5 Career Change Questions to Ask Before You Make the Leap

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In the midst of 2021’s Great Resignation, people in all different career sectors started to explore the possibility of a career change, leading to huge numbers of workers leaving their jobs for something they hoped would be better. The number one reported motivator? A better work-life balance

While the idea of switching careers might sound enticing to you, it’s important to consider how this large change could potentially impact both your personal and professional life before making the leap. For individuals quickly approaching retirement, it’s even more imperative to explore how a change in plans could affect their financial planning and lifestyle down the road. 

Today, we want to look at eight questions based on a structured decision-making model to guide you in your career change, each designed to help you gain further insight into your motivations.

To give you a little context behind this list of questions, they follow the structured decision-making model, which follows these core principles:

  1. Identify objective
  2. Identify benefits
  3. Calculate costs
  4. Consider alternatives (including risks and benefits)
  5. Decide whether benefits outweigh costs

Applying this model in the context of changing careers can help you decide the best course of action as you move forward. 

1. Why do you want to switch jobs?

Before you make any major changes, you need to ask yourself the big question: why?

A career change isn’t a decision to make on a whim—it can be a lengthy and complicated process. You need to be motivated to follow through with your career change, even when the going gets tough. 

Is it for the sake of finances, or to pursue your passion? Maybe you feel like a change of pace is the only way to preserve your sanity at the moment. 

Keep asking yourself “why?” to get to the heart of what it is that you truly want in the context of your values. For example, if you’re thinking fewer hours, why? Do you want to spend more time with your family? Shorter days or longer vacations? What’s at the core of these desires?

Whatever reason you’re considering a career change, finding a core motivation tied to your values can help you stay on track throughout the entire process. 

2. What will you get out of the new job or career?

This might seem similar to the last question, but it’s a little more nuanced. Whereas the first question is getting at your objective, this next one is evaluating the benefits of a career change with this objective in mind. 

Think about what your ideal position or career would look like. You already know what your current job offers—you’ve lived it day in and out for years, maybe even decades. Now it’s time to let your mind truly explore the possibilities of what a career change could bring into your life. 

Ask yourself, “In what ways will the new career give me more of what I want from life?”

Maybe some of the things you’ve been missing out on—like meaningful work relationships, flexibility, room for advancement or higher pay—could be on the horizon with this new career change. Let yourself dream, while also being realistic: What do you envision for yourself?

3. What are the drawbacks of this new career?

Even if you feel ready to move on from your current career, it’s worth it to consider what you’d potentially be losing out on by switching things up. 

There are pros and cons in every job, and if you’re considering a change, chances are those cons have really been sticking out to you. But take a moment to think back on your time there—what good things could you be losing through this change?

Relationships with coworkers, a great office environment, flexible hours, room for advancement, higher salary, or even just the predictability and stability of having a history there—the possibilities are endless.

How will this impact your other goals and priorities?

Think big picture here. The decision to make a career switch can be life-changing, and you’ll need to look beyond the immediate future to keep the big picture in mind. 

Retirement is always closer than ever. Ask yourself how this career move could impact your retirement plans, assuming everything goes according to plan. Just as importantly, ask yourself what could happen if things don’t go exactly to plan. 

If you’re starting over in a new field, it will take some time to gain the knowledge and experience necessary for success. Are you willing to change your current lifestyle, and even potentially downgrade your lifestyle in order to pursue your passion?

And even if you’re on board for the challenge right now, you’ll need to consider how a decreased salary will impact your lifestyle down the road. Is “future you” going to be okay with a delayed retirement or a lower quality of living?

Let’s take a moment to consult with future you…

What if you don’t?

Imagine your best life in 10 years on the same track that you’re on—are you happy, or do you have regrets?

What if you do?

Now, imagine your best life in 10 years with the change you’re considering. Does it light a fire that makes all of the potential obstacles worth it?

How will this career change affect your mental and emotional well-being? Do you see yourself having more or less time with your loved ones, and will that affect your relationships with them? 

These often-overlooked questions are important to consider. A career change doesn’t just affect who you are in the office, it has the potential to ripple out and touch other areas of your life, too. 

4. What are your other options?

Before you jump in, you’ll want to consider if there are any other alternatives. Do you see any other routes to achieving your goals? If you want to cut back on hours at the office, maybe you could negotiate a day or two week where you work from home. 

You may find it helpful to journal these alternate plans to visualize how they compare to one another. What are the drawbacks and tradeoffs for each of your options?

Of course, depending on your situation, sometimes there are no viable alternatives. But it’s important to consider them before moving forward.

5. Is it worth it?

Only you can decide what the best course of action is, because it’s your life. 

Now that you’ve explored all the possibilities, how do you feel? Do you feel like the benefits outweigh the costs? In the face of all the obstacles ahead, do you still feel excited about making this change?

If your answers are yes, then we wish you the best of luck in your new endeavor! 

Changing careers at any age can be complicated, and the closer you get to retirement, the more moving parts you need to consider when making such a move. 

With extensive first-hand experience and over a decade of helping our clients through major life transitions, we know how important it is to pursue your passions. Here at Clarity Wealth, we take pride in helping you navigate a career change and plan the financial future of your dreams. Schedule a meeting with us to get started.


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