Five Questions to Ask Yourself When Contemplating Quitting Your Job

I still remember it like yesterday: I was offered an ad sales position for a TV company a couple months after graduating college. After thinking, “I don’t know what the hell this really entails,” I accepted the job offer anyway. Like most students fresh out of school, I figured I’d try something new to get me through the door into the advertising world. Maybe after a year or so I’d be onto my next adventure.

Almost two years later, I moved up and past another sales position, until I made my way into the marketing department — the light at the end of the tunnel I was searching for, at the time. Finally, I felt like there was some creative liberty, and some opportunity to leverage what I learned during my sales experience. However, that idea quickly faded as the department underwent four management changes in the span of a year and a half.

During my entire time at this one organization, I was constantly searching for my next opportunity. I was stressed out because of the workload, yet the projects and tasks didn’t require any critical thinking skills. I felt desperate, burnt out and more importantly — unhappy. But I wasn’t ready to quit my job without having another one lined up.

While there were many times I dreamed of drafting a resignation letter, I tried to find new ways to get me what I wanted: a new role that I can thrive in, for a team, brand or organization that I connect with and know my financial worth.

Two weeks ago, I finally wrote and sent that letter of resignation, and this week I start a new position. Though I don’t know exactly what’s in store, over the past four years I’ve asked myself these questions to help me progress in my career.

1. Why am I dissatisfied?

This isn’t always so easy to answer. Sometimes you may find yourself frustrated with the actual work, versus your boss or team, the organization, or yourself and your own lack of expertise. Once you recognize at least part of what’s causing any unhappiness, you can take the appropriate measures to better the situation — and maybe that means removing yourself from it.

I’m a big believer in focusing on what you can control, not what you can’t. If you don’t get along with your manager, then there’s probably room for growth in communication. If you’re not thriving in your role, there’s likely things you and your manager can do to improve that. Those are things you can work on.

Either way, getting to the root cause of your dissatisfaction with your job is key. In NPR’s article, “Want to Quit Your Job? Here’s How to Do it Well,” J.T. O’Donnell, founder of the career coaching site Work It Daily, explains the first step in preparing to leave is to define what you’re looking for:

Run toward a goal, not away from a bad job situation.

2. I’ve submitted countless applications. Why am I not getting any interviews?

Anyone who actively applies to jobs online, knows the feeling of the “application abyss.” When you submit countless resumés, cover letters, LinkedIn messages, to feel like your written experience is entering a black hole.

Aside from the work that goes into curating a resumé, you need to stand out to employers before they even open your resume, and after they have reviewed it. Here are some things to consider:

Copyediting — is your cover letter and online application message free of grammatical errors? Does your experience stand out?

SEO — similar to SEO, your application and resumé should contain key words that align with the job description you’re applying for. Many recruitment systems vet candidates based off matches on key words.

Portfolio — I’m not talking about walking from interview to interview with a big old art portfolio. We’re talking about online content that showcases the best of your work: digital websites, a personal (and relevant) blog, a collection of business partners and clients, etc.

Connections — in a world that is increasingly digital, it’s important to stay connected with your community. That means inviting your prospective hiring manager or HR recruiter into the mix. By introducing yourself via a simple LinkedIn message, you’ll stay top of mind and develop a connection for any future opportunities should the current one not work out.

Enthusiasm — do you really want this job? Or are you just busting through application after application in hope something pans out? Submitting applications only for roles you’re truly passionate about or have a genuine interest in will prove helpful: 1) you’ll spend less time applying for things you don’t care about, and 2) should you land one of these roles, you have a better chance of actually being content with the work/organization. Your eagerness and enthusiasm will also come through in your cover letter and application message (or it should.)

Skills — highlight, underline and bold them! Your skills are your professional appearance, on paper. Bring them to the top of your resume and let them see the light of day. For more on developing and sharpening skills, see question 4.

3. What else can I learn from my role? What about from my employer?

Depending on your tenure and your interest in the position and organization, there may be more for you to learn about in each of these areas than you expected. First off, it’s important to recognize that direct managers are a great resource to start with, but you shouldn’t limit yourself to them. If your boss is equipped to show you the ropes and provide guidance and an educational POV, then great. If not, that’s okay and there are other ways you can take advantage of the wealth of knowledge out there.

Establish a mentorship. As a mentor, you not only distribute your plethora of information onto someone more junior, but you’re given the opportunity to develop an organic relationship with someone on the foundation of mutual interests. With this comes the insight to understanding whether or not you enjoy teaching, and opens the floodgates to more opportunity.

Join in on company culture, if applicable. Some organizations offer extracurriculars like book clubs, sports teams (post pandemic) and other ways to stay connected. No one wants to feel like they’re in high school all over again, but if there’s room to connect with people across teams, gain exposure to new areas, and tap into a hidden interest, then why not? It may introduce you to a new field that could evolve at a later stage in your career.

4. How can I enhance my qualifications and develop my personal portfolio without the financial burden?

Make them pay!

I’m a Capricorn, so I attribute my sun sign to being part of why I’m such a hard worker. My management (in sales and marketing) saw this. Once I was in marketing, a field I more closely aspired to developing my career in, I sought out new ways to expand my education. Last year I started out small and asked the head of our department if she’d be willing to expense a few hundred dollars for me to enroll in day-long content marketing class with General Assembly.

So it wasn’t a surprise when my boss approved this day-long training. Over the next year or so, I continued to succeed in my role, and presented new opportunities to my management for my career growth: a social media and content development conference in sunny Scottsdale, AZ; and a brand marketing course and certificate from Cornell University.

Tip: Understand your employer’s potential budget and do some self-reflection on whether your work ethic and output is deserving of an investment outside of your entitled paycheck. If you decide to ask for additional support or resources, ensure it’s relevant to your current role and is mutually beneficial to you and your employer.

Whether your employer offers to pay or reimburse you for educational purposes, there are dozens of sites like Skillshare, Udemy, and lynda.com that offer online learning tools and resources across industries and price points.

5. I’m not sure what I want to do next, but I’m ready for my next adventure.

If you don’t enjoy your work, then it might be time for you to do more self-exploring and trying a career in something you love. If you don’t know what that is, picking up a new activity on the side and starting a 5–9 while you get through your 9–5 is always an option. I suggest looking at the possibilities of integrating your longtime, or new-found hobby into a career.

Good news is: things have changed! People don’t usually stick to a 30+ year tenure as they once might have. If you want to do something for a few years, and then decide it’s not for you, that’s okay. Experience is the art of opportunity.

Your mountain is waiting

If these five questions weren’t helpful, Norman Ellis, a longtime marketer on the search for his own next adventure, shares seven questions to ask yourself when pivoting careers entirely during the pandemic. One thing is certain — you should identify your strengths and challenges before taking on new opportunities.

If your current employer’s HR department offers career coaching, utilize it! They may be able to suggest open roles you’d be a great candidate for or keep you in mind for future positions. No career coaching? No problem. The Clifton Strengths Finder Assessment is a great resource for career development. It collects your responses to a series of questions, identifies your strengths and how your strengths influence one another.

NPR’s podcast, Life Kit, shares tools to help you “get it together” and preserve your mental health when your emotions are taking control at work, but also how to leave a job graciously once the time comes.

Maybe you’re a writer who loves landscape photography — how about pursuing a career as a travel journalist at National Geographic? Or maybe you’re an animal lover volunteering with the ASPCA while you plan your own business strategy. Wherever your career takes you, here’s a reminder to take with you.

You’re off to great places!

Today is your day!

Your mountain is waiting, so …

Get on your way!

— Dr. Seuss