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3 Insightful Questions to Ask Yourself Before You Leave Your Job


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Written by: Grace Bluerock | Seeking Increase

Making the decision to start doing work you love is one of the most important decisions you will ever make in your life.

It can also be one of the most difficult decisions too, but it doesn’t have to be.

It is important to know the right questions to ask yourself in determining if now is the time to start doing work you love.

​I have recently gone through the process of transitioning from my job to doing my life’s work.

During that time, I could see many pros and cons of both, and I spent many sleepless nights going over the pros and cons, hoping that the answer to my question would become crystal clear.

That question, of course, was, “Should I stay where I am or finally start doing the work I love?”

Over time, that answer became more and more clear, and finding that answer within me actually came down to asking the right questions.

I want you to avoid the sleepless nights that can go hand in hand with making a major life decision. As you are contemplating continuing with your current job or making the transition to doing work you love, ask yourself these three questions.

What do I value more, security or passion?

There is no right or wrong answer to this question. Most people value both of these, but usually one of these will be more predominant, depending upon when in your life you ask yourself this question.

So, give some thought to this.

For me, this question caused me to inquire more deeply into myself, invoking the following self-inquiries:

How much longer do I continue to avoid a risk by staying comfortable? Do I stay in a situation that is not in complete alignment with my dreams, or do I step out to express my full potential by following my dreams and helping others to do the same? Do I continue to limit myself to company rules and to state and federal guidelines, or do become my own boss and live and work by my own rules on my own schedule?

Am I living my dream in my current work?

Is your current work in alignment with your mission for your life?

Sometimes, you can bring aspects of doing what you love into your current work. You may have enough of what you love in your current work that you can be satisfied and fulfilled, or what you are currently doing may be the complete opposite of what you love to do.

This is personal for everyone, and only you can answer this question.

Doing the work I love resonates loudly with my mission in a way that no job I have ever had has been able to. What motivates and inspires me in doing the work I love is helping others identify and start living their dream, not someone else’s dream for them, but their dream. I am able to do this through the internet and thus can serve many, creating an unlimited potential to positively affect many lives.

On the other hand, my motivation in my job was about doing what my job description dictated and doing what others (boss, upper management, co-workers, clients) expected of me. By being limited to a particular job and job site, there was limited potential to positively affect many lives.

When I am on my deathbed, will I be happy with the life I chose to live?

I spent six years working in hospice and palliative care and gained so much insight from people who were dying. As they looked back upon and evaluated their lives, there were two main themes I commonly heard:

  • “I wish I had not been so afraid to live a life true to myself, instead of one that others expected me to live.”
  • “I wish I had allowed myself to experience more happiness.”

How would you look back on your life? Did you do all you set out to do? Did you live large? Were you fulfilled in your life’s work? Did you make a positive impact of those around you? Did you leave a legacy behind? Do you have any regrets?

By looking at this question now, you have time to create a life that you can look back on someday and say, “I lived my life to the fullest; I was true to myself; I was happy; I loved deeply; I experienced everything I wanted to experience; and I made a difference.”

Answering the above three questions should give you more clarity and spark new insight into your decision about starting to do the work you love or staying where you are.

By giving deep thought to what you value most, to the extent you are living according to your mission, and what legacy you want to leave behind, you will be much closer to knowing the best and most fulfilling option for you.

Are you ready to start doing work you love? 

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