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Above the Clouds


“Look before you leap” is one of those bits of wisdom that’s been around for centuries.

And for good reason.

It’s designed to keep us safe and caution us against making hasty decisions. The words encourage us to consider the possibilities of what could go wrong should we make some type of bold move.

Obviously, that’s smart, but it also holds much greater potential when we think of it more broadly and apply it to something specific in our own lives. For example, our work.

One of the most beneficial applications of the adage is when a person decides to change jobs or careers. The problem is, few people explore the saying fully, even though it’s at the core of producing happy outcomes.

Let’s look at a few examples that underscore its value.

What Can Happen When You Leap Before You Look

stressed woman

Holly, 58, works at a small nonprofit and has been unhappy at work for months. She wants a job that allows for greater sociability, less responsibility and more relaxed hours.

She was a server in her 20s and 30s and has fond memories of guests she met and her many coworkers. A return to the restaurant industry sounds appealing.

Holly realizes serving requires a great deal of energy and menu knowledge, so she thinks becoming a hostess will be the solution. She submits her letter of resignation and excitedly applies at a few high-end restaurants.

Well, it turns out Holly would have benefited from the pre-leap look. She got caught up in the excitement of doing something new that checked several of her boxes, but she failed to consider what her actual day-to-day experience would entail.

She learned most available hosting shifts would:

  • Be scheduled from 2-10 pm four to five days a week.

  • Require her to be on her feet the entire time.

  • Pay about 20% of what servers average.

Disappointed and deterred, Holly was able to keep her job at the nonprofit and decided to figure out how to be happier there. Unfortunately, that didn’t last long and now she’s quit her job and is back at square one.

How A Comprehensive Look Can Steer Your Leap In The Right Direction

girl at window with coffee

Then there’s Calli. She’s lived in a college town for decades, but family obligations and health conditions prevented her from completing her college degree. Now 52, she’s determined to graduate. Education is always valuable, so her dedication is noble and inspiring for sure.

However, Calli can’t decide what to major in because she has no idea what she wants to do after college. A full exploration of what her ideal workday would encompass — along with her strengths, mission, values, goals, income needs and priorities — will be super helpful.

How A Look Can Lead To A Leap You Love!

man named Pete happy at winery

Finally, there’s Pete’s scenario. At 62, he was ready for a change from his high pressure, accounting-firm life. Making impetuous decisions isn’t part of his methodical personality, so Pete’s change-making process looked like this:

  1. He worked with me and got clear on his why, strengths, top values and the impact he wants to make.

  2. He mapped out his ideal workday.

  3. He explored opportunities that best met the criteria for 1 and 2 and is now exceptionally happy as a manager of a small winery.

Looking To Leap? Do This.

legs of woman leaping on boardwalk

Looking before you leap is one of the most powerful steps you can take when it comes to decisions about whether or not leap — and if so where — professionally.

It’s goes beyond making a decision that aligns with your goals or purpose, which of course are really important, too. It adds an element of caution — and of imagination — which can add a whole new layer of possibility to your choices.

Most of all, it adds mindfulness to your approach. You’re not making decisions on a whim or on incomplete information. Instead, you’re being intentional with the vision you have for your work and life and how you want to spend your time.

To see some of the simple yet significant factors you should consider regarding your ideal workday, check out this video. To learn more about mindfulness and how it can help your switch careers, take a look at this video.


Trie Angeleva, Career Coach

Mindful Reimagineur

As a Mindful Dream-Job Career Coach, Owner of Planet Reimagine and with Manhattan as her backdrop, Trie thrives when collaborating with others to reimagine their life, work, leadership or organization. She developed and taught Career Success Preparation for The Media School at Indiana University, where she taught 21 classes. A 30-year vegetarian, adopted-dog mom and travel-happy meditator and yogi, Trie is a former CIO and COO and founder of Embark and The Love Monday Method. She has two Master's degrees, six coaching certifications and a certificate in Executive Leadership from Cornell University. Connect with Trie at



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