Knowing when to take The Jump

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this blog post is part of a series, #oneblogpostaday.

the first part of this series is focused on purpose + career.


The Jump looks different for everyone.

For some, it’s leaving a job that’s sucking your soul dry. For others, it’s diving into that side hustle that’s been on your mind for months. And heck - it could even be deciding to move to a brand new city.

Whatever The Jump is in relation to - it can be difficult to figure out when you should actually do it. And how to muster the confidence to freakin’ go for it.

Oddly enough, I’ve made The Jump many times in my (short) career so far - from finance to philanthropy, from New York to California, from big corporate job to being an entrepreneur. And trust me - looking back on all of them, they were actually amazing…once you get over the pseudo-scariness.

So, here are some of the questions I’ve asked myself (and others) when they’re thinking about making The Jump:


1. What is it you actually want to do?

A lot of times when people are on the edge of The Jump, they say they have absolutely no clue what they want to do. They’re super confused. The only thing they know is what they don’t want to do.

You know what I’m talking about, right? Maybe you’ve been there before (or are there right now).

…but, when you actually let yourself Go There for a second, you know. Deep down, you know. You’ve been dreaming about it for a little while now.

So if you’re feeling confused about what you realllly want to do try this: Imagine yourself in 5 years. What do you look like? Where do you live? What are you doing? What are you wearing? Who are you with?

You could write it down, sit in silence + visualize it, or even speak it out loud to a friend. There’s no pressure here; just go with your gut feeling.

Then take a step back and think about it - how far off is that vision from the decision you’re scared to make?

3. What’s so scary about it?

A lot of times, we build up fear in our heads that don’t actually match what would happen in reality. It’s easy to convince ourselves that something is way more scary than it actually is.

It’s time to get real about the scariness + discomfort. Objectively, what’s scary about making this choice?

Every choice has some level of risk involved. And, depending on what stage we’re at in our lives, our risk appetite varies (this is cause of how many inhibitory brain cells we have, or our “traffic cops” as neurologists like to call them).

So, take a moment to get out of your brain and away from your traffic cops. Make a non-judgemental, objective list: What would actually be scary about taking This Jump?

2. Why haven’t you done it yet?

So, now that you have a clue as to what you want to do and what the risks might be, it’s time to get real about why the heck you haven’t done it yet.

There’s no judgement in this question at all - sometimes there are real circumstances that prevent you from taking The Jump (student loans, a sick parent).

But sometimes, we hold onto non-issues in our mind and use those to prevent us from taking The Jump. Like, not having the extra cash for an Equinox membership or having to put yourself out there to make friends in a new city.

This question is all about confronting your discomfort. Doing something scary, like taking The Jump, takes a lot of gusto. You have to be your own cheerleader.

So, take some time to get real about why you actually haven’t taken The Jump yet. Journal about it or talk through it with someone you trust.

Hint: usually this is a lightbulb moment.

4. What’s the worst that could happen?

If you’re still feeling conflicted, there’s a really helpful exercise that Tim Ferris came up with called Fear-setting (watch the ted talk here).

Fear-setting is the opposite of what we often do when thinking about making big shifts. Usually, we set goals and think ahead.

But, Tim found himself choosing not to take risks because he was scared. So, he decided to define his fears instead - to show himself that they weren’t as bad as he might have thought (or heck, maybe they were and he shouldn’t do it!).

So, use this template (or make your own!) and write out the worst case scenario for your version of The Jump. What would you do if this worst case scenario actually came true? And, is it truly as bad as you thought it could be?

When I was deciding to move to San Francisco with Dupi, I was pretty scared. I didn’t have a job, friends or a plan. But, when I did this fear-setting exercise, I realized that the literal worst thing that could happen was: I hated it, I didn’t find a job or make friends, and I wanted to come home.

So, the solution was? Come home. Even in the worst case scenario, the outcome was pretty good.


And finally, make a plan (but trust, too)

Oftentimes, we let our fears define us.

We hold ourselves back from doing something, anything, because we’re scared of what could happen. We’re worried about leaving our comfort zone. We don’t actually know what we want to do (or so we think), so we avoid it.

But, all it takes is a little self-reflection. This doesn’t always mean that your answer will be yes - taking the jump tomorrow! Maybe after answering all of these questions you decide that it’s not the right time. Or it’s not as good of an idea as you thought.

Both of those options are a-okay.

But, maybe you go through these exercises and decide that yes! FINALLY! It’s time to take The Jump. That’s cool too - perfect even.

My only caution would be - don’t overplan. This is where fear creeps in again. Sometimes, we just have to trust ourselves and that long-term vision we see. We just have to go for it.

Because, we can plan and plan and plan….but planning doesn’t always get us to the goal. Just go for it.

Katina Mountanos