What’s Holding You Back?

The gap between what we dream of doing and what we manage to do is often so big we can barely see the thing we want on the other side. How do people who live more adventuresome lives make their dreams happen?

They use some very simple, very effective tools.

Adventuresome people aren’t magically born daring. They’ve simply discovered effective tools, including a special arsenal that helps them bust through the biggest obstacle of all: adventure is scary. 

Here are seven of the most widely-used obstacle-busting tools from my book, Gumption: The Practical Woman’s Guide to Living an Adventuresome Life. These tools come from all kinds of otherwise ordinary women who have learned how to dare. You may be surprised at how many of the tools you already use yourself, without being aware of it. The trick is to consciously apply them to the scary thing you want to accomplish.

Tool #1:  Ask yourself what’s the worst that can happen?

I know this seems like the last thing you should do to calm yourself, but it’s my personal favourite boogeyman-buster. Confession: my answer is usually ‘I will end up on the street with all my belongings in a single plastic bag’. Personal history has demonstrated this is extremely unlikely to happen to me, barring a world apocalypse, but it remains my very scary place.

How on earth could that be calming?

By going to the extreme, your rational brain kicks in and declares: that’s ridiculous. Then you back up a bit to a still scary, but more likely, disaster scenario. By then your rational brain, feeling smug from having pooh-poohed disaster idea #1, is fully engaged and figuring out how to overcome the problem. Take advantage of that state of mind to figure out how you would cope with such an outcome.

Write down the potential disaster and your possible coping tactics.

Come back to it a day or two later and you’ll probably have a few more coping ideas that your creative brain has worked out while you went about your daily life, without you even knowing it. The brain is clever like that.

Tool #2:  Embrace Your Screw-ups

Remember the times when you really screwed something up. Geez, you may be thinking, why would I torture myself with that? There is a point: whatever cringe-worthy thing(s) you did, it’s in the past and you’re still alive.

In fact, you probably got some good stuff from it. Stuff like:

  • discoveries about yourself and the world
  • the knowledge of how not to repeat the crappy event
  • what is important to you
  • what is not
  • how to cope with pain
  • how to recover

What a lot of good gadgets you added to your life’s toolbox, just from one goof-up. Write them down, so you can remember that screw-ups often have silver linings.

Tool #3:  Unburden Yourself

Most adventures require at least some logistics in order to make them a reality. We need to get past the idea that logistical challenges are insurmountable obstacles. Very few things are really insurmountable. They might be more effort or cost than they’re worth, based on your priorities. They might take more time than you are actually willing to give them. They might take more sacrifice.

These are all choices we make, not crosses we are forced to bear.

What are you choosing over your adventure? Write down all the things that are taking priority over what you want in your life.

Maybe you’re making the right choice for now, and you really can’t do your daring thing at the moment. But maybe that’s just become a reflex answer that keeps you in a safe – if dull – place. If you want to be more adventuresome in your life, you have to revisit these choices regularly. Like the kid in the backseat who incessantly asks ‘are we there yet?’, at some point, if your adventuresome self keeps asking enough, she will get the answer she wants: ‘Yes!’

What if, once you’ve had a cold, hard look at the things you’ve placed before your adventure, you do decide it really isn’t a good time? Do this: stop kicking yourself for not making it happen. It’s a huge waste of energy. Simply ask yourself: is there anything I can be doing now to move this forward for the future?

And if even that isn’t possible, put the adventure away in a little box and make a note to yourself to bring it out in whatever amount of time seems right, be it 6 months, 6 years or whatever. You could label it The Dream Box. You could get all Martha Stewart with it and gussy it up if that helps you deal with postponement.

Then get on with something smaller you can make happen now. That’ll keep toning your adventure muscle until you’re ready to put it to full use.

Tool #4: Ask an Expert

The Buddhist proverb ‘When the student is ready, the Master appears’ seems to be especially true for adventurers. It’s a really consistent theme among the stories I’ve collected. Your ‘master’ could be a professional, or just somebody who’s been there and done that. Someone who understands the ins and outs of what you’re trying to do, and is willing to help you.

Who could your expert be, or where will you go look for them?

Now, more than ever, it’s easy to find an expert. Google just about anything and you’ll get the opinion of someone who’s done it. Toss a question out on your Facebook or LinkedIn page. You don’t even have to know someone personally. If your big adventure involves going to the moon, it might be a little more challenging to find the right people to question. For most other things, it’s a snap.

Advice about backpacking through Kazakhstan? It’s there. About letting your hair go grey? Yup. Ditching your partner, changing your profession, cycling across the country, having babies without men? Ditto. This is the single most effective – and easy – way to get the real skinny on your supposed obstacles.

Tool #5: Ask Yourself

It’s not easy to dive into uncharted waters, especially if you’re a person who’s used to being on top of things. Who wants to feel incompetent? Women seem to have a special penchant for Imposter Syndrome. You know, that’s when you’re doing whatever you do and you think: at some point people are going to discover I don’t know everything about this.

Well of course you don’t. Who can, when circumstances are always different and we can only carry our experience from one situation to another and hope it’s helpful?

This applies to adventures, too. Instead of thinking I don’t know how to do that, think about what you’ve done that was similar, and understand that you do have experience you can use to make this new thing happen – successfully.

You already have things that you can do. Let them enlighten your ‘can’t do’s’. Say, for example, you want to travel alone to do the Iditarod Dog Sled race. Start with what you can do: yes, I’ve traveled before, even if it was with my sister to Florida; yes, I’ve been outdoors in the cold for long periods before, even if it was only for cross-country skiing; yes, I’ve owned a dog and was able to train it to sit and come. And so on.

All the skills in the above example would be useful for the Iditarod. They are insufficient without the help of more experienced people to teach you the rest of what you’d need to know. But you would not be starting from zero. Not at all.

What skills and experience do you already have that would be useful to your adventure? You know what to do: write it down. Never dismiss your existing experience as insignificant to the task ahead. Everything builds on everything else.

Tool # 6: Call in Your Friends

Well duh, right? Of course you’re going to use your pals to help get your gumption up for your adventure. But here’s the challenge: you have to choose the right ones.

Some will blindly tell you there’s nothing to worry about because you’re great, talented, capable etc. Cheerleading can be powerful, but personally I get more buzzed from proof points than from hopelessly biased, loving enthusiasm.

Some will be great critical thinkers who will help you figure out what you really need to do to get the job done. Super useful, but before you talk to these people make sure you’re thick-skinned enough, or determined enough, to take that kind of hard-boiled practicality on board without having it backfire and scare you even more.

Some will actually, actively, crush your dream because they fear either what might happen to you, or what might change in your relationship if you go and get daring on them. They probably won’t even realize they’re doing this. When you’re young and it’s your parents trying to do the crushing it can often be just the ticket for getting you to act, just to prove them wrong. But when it’s your BFF, not so much.

Ask yourself: who among your potential cheerleaders are the best support for your needs and frame of mind?

It’s OK to be choosy. You don’t have to leave somebody special out in the cold; just don’t expect adventure-support from them. Not everyone is going to be made for that.

Tool #7: Grab a Partner

If the fit is right, a partner can be invaluable in an adventure. You egg each other on, share the risk, share the hours that need to be spent, share the joy, share the memories. And often balance each other’s shortcomings, especially in business partnerships where one person can’t be expert on everything.

While there are also many adventures that crave going solo, the right partner can sometimes be the final, enabling part of the puzzle that turns ‘maybe’ into ‘let’s go’.

It’s also very comforting to have a hand to hold while diving into the deep end.

Ask yourself: Would your adventure be better with a partner, or is it something you need to do solo?

If you think a partner would be useful, why?

  • What do you need them to do?
  • What do you have to offer on your side?
  • What kind of character do they need to have to partner with you in this adventure?
  • Do you already know someone who could fit the bill, or do you need to meet them? If you need to meet them, how could you do that?

There you have it: seven tactics you can use right now to get unstuck and get on with your dreams. Seven is a lucky number in many cultures and I like to embrace superstition when it’s encouraging. Whatever moves us forward!



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