Questions to Ask Yourself When You’re on the Verge of a Career Change

The right questions can help clarify your biggest challenges and hidden opportunities says executive coach Karen Elizaga.


Leap and the net will appear. Follow your passion and the money will follow. The current narrative in career growth can make it seem as if embarking on a dream career is as simple as tying our shoes. The reality is, giving up a cushy yet unfulfilling job for the entrepreneurial path often involves taking on substantial risk, navigating financial insecurity, and overcoming strong social conditioning. It’s not just about next steps—it’s embracing a whole new identity.

Yet, there’s a pretty major upside in what executive coach Karen Elizaga calls finding your own personal “sweet spot,” or the point where your passion meets your purpose. “Living this way makes you feel like you on your best day,” she explains. “You realize you never have to dread another day of work in your life.”

She understands the fear before the fire all too well. Karen rose up the ranks as a corporate lawyer and business exec in New York and the UK for years, battling her own personal fears and parents’ expectations that she stay the course in corporate, before deciding to go after the more uncertain entrepreneurial path of coaching.

Yet, after coaching everyone from C-suite execs to organizations for more than 15 years, she’s learned that personal transformation is possible and it’s not about undue effort or force. “Simple shifts in mindset lay the foundation for change,” explains Karen. “It’s really about cultivating confidence and taking forward action.”

And to do that, it’s about asking yourself the right questions—they can set a whole new tone and make the impossible possible. Here, she shares the key questions she asks her clients to get them to burst through the mental blocks that prevent them from uncovering and doing what they love.

What do I want to do?

It seems pretty simple, says Karen, yet it’s a question that doesn’t often get asked in the work realm, because we’re so focused on what’s currently available. “It doesn’t have to be limited to just what you do at work,” explains Karen. “For example, as a lawyer, my analysis doesn’t have to be, well, do I like being a lawyer? It could be something broader. Like, do I like mediating conflict?” Asking the flip side—what am I not good at and what don’t I like to do?—can also work,” says Karen.

What’s worth my time?

“What I’ve always said to people who have families or are imminently thinking about having a family, is that you’ve got to find what drives you from a heart standpoint. Maybe it’s financial, or educational or something that deeply fulfills you on a spiritual level, but it’s got to be able to counterbalance the tremendous love you have for your child. Otherwise, it’s going to create resentment and unhappiness.”

What am I afraid of?

The top thing Karen sees in people on the verge of change: Fear. People are afraid to put themselves out there. They’re afraid that they’re not good enough. It’s comfortable where they are and they’re afraid if they make the change, they’re not going to cut it.” Body language also play a role. “Often they’re not holding themselves with confidence and comfort. Their body language betrays them.” To get over these hurdles, Karen says it’s important to strive for excellence versus perfection. “With excellence, there’s room to try and fail and have fulfillment and enjoyment in the process of getting there, as opposed to just looking for one outcome.”

What value do I bring?

“I see it in both men and women but I see it more in women. Women don’t hold themselves out as experts as readily as men do,” says Karen. “One of the things I like to get women to focus on is the value they bring. If you ask yourself what value you bring, you’ll come up with a really good answer. If you ask yourself a different question like, when are they going to figure me out? Then you’ll also come up with a good answer—to make yourself feel less than.”

What am I grateful for?

“Another really simple thing is gratitude practice. If you can open your eyes every morning and count five things you’re grateful for, you start your brain off in a really positive and productive way of thinking as opposed to opening your eyes, and then immediately asking yourself: how am I going to screw something up today? and working yourself into a tizzy.”

Am I overthinking it?

At some point, you just have to jump, says Karen. “When you’re overthinking it, chances are you’re not moving. If you write down your goals every month, and you look at last month and see you’ve achieved them, you’re likely on course. If you’re rewriting the same goal from last month and next month is the same thing, chances are you are overthinking it.”

What would happen if I didn’t do it?

“Ask yourself: what’s the compelling reason that you need to do this? Is it going to change your life in a positive way? And on the flip side, if you don’t make this change, how bad is your life going to be? Imagine the best and worst-case scenarios. Either of those things is going to be pretty compelling and move you to take action. You’ve got to have your motivating reason otherwise, it’s just a thing on a piece of paper.”

What’s the real reason?

Discovering the humungous, hugely motivating reason that you must do X, is key, says Karen. “If you ask yourself ‘why,’ like, as in, why are you doing that? Generally people respond with, why are you asking me like that? ‘Why’ is a terrible word because it kind of makes you put your guard up. Remember the last time you came down the stairs and your mom said to you, ‘why are you wearing that?’ She could’ve meant where are you going and what’s the occasion? but wouldn’t what’s the occasion?’ been a much better question? It evokes a different thing. In asking yourself what’s your humungous, gigantic reason you need to do this now? By asking yourself this one question, you’ll get the answer that unlocks everything for you.”



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