some of my dreams when the desire hits, because I know it might not last long. (Like traveling in an uncomfortable bush taxi — Seems to get less appealing the older we get!)

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Doug Mack April 7, 2011 at 9:54 am

Great advice here! Piggybacking on the comment about telling friends, I’d add: tell everyone. I mean, within limits–not the random person sitting next to you on the bus. But you never know if that colleague or friend-of-a-friend will have good advice or a helpful connection. AND I always find that the burden of having the entire world *thinking* I’m going to do something makes me get out there and do it, if only so people who don’t really know me–in fact, know only that I’ve been planning this adventure, and therefore use it as their conversation-starter–will stop asking, “Hey, did you ever do that Semi-Crazy Thing you’ve been yammering about?”
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Ami April 7, 2011 at 10:27 am

Oh, Alexis! This came at the perfect time. I made the big leap to leave a relationship that wasn’t working last May, and now I’m preparing for the big leap to full-time freelance and part-time yoga teaching. These are great tips that I’ve used this year and plan to keep using as I make the shift toward working for myself.
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Alexis Grant April 7, 2011 at 10:57 am

Ami — I’ve loved reading on your blog about your leap OUT of a relationship and INTO yoga. But I didn’t know about the full-time freelancing! Wow, you are really going for it! So happy for you! I hope you’ll keep us posted on how it goes… And what kind of support/help you need.

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Andrea James April 7, 2011 at 12:33 pm

Thank you for this post. You really got me thinking about some things and about what I want my next leap to be.

And thank you for the shout out in one of your links up there! :)

When I hear the word leap, I think of a game I played with myself as a kid.

I would take one of the bars off of my swingset so that I had a clear span of swingset bar that I could jump and catch on to. It looked like this, only imagine that middle line at the top. /—–\

And I put a wooden bench perpendicular to the bar, very close, and reach out and grab the bar. And swing there.

Then, I’d move the bench back a couple of inches. And I’d jump a little and grab the bar. Let go, drop down, move the bench back a few more inches, jump again, catch the bar, let go, drop down, move the bench back.

I kept doing that until I could no longer leap and grasp the bar.

I always impressed myself because I would get the bench more than a full body length away from the swingset — and I made it!

And once, I started the game by putting the bench far away. But my heart would pound and I would be too scared. And I couldn’t catch the bar. I knew I had to start easy, to prepare, to work my way up.
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SoVeryVienna April 7, 2011 at 12:40 pm

Right on. I agree with and am trying to do several of these tactics. Like right now, I’m cleaning out my house. Big undertaking, but I already feel better. We need less stuff in this crazy world of excess.

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Rory Moulton April 7, 2011 at 5:35 pm

You’re right – there’s never a perfect time.
I’m working on my third leap. The first two just sorta came about and couldn’t have been more worthwhile. In fact, I’m the person I am today because I’ve taken the leap x2.
Brilliant post. Excellent read.
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Becky Benson-Flannery April 8, 2011 at 8:24 am

Thank you for the encouragement! I could not read this until this morning, but saw the post’s title in my inbox yesterday and carried those words with me throughout the day. Maybe your title pushed me or my mind finally focused; either way my gobbledygook writing morphed into my next project yesterday–I feel great about it.

I agree with you that telling your friends helps to propel you. I use this strategy with exercise as well. If someone knows I plan to run, he will likely ask me about it later and my pride will not allow me to disappoint! We often forget how supportive friends and family are…

Lastly, I found myself traveling alone (so scary!) through Europe and it was the best experience–I met more people I would not have met had I been with other people and I was far more focused on my surroundings.

Often what is most scary and challenging rewards us the most!!

Thank you!
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Alexis Grant April 8, 2011 at 10:33 am

Hi Becky — What a great note! Thanks. You’re right that life’s challenges can turn out to be the most rewarding. Psyched to hear your next project is in the works! Keep us posted.

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Kathleen Pooler April 8, 2011 at 1:02 pm

Alexis,

Wonderful post and very timely for me as I transition (I don’t like the word reirement!) from my nursing career to fulltime writing. Thanks for sharing so many practical tips from your own experience. Change is never easy and taking that “big leap” can be scary, but ,I agree, if we want to follow our dreams,we have to be willing to take that plunge. Thanks for the reminders.

Kathy
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Emma April 8, 2011 at 1:09 pm

Great post! I am so glad I took a career break to travel, and now one of my good friends is embarking on a trip around the world this month. I’ve been sending her links to your blog as she prepares for her trip!

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Lindsey O'Connor April 8, 2011 at 9:14 pm

You, dear Lexi, are an inspiration.
Blog on. Your posts matter. They inspire.

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Kim May 15, 2011 at 11:00 pm

I just found your blog and I’m so glad I did! I’m also a writer and a soon-to-be long-term traveler. I’ll be quitting my job in about eight months or so for at least a year of travel (the leap) and plan to spend the time building my blog and expanding my writing career. Anyway, this is all great advice. Everything I do these days leads me in the direction of my goal. Taking the leap takes months of preparation but it is so.totally.worth.it.

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Mark September 19, 2011 at 2:18 pm

There is just one thing I would add to all of this talk of “making a leap”. You need a back up plan if all these carefully planned ideas fail. I took a leap 7 years ago to go back into my design business. Friends and family said ” Don’t do it” but I went ahead. I used the Earl Nightingail/Napolean Hill philosophy of burn all bridges and sink all ships so there is no chance of retreat. It was the old “No retreat, failure is not an option” mantra. It was a disaster. The Great Rescission hit along with other factors I ended up having to go back to those family and friends who said I was crazy and ask for help just to stay off the street. I am just now recovering from all this financial disaster and moving forward. I had no back up plan. I would say it doesn’t mean you give up on your dreams but an important slogan in all this is “Live to fight another Day”. If you have a back up plan you can retreat,regroup and try it again.

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Alexis Grant September 19, 2011 at 3:03 pm

Hi Mark — This is SUCH a good point, so thanks for chiming in. I need to make this point more often — That you should be prepared and have a back-up.

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Christina Wood December 23, 2011 at 1:15 am

I’m definitely new to the blogging world. I was an English major in undergrad and I’ve always loved writing and reading. But I also have a passion for education as well. So far I have been having a hard time finding a way to blend the two until now. For the past few weeks I have really thrown myself into my blog and into networking to bring more awareness about my blog. I’m at a point where I’m pretty sure that I want to go farther with this and perhaps start doing some free-lance work in the future. But I know I have sooo much to learn. So I definitely agree with your tip to connect with those who have done what I want to do. I’ve been reading blogs like crazy and I’m soaking up everything so that hopefully my blog can be half of what yours is. :-) Keep the tips coming!

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Anne Belov February 12, 2012 at 4:25 pm

I made my leap 24 years ago last month and have never looked back. (mostly, anyway) I was more pushed than actually jumping, but I had been preparing for several years prior to the leap. I won’t say it’s easy, but overall I have done better than if I had stayed in my menial unpaid job.

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Steve G April 6, 2012 at 7:02 am

Making any kind of dramatic change in our lives can be daunting. As you have described though, if this is well thought through and for the right reasons, then it is likely that chasing a dream will motivate us and inspire us to live our life to the full. Changing career can be one of those big leaps in our lives, but I think having the courage to do this is always better than staying in an unhappy or unfulfiling job.

Steve invites you to take a look at this post on Change of Career

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Rekaya Gibson April 8, 2012 at 12:20 am

Though I am not there yet, reading this post is right on time. Thanks for sharing your experience.

Cheers!

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Kate May 18, 2012 at 2:28 pm

Hey thanks for sharing your blog. Im in a very difficult place right now and and battling those fears and doubts. My family have all grown and live lives of there own. I live alone and rent a house i can barely afford, just running my house takes all of my wages, i am in a very physically demanding job that i hate. I have no money left to enjoy life and just work and sleep. I want to give it all up and travel, maybe get a campervan and travel europe, work to get by etc, i want to absorb different cultures and environments, im 46 and fear if i dont do it soon it will be too late for me. Any advice please?

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Fran August 13, 2012 at 7:56 am

I’m on the path to fulfilling my dreams but even when you determine what dream you want to fulfill there are times where you question how it’s being fulfilled and need to open yourself to other possibilities. I also always try to have a plan b in case things start to fall apart with the original plan and that way you still get it accomplished.

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Suzi September 16, 2012 at 6:09 pm

Funny to read this today; just this morning I was having the debate in my head about watching TV. It does take up so much time, yet is entertaining, and at times educational, and just good company.

I’m not convinced I can give it up 100%, but I made a deal with myself to not turn it on until 7:00 PM, when my eyes are burned out on my computer screen and my writing begins to turn into babbling. TV provides an escape from the day and a place for my brain to run on low speed.
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cb February 2, 2013 at 4:13 am

I am still not sure which leap to take, of my 2 options, but thank to your GREAT article, I’ve made lists for both, laid some groundwork ideas, and now I’m going to go out and start doing small check lists of things that both options require. yay! this helps. thank you so much!

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Brenda April 10, 2013 at 6:22 pm

Hi. I really want to leave my dead end job at the Department of Social Services, leave a cruel husband, and move to a new city and start over again. There have been so many changes on my job that there is very little “social” left of Social Services. Everything is automated & now running like a production office. My husband is mean, lies on a regular basis, cheats, and is very cruel and uncaring. I can handle infidelity but its the mental cruelty that’s breaking my spirit. I am 43 years old and I’ve been with him since I was 15 and there are times when he goes for days & says nothing to me. I need to move because in-spite of his cruelty I have loved this man for 28 years so I don’t think I can handle living in the same town with him if we separate. But we own our home-no mortgage and I would be giving that up if I leave. Also I have Vitiligo that’s spreading like a wildfire so I’m skeptical about finding a new job. Plus in order to take this leap I would have to use my retirement money & I’m afraid if the money runs out before I find a job. We have two children together, one starts college in the Fall he’s 17 & our daughter is 11. But he could care less about either one of them or me for that matter if we move.

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Stacy Brown April 12, 2013 at 10:08 am

Thanks for this post! I recently made the “leap” with some career changes, and am now struggling with it not going as expected (not just that it is harder work than I wanted, :) but that I’m not so sure where I actually want to end up when I land from the leap). So, I’m just going to consider myself still mid-leap, think outside the box, spend lots of energy truly evaluating what I want, and keep plotting my course to get there. (Yes, I know I am mixing metaphors like crazy) The exciting/terrifying thing for me is I can sense that something is brewing…..big and amazing changes are still coming from this leap and I’m doing my best to find that balance of preparing for it versus just going with the flow and watching for signposts along the way. Thanks for your inspiration and your organized ways of breaking it down!

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