#001: Afraid to quit your sales job without landing another first?

Jul 25, 2023

Why this approach is keeping you stuck in an unfulfilling job loop and what to do instead.  


One of the biggest reasons you might be stuck in an unfulfilling career is that you don’t feel confident quitting your current job unless you have another one to go to.  

If you are a high performing salesperson, you are particularly susceptible to this trap. 

In this post, I will outline why this is a limiting approach and what you can do instead. 


It’s complicated: Your relationship status with work

There are reasons why securing another job first makes sense.

Doing so allows you to guarantee another source of income before forfeiting your current one. It might also raise less questions for potential employers if you are still employed. 

However, I see this approach as flawed.

Waiting to find your next role before giving notice to your current employer is like waiting to find your next romantic relationship before you’ve broken up with your current partner.

You need time to tie up loose ends and emotionally prepare yourself to get back in the career dating pool. 

Salespeople are particularly susceptible to this thinking. To be successful in sales you must always be chasing something. There is no chance for stillness.

Chasing your next role before quitting is simply an extension of your current work habits.


Finding a marginally better position 

The job search process can be exhausting so it makes sense to simplify it in the hopes of finding another job sooner.

Simplifying the process often involves:

  • Looking for the easy job you know you can get but that has some additional perks. E.g. slightly better pay, more promotion opportunities, working B2B instead of B2C. 
  • Basing your job search on finding the opposite of what you don’t enjoy about your current job. E.g. a fully remote role because you dislike commuting to an office.
  • Relying on who you already know in your network. This can be an issue if most of your network is made up of people just like you working for similar companies. 

Basing a job search on these elements often leads to one of two outcomes:

  1. You take a job that lands you in only a marginally better position relative to your current position. 
  2. You can’t find exactly what you’re looking for so you stay in your current job, hoping if you wait long enough that the perfect opportunity will come along soon. 

In both scenarios, your lack of career fulfillment remains.  

Experience your life without a job title

When you become too absorbed in work, you forget what it is all in service of: the life you get to experience.

To find a fulfilling career, I strongly believe that you first have to shift your focus entirely away from your career. 

You can do this by leveraging the power of an intentionally designed, extended period of time away from work. This is not a one week holiday at the beach to clear your head and relax.

This is a focused period of time that you dedicate to a specific activity, hobby or goal that is unrelated to your current career. 

I call this a Gap Month. 

In a Gap Month you might:

  • Start writing that book you’ve always wanted to write. 
  • Take that course and learn how to day trade on the stock market. 
  • Pick up surfing again. 

What you choose to do with this time will be unique to you. Regardless, you will discover what life feels like when the busyness of work is taken away.

It’s a complete perspective shift from which you can make a clear and empowered decision about your career. 

You can take a Gap Month while still employed or you can quit without another job and take a month off before making any career moves.

Either way, putting the timeframe of one month on it, allows you to enjoy the time without placing unnecessary pressure on yourself to force a decision.

In summary

If you are feeling unfulfilled in your current role, waiting for the perfect job to come along before you quit is not an effective approach.

Taking an extended break from work to focus on your life is a far more effective place to start. 

What you do in this break may not directly lead you into your next career but it will give you the mental and emotional break to remind yourself of what you want to experience in your life. 

Actionable steps you can take

  1. Set up a new note in your phone and title it “My Gap Month”.

  2. In this note over the coming week, brainstorm ideas: what is something you’ve always wanted to spend more time doing? Who would you love to hang out with? What time would you wake up each day? The more detailed the better. 

  3. Research an epic adventure based on one hobby you are already interested in. E.g. kayaking: is there a remote cabin on a river somewhere that other kayakers have stayed in and raved about?

I’d love to hear what you come up with - send me an email [email protected]


Alana Kilmartin



Taking extended and intentionally designed breaks from work is what I specialize in. If you know this is what you want but don’t know where to start, you can book a free discovery call with me using this link




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