“Look before you leap” is one of those timeless bits of wisdom that’s stuck around for centuries.
And for good reason.
It reminds us to pause and consider before diving into something new, cautioning us to avoid hasty decisions. But what if we flipped this concept on its head? What if, instead of merely avoiding risks, we used it as a tool to propel ourselves toward success?
This mindset is especially transformative when it comes to our work lives.
As a mindful career and life coach, I’ve found that envisioning your ideal workday is one of the most overlooked yet powerful strategies for creating career happiness. And it’s not just about avoiding pitfalls — it’s about unlocking clarity, focus and purpose. Let’s explore why looking before you leap is so critical.
What Happens When You Leap Before You Look
Leaping in haste limits your success.
Leaping without a plan can lead to missteps — and missed opportunities.
Take Holly, 58, who works at a small government agency. She’d been unhappy for months and wanted a job with more sociability, fewer responsibilities and 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. She realizes serving requires a great deal of energy and menu knowledge, so she thinks becoming a hostess will be the solution. Holly 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 yet familiar that checked several of her boxes, but she failed to consider what her actual day-to-day experience would entail.
Hostess shifts often ran from 2–10 pm, four to five days a week.
The job required her to be on her feet for hours—something her body wasn’t thrilled about.
The pay was about 25% of what servers earned, far less than she had anticipated.
Deflated, Holly managed to hold onto her current role and decided to focus on making it more fulfilling.
What Happens When You Look Before You Leap
Map out your ideal workday before you leap.
Then there’s Calli. Taking time to explore possibilities before making a leap can lead to more fulfilling choices.
Calli’s lived in a college town for decades, but family obligations and health conditions prevented her from completing her college degree. Now 44, she’s determined to graduate. Her enthusiasm is inspiring, but she’s unsure of her career path post-graduation.
She can’t decide what to major in because she has no idea what she wants to do after earning her degree. This uncertainty risks leaving her with a diploma — and a mountain of debt — without a clear path forward.
To avoid this, Calli is now:
Mapping out what her ideal workday looks like — schedule, tasks, interactions, location and the work environment.
Defining her strengths, passions and values.
Identifying roles that align with both her personal goals and professional aspirations.
This process will ensure her investment in education leads her to work that excites and sustains her.
When Looking Leads To A Leap You Love!
Pete had a plan.
Finally, there’s Pete. At 57, 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:
Clarity: He worked with me to define his “why,” pinpoint his strengths, and identify his core values and the impact he wants to make.
Vision: He mapped out his ideal workday, visualizing everything from start to finish.
Research: He explored options that aligned with his vision and goals.
Pete landed a role as a manager at a small winery, blending his love for numbers with his passion for people. Now, every workday feels like a new adventure.
Ready To Leap? Do This.
Know where you're leaping.
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.
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 wise caution — and of imagination — which can add a whole new layer of possibility to your choices.
Most of all, it makes your approach mindful mindfulness. You won’t be making decisions on a whim or with 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. This approach isn’t just practical, it’s empowering. When you approach your career with this level of mindfulness, you’re not just making a choice; you’re designing a future that aligns with your strengths and aspirations.
Want More Guidance On Claiming Your Ideal Workday?
Looking before you leap doesn’t have to be a solo journey.
For more on how to clarify your career goals and create your ideal workday, see if Precision Coaching is a good fit for you. With the right tools and guidance, you can leap into work that lights you up every day.
Why It Matters Now
According to the Bureau of Labor Statistics, the average person changes jobs 12 times over their lifetime. Each transition is an opportunity to get closer to the work that truly fulfills you — but only if you approach it intentionally.
Take the time to look before you leap, and you’ll not only avoid unnecessary detours — you’ll land in a role that feels like home.
>> What strategies ensure a successful leap?
>> Do you have any tips to share for crafting ideal workdays?
Maria Katrien 'Trie' Angeleva Heslin, MA, MA
Certified Coach, Author & Trainer
Dubbed “Professor Dream Job,” by her students, Trie is a former COO and founder of Reimagine Monday. She specializes in helping individuals transform their careers and lives through mindful, strategic approaches. Trie developed and taught career success courses at Indiana University, building on her proven methodology, The Love Monday Method. Her latest release, Launch, designed to help new college grads get unstuck in their search and empower their new career, is now available for Pre-Order.
With two Master's degrees, a Certificate in Executive Leadership from Cornell University, six coaching certifications and a deep passion for guiding new graduates and professionals in their prime, Trie supports individuals in navigating their career paths with clarity and confidence, and is dedicated to helping YOU turn your dream job into a reality.
Connect with Trie at trie@reimaginemonday.com.
