Even the most confident women I know struggle with the decision to resign from their job and move on to something else. Lately, I’ve seen many women in my life jumping ship: they have looked deeply into what makes them happy and came face-to-face with the future staring back. The road they take isn’t without some nerve-racking potholes: resigning from secure jobs, ditching stable clients, taking (gasp) less money, and quitting without having a new gig lined up. They attend workshops on how to freeze eggs, revisit family planning and blaze a new path against the advice of significant others.

But is there some secret guiding them? Not at all. Like many women making a drastic change in their lives, they struggled with the unknown.

Few of us make these decisions lightly. Some of the things you may weigh before making the change could include factoring in what you will lose –– or at least, what you think you may lose. Here are five questions you should ask yourself before pulling the trigger on such a life-altering decision.

Why Change Your Life and Start a New Career?

Why not be happy? You’ve been in the same position long enough to see the company change, and you are no longer satisfied with your job. This is what tipped the scale for my friends:

• Your role changed. A friend of mine was bumped to another section; one minute she’s leading a multimillion-dollar growth initiative at a company worth $40 billion, the next she’s assigned to the tedium of the corporate strategy unit because her company lacked a culture of experimentation. She knew her value and quickly started the job search, receiving offers from both Twitter and Facebook. She is now enjoying her new role as a product manager at the latter.
• You deserve career advancement. Another felt that the small team did not allow for growth. She wrestled with moving out of EdTech, and only after months of soul-searching and career coaching found a perfect fit as an interactive producer for an advertising agency.
• You’re seeking a challenge. One reached the top of the ranks and was running the place like a champ, but became bored with the minutia. She craved something more creative, and rather than taking a similar type of job with Pandora, opted for a pay cut and now serves as a project manager for a highly-regarded agency with clients like Netflix, Amazon and Google.
• You’re in the wrong industry. Two friends, after years of law school and big firm work, found themselves in what was (for them) the wrong career. One went directly into nursing school, while the other lived off savings, taking time off to find the “right” job — and is now director of development for a solar energy company.
• You need a better environmental fit. A different friend’s favorite boss left, leaving a management void in an already negative company culture. She left to spend a year at home with her two young kids before landing a program management position at an innovative technology company.

The result?  I can assure you that none of them have ever looked back.

What Matters Most in Your Career?

Here are some common answers I’ve seen:

• Flexibility. You like the prospect of having more time to travel or work on personal projects.
• Learning. You’re looking for new challenges.
• Ownership. You want work that matches your need for a sense of fulfillment.

We want money, yes, but we also want a job that suits our lifestyle — which could mean fewer hours, nicer people, more freedom of choice, childcare on site, bringing our dog to work — and anything else that will make us happy.

Other things to considering include: Do you have the support of your significant other? Are you planning on conceiving soon? Adopting? Freezing eggs? Remaining childless? Considering what that means to you and your career, taking stock of all of these things can contribute to your decision. We tend to feel more at ease when our personal and professional lives co-exist in harmony.

What Am I Afraid Of?

Many are afraid of leaving a career they’re good at, the potential for short-term financial insecurity, needing to dip into savings, the lost camaraderie of current workplace friends, or fear having to start over at the bottom. Rest assured, however that virtually all of these fears are experienced by confident women who make successful career transitions.

One such woman, Gazelle Javantash says, “Considering how much I spent on my education and a Master’s degrees, I told myself I couldn’t start at entry level with this much debt. So I hired a career coach.” Through this process, Gazelle moved from education into the private tech sector. Her coach helped her to weigh all of these questions and identify what role she wanted her career to play in her life.

What Do I Have to Gain?

This is different for everyone. Maybe your desire comes from career and personal satisfaction, you anticipate this new role giving you more free time, or this new direction provides the financial boost to start saving for retirement or a home. In any case, confident women who make career transitions know that they all require a leap of faith.

How Do I Ultimately Decide?

So how did all of these powerful women in my life come to the decision to pick up their padfolios and hit the road? We talked to our partners, and we talked to each other: most of us, in fact, had been thinking about jumping ship for months. We would casually mention the idea in passing — over a glass of wine, in the pool, on an airplane, or while hiking up a mountain. We listened to one another, helped each other weigh all of the pros and cons, asked ourselves what we had “to lose”, and then finally delivered our recommendation to the others.

Ultimately, no one else can make that decision for you. Everyone will give you advice and try to help, but in the end you are the only one who truly knows what’s right for you. In your heart, you will know when it’s time for a change when it’s time to move beyond your comfort zone and into the unknown. The final decision will not be easy; it’s never easy to take a left onto the road less traveled and dive into something new. While change is inherently scary,  you know in your gut when it’s required to fulfill you. And once you do decide to take that first step, don’t look back. We did it, and you can too.