But What If: 4 Questions People Asked When I Took a Leap of Faith

I didn’t come into 2023 guns blazing, ready to quit my career and start a new chapter book. 

There may have been some internal whispers of “but what if I just don’t show up?” when people put last-minute meetings on my calendars, but I wasn’t planning what’d I’d say in an exit survey or anything like that. (Ok, maybe a little…)

So when I quit my job, it didn’t just catch me off, guard. My friends and family were taken by surprise as well. 

And because they love me, they started asking questions. All with good intentions, but after the third or fourth time, I began questioning myself. 

Even though I was concretely aware of all the possibilities that could arise, good and bad, and had plans for them all, tumbleweeds of doubt started appearing, spreading little seeds of worry. Super unhelpful.  

But what if pin cover

So I wanted to share the four, “but what ifs” I was asked the most through this process, so you can prepare for similar questions when it’s your turn to step into uncharted waters. 

Buckle up. 

4 questions people asked when I took a leap of faith

​​Leaving a job can be a difficult decision, often accompanied by a range of emotions and fears. When I quit my career, I found that there were four common questions that people asked me.

But what if they let you go on the spot?

Although it’s common in the United States for there to be two weeks between when an employee submits their resignation and their last day of work, sometimes that’s not the case.

Sometimes it’s longer. And sometimes it’s shorter. Sometimes they fire you on the spot, “effectively immediately,” and all that jazz.

So it was only natural that I was asked a common question: “what if they ask you to leave immediately?”

Well…I have enough of a cash cushion that a few extra weeks or months really wouldn’t make or break me. So if they slam the door in my face immediately upon my notice, it’d be jarring but not disastrous.

But also…and I may be playing devil’s advocate here, this scenario will not be possible. Hell, in today’s economic environment, I could have been laid off or fired, where I may have had more financial support (in the form of unemployment and severance) but would likely have been less mentally prepared.

Or. I could have stayed and been a crab apple. 

No easy answers here. But wildly different implications. 

Tip: If your answer wouldn’t be similar to mine (i.e., you have enough cash to tide you over), wait to give your notice until you do, in case this exact scenario comes to fruition. 


    We respect your privacy. Unsubscribe at anytime.

    *Free On-Demand Masterclass*


    Less stress & more confidence…in just 25 minutes.

    But what about health insurance?

    Benefits such as health insurance and retirement plans are important considerations when leaving a job. 

    But here’s the thing. According to the US Bureau of Labor Statistics, 9.6 million people are self-employed in the US. And while that’s only about 3% of the population – it’s still almost 10 million other people with the same conundrum.

    So there are clearly solutions—another way of doing things. 

    Did I have some learning to do? For sure. Does the cost of insurance jump a pretty penny when an employer does not sponsor it? Yup.

    But financial literacy never really ends, so if I wasn’t learning about self-employment retirement plans or health insurance, it would have been something else. And the extra cost was not worth more than a level of freedom I haven’t had since my playground days.

    Time (and money) well spent, in my opinion. 

    Tip: Check out healthcare.gov for information on self-employed health insurance & fool.com for insights on saving for retirement

    But what if your business fails?

    This is the most common question people ask when someone quits their job. And it’s a valid one – we all need money to survive. 

    but what if your business fails?

    But I had a clear idea of what I wanted to do next and was confident I would find a way to make it work. And if it didn’t work? Well, I had a plan for that.

    Here’s what that plan looked like (at a very high level):

    • Worst-case scenario: I run out of savings and have already sold my car, exercise equipment, and furniture. I’m out of time.
    • Plan: I move home and use the energy I’m no longer using for pure survival to find other means of earning cash and get back on my feet.
    • Likelihood of this happening: 2/10. 

    A 20% likelihood that my world would implode was not worth staying in a corporate gig. The possibility of autonomy was far more attractive. 

    Tip: Read The 4-Hour Workweek by Tim Ferris for the journaling prompts I used to make a plan for my worst-case scenario. 

    Are you sure?

    Regret is a common fear when quitting a job. 

    But again, I found that the possibility of regretting not leaping was more significant than the possibility of regretting taking it. In the end, I knew that I wouldn’t be happy staying in a job that didn’t fulfill me and that regretting not pursuing my dreams would be worse than regretting taking a chance.

    So when someone asked me if I was sure about my decision?

    The answer was “hell yes,” no eyelashes batted. 

    Don’t let “but what if” stop you from choosing joy

    Taking a leap of faith can be scary for you and the people who love you.

    But it can also be incredibly rewarding. 

    It’s important to acknowledge the fears and concerns that come with it, but don’t let them hold you back from pursuing your dreams. Plan for them. Be ready. Do your research

    And then go for it.

    Join the Newsletter

    Subscribe to get my latest content by email.

      We won’t send you spam. Unsubscribe at any time.

      Share your thoughts!

      %d bloggers like this: