3 essential questions
Whether you’re pursuing a passion, exploring a side hustle, or simply seeking a new challenge, deciding to quit your job for something new isn’t as simple as it sounds. It requires careful thought and planning. I can speak from experience—when I founded Jobprofile, I had to make that difficult decision myself. And over my 25 years in this field of coaching and recruitment, I’ve heard countless stories from candidates who left stable jobs at prestigious companies like Microsoft, PMI, Nestlé, UBS, JTI, and Pictet to follow their passion full-time.
They loved their jobs, but the more they reflected on their core values, life goals, and how they wanted to use their skills, the more they realized that entrepreneurship or a major career change was the path forward. Many had nurtured their passion projects as side hustles for years but still faced nagging questions:
– Why should I quit to make this my full-time job?
– Is this really what I want?
– When is the right time to quit?
The most common question I heard, though, was: “Will I regret not giving this a shot?” The truth is, deciding to leave your job is more complex than it appears. Let’s break it down by focusing on three essential questions: Why, What, and When.
WHY (Do You Want to Change?)
Start by asking yourself “why” you want to leave your current job. Consider the old adages: “The grass isn’t always greener,” and “Know what you’re running from and what you’re running toward.” Is it the company culture that’s draining you? Are the people or projects unfulfilling? Or is it something deeper, like a desire to build something new or work in a different industry?
Be brutally honest with yourself. It’s critical to get clarity on what’s driving your need for change. Before you quit, try to get a taste of what the new role or industry might be like. Does it feel better than what you’re doing now? Is the potential change worth the commitment?
If possible, take some time off to focus solely on your passion project, or spend your free time experimenting with new industries or roles that interest you. Volunteer, shadow professionals, or conduct informational interviews. Keep the end goal in mind. Visualize the kind of life you want to build and ask yourself if this new direction aligns with it.
When coaching clients, I often recommend they sit down and write a “future autobiography”—a detailed account of what they want their lives to look like in the years ahead. It doesn’t have to be long, but it should include what matters most to you, how you want to spend your time, and what you want to be remembered for. This exercise can provide a lot of clarity.
WHAT (Do You Want to Do?)
The next step is to assess yourself. While some people know exactly what they want next, many don’t. And it’s impossible to figure out your path forward without first understanding where you are now. Ask yourself:
- What’s my end goal?
- Will continuing what I’m doing today bring me closer to that goal?
- Will my 80-year-old self have more or fewer regrets because of my current choices?
Once you’ve answered these questions, write down the steps you’ll need to take to make your future self proud. Also, outline potential obstacles. This self-awareness is key because it helps you identify the challenges that could prevent you from moving forward.
One common challenge I’ve seen with clients is the unpredictability of income, especially when leaving a stable corporate job for an entrepreneurial or freelance venture. Instead of obsessing over the financial risks, think practically: If quitting gets you closer to your goal, how will you manage any financial shortfalls in the short term?
Experimenting is part of the process. Career transitions aren’t formulaic, so approach them with curiosity, a willingness to learn, and the patience to experiment.
WHEN (Will the Change Happen?)
Expect setbacks. Unfortunately, career transitions are often harder than they look. Hiring processes tend to favor past experience, and recruiters may nudge you towards roles similar to your current one, even if you have the skills to make a leap into a different field. However, you don’t need everyone to take a chance on you—just one person who believes in your potential.
Be realistic with your timeline. Major changes, such as transitioning industries, roles, or even geographical locations, often take longer than expected. Remember, we tend to overestimate what we can achieve in one year but underestimate what we can achieve in ten. Gradual changes are often more sustainable, and small, consistent actions can lead to exponential results over time.
Setting a realistic timeframe is essential. For example, if you’re trying to transition from a legal role in data protection to a data governance specialist, give yourself a year to acquire the necessary skills and build relationships with industry professionals. If it doesn’t work out in that timeframe, reassess your goals and decide whether to extend your timeline or explore other options.
Also, always have a backup plan. This doesn’t mean settling for less, but creating an alternative that bridges the gap between where you are and where you want to be. This will help you stay resilient when things don’t go exactly as planned.
Conclusion
Quitting your job for something new is a complex, deeply personal decision. It’s not just about switching careers—it’s about redesigning your life. By focusing on why you want to change, understanding what you want to do, and being strategic about when to make the move, you can make this transition with more clarity and confidence.
Take your time, experiment, and most importantly, be patient with yourself.
