4 Delicate Questions to Ask Yourself Before You Start Anything New

Whether you’re a ‘Jumper’ or a ‘Toe-Dipper’, you still need to know whether you’re ready or not.

Kunal Walia
Jul 29 · 6 min read

When it comes to how we approach new adventures in life, we typically fit into one of two personality types.

First, we have the “try-before-you-buy” sort, henceforth referred to as “Toe-Dippers”.

Toe-Dippers like to tread carefully. They think they need a plan before they get started. But with an excessive amount of time spent on ‘pros vs. cons’ lists, they also lack conviction when they finally decide to press “go”.

At the other end of the spectrum, we have the super-excited, always-enthused type that say “yes” to just about everything. Let’s call them “Jumpers”.

At first glance, Jumpers come across as positive, and their energy is infectious. But they often risk getting carried away — think: throwing $10,000 on a brand new home DJ studio, only to later find they’re averse to loud noises.

In an ideal world, the best decisions and outcomes would arise by taking the underlying enthusiasm of a Jumper with the tactical focus of a Toe-Dipper to create a “Toe-Jumper” (clever, right?)

So how do we reach such a state?

For starters, we need to tread carefully around the pitfalls that each personality type brings to the table when it comes to planning their next adventure. Let’s see how.

#1. What’s Your “Why?”

“He who has a why to live for can bear almost any how.” ― Friedrich Nietzsche

Behind every decision lies a purpose, often disguised under layers of reasoning. Allow me to explain.

Suppose you wish to lose 20 lbs to get in better shape. ‘Improving your health’ is your first level of reasoning.

Beyond this, there’s another fundamental reason why you’re signing up for Zumba classes. You wish to increase the chances of living longer to be there for your kids and grandkids. Now we’ve reached your purpose, or your why.

Keeping this in the back of your mind is crucial.

By skipping over this first step in the process, as Jumpers so often do, you risk falling into a slump when faced with your first hurdle.

But Toe-Dippers are also guilty of misinterpreting this process. They often spend too much time planning what they’re going to, and not enough time considering why they want to do it.

Takeaway #1: Know your “why” before you begin. It will help you down the road.

#2. Are You Fine With Not Seeing Immediate Results?

We live in a world where we’re used to instant gratification — most of our desires are at our doorstep (think: one-day delivery).

As such, we’re guilty of carrying this mentality wherever we go. We become desperate with the idea of seeing immediate signs of success when we’ve only just begun.

We, as 21st century humans, need to accept the idea of going unnoticed when we try something new.

Said differently, you have to write 100 articles before your 101st goes viral. You have to win 10 small customers before you gain the recognition of a large one.

As James Clear states in his bestseller ‘Atomic Habits’ (which I highly recommend),

“We often dismiss small changes because they don’t seem to matter very much in the moment.”

Now, Toe-Dippers are comfortable with the very idea of not seeing immediate results — they’re still in the trial phase, mentally at least, which itself can be problematic, as we’ll next see.

Jumpers, on the other hand, struggle immensely with an absence of results. They wrongly assume the energy they put into their latest pursuit should pay-off immediately. Unfortunately, it doesn’t work like that.

Takeaway #2: Jumper or Toe-Dipper aside, patience is a must if you’re determined to reach your goals.

#3. After How Long Will You Upgrade?

Let’s say you’ve discovered a passion for photography.

If you’re a Jumper, you’ll start by purchasing a top-of-the-range digital camera. Oh, and let’s not forget about the tripod, a fresh set of enhanced lens, and of course, LED lighting equipment for those portrait shots.

As you might have guessed, Jumpers risk wasting money if they later discover their interests lie elsewhere.

Toe-Dippers are different. They’ll prefer to click away on their iPhones, often overlooking the fact that it’s been 2 years since they first started.

And by forgetting to reward themselves with more advanced kit, Toe-Dippers risk waking up and feeling like that they haven’t progressed much. At some point, they might even decide to quit.

The easy solution is to find a sensible compromise. Start with the basics, upgrade later. But importantly, define what “later” means to you.

Is it a case of time — e.g. “after 6 months, I will buy a new camera”, or perhaps it’s based around a certain milestone — e.g. “after my 100th blog post, I’ll buy a new laptop”.

Either way, give yourself the freedom to try as many hobbies as you’d like, but for as little cost as appears sensible.

Takeaway #3: Find the right time to upgrade. It will help sustain what it means to progress.

#4. Is Quitting A Viable Option?

“The thing that is really hard, and really amazing, is giving up on being perfect and beginning the work of becoming yourself.” — Anna Quindlen

This might sound controversial, but throwing in the towel can often be the wisest move you make — even if you’ve figured out everything described above.

Let’s say you’re determined to learn how to sing. But after a while, you slowly realise you can’t stand the sound of your singing voice. You gave it a go, but it’s safe to say your time is better spent elsewhere. What you set out to achieve wasn’t the right fit. Perhaps you’re better off learning the piano instead.

Now Toe-Dippers, by their very nature, give themselves the liberty to move on if they lose interest. But they often abuse this liberty. They haven’t decided that quitting is an option, they’ve assumed it is. As a result, they risk giving up when they should persevere.

Jumpers, however, will continue to persevere with activities they despise. Why? Because they went in too hard initially. They never came to terms with the idea that their latest pursuit might not be suitable.

Whether you decide to go all-in or keep an exit option in your back-pocket, ultimately comes down to what feels right to you.

But know this, you’ll always later find yourself in a pickle if you’re never honest with yourself from the outset.

Takeaway #4: Answer this truthfully: ‘Are you in it for the long-haul or not?’

In Summary

Having an awareness of whether you’re a natural Jumper or Toe-Dipper is a wonderful starting point to understanding how you’re most likely to respond to the idea of a new adventure.

But if you really want to make better life decisions, it’s far more important to consider whether you’re truly ready to embark on your latest pursuit, regardless of whether you’ve always been a Jumper or a Toe-Dipper. Here are 4 questions to ask yourself:

  1. Have I understood my “Why”?
  2. Am I okay with not seeing any immediate signs of success?
  3. Am I crystal-clear on when I will upgrade?
  4. Have I come to terms with whether quitting is a viable option for me?

If you’ve answered “no” to all of the above, then it might be time to head back to the drawing board. Doing so can be highly advantageous in the long run.

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Kunal Walia

Written by

27. Finance nerd by day. Writer by night. Dreamer at all times. Finding new ways to learn. Sharing more ways to grow. E-mail: kunalwalia.medium@gmail.com

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join 119,000+ others making the climb on one of the fastest-growing pubs on Medium.

Kunal Walia

Written by

27. Finance nerd by day. Writer by night. Dreamer at all times. Finding new ways to learn. Sharing more ways to grow. E-mail: kunalwalia.medium@gmail.com

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join 119,000+ others making the climb on one of the fastest-growing pubs on Medium.

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