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Should I Stay or Should I Go?

Updated: Mar 28, 2019

Four years ago I had to have a really difficult conversation with my boss at the time.  I had just been head-hunted to join a fast-growing, well-funded start-up* and the opportunity seemed too good to pass up, despite the fact I wasn’t looking to leave my current role.  

My boss, a seasoned CEO, took the information in stride, despite the fact that if I did leave it would create a huge headache for her.  Upon hearing my choice to stay or go, she provided incredible advice:

She said,

“The beauty of getting an unsolicited job offer is that it forces you to step back and think through three different outcomes.

It causes you to think:

  1. ‘Actually, I really like my current role, but there are things in this role that I want to fix or change moving forward to make this work.’

  2. ‘Wow, this new offer is exactly what I want to do and I’m going to go forward with it.’

  3. Or, it can cause you to think: ‘This job offer isn’t what I want, but it makes me realize that I do want to look for other roles outside of my current role.’"

Beyond just a lesson in how to respond with grace and generosity when one of your employees comes to you with similar information, I love this advice because of what it highlights about how we think about and make pretty significant decisions.  

I’m a person that is highly susceptible to flattery.  So, receiving an unsolicited job offer played right into that weakness.  Despite my boss’ fantastic advice, I didn’t fully consider Option 3. I knew that my current role wasn’t going to be for me for the long-term, and it was too hard to pass up an opportunity that had found me...and one that kept telling me how wonderful I was.  The offer-in-hand had certainty and a clear timeline. I was going from one certain outcome (my current role) to a new certain outcome (a new role). Option 3 was off the table.

Why is it hard to go with Option 3? One reason it’s hard is because of the Streetlight Effect (also known colloquially as the Drunkard’s Search Principle). It’s a cognitive bias we experience when we search for things where it is easiest to look (for example, right under a streetlight as opposed to other parts of a dark street).

Options 1 and 2 are right under the streetlight. The Option 3 jobs - though they may be filled with rainbows and butterflies and unicorns - are in the dark, so we don’t evaluate them.

We know the why, so now the question is how: how can you think through Option 3? And, how can you evaluate Option 3 when you are swamped with your day-to-day job and just don’t have the mental space to be proactive?

Like slowly building a farm team, a concept we talked about a few months ago, Option 3 can be broken down into micro-steps:  a set of small, snackable tasks that you can undertake to make the whole ‘job-search-when-you-really-don’t-want-to-be-job-searching’ process a bit more palatable.  

The Clash ask: "Should I stay or should I go?" But, all good Karaokers know that the second verse of this iconic song asks, "Should I stay or should I go now?" Here is a list of tasks that help you to evaluate what you need in your next role and determine if the answer to the second verse is: "I should go later".

The Lunchables™ Approach to Figuring Out Your Next Role

1. The Intention Statement

  • At the beginning of every yoga class, there’s a few seconds of intention-setting - why you’re in the class that day and what you’re hoping to accomplish. It’s a lovely exercise in pausing to be thoughtful instead of just barreling forward with the next activity.  

  • To start out this quasi job search, set an intention for the search.  In a few sentences, write out why you’re embarking on this process (e.g., could be what you’re missing in your current role), what you’re hoping to achieve and what you’re looking for in your next role or next step.  

2. MadLib Job Dimensions

  • Like a life partner, every job is filled with a set of compromises and deal-breakers.  Yet, we often don’t explicitly think through all of the dimensions of a job and what is most important to us at each step in our careers.  

  • Step through each dimension of a job:  Role, Organization, Life Needs (template here) and write down what you want in each.  For some the dimension won’t matter, but in others it will - e.g., you don’t care if you work in the healthcare industry or the education sector, but it’s really  important that you work for a small company. Once you’ve gone through each dimension, choose your deal-breakers - those dimensions you must have in your next role.

3. The Envy List:

  • Don’t get me wrong, I’m quite happy with my role as an amateur blogger.  Yet, I have one friend whose job I am insanely jealous of - she works for a cool company, has a small awesome team, gets ridiculous travel perks, and has a sweet comp package. I find it helpful to think through why I am jealous of her role and what components of it I could incorporate into my current or future work.  

  • For your Envy List, make a list of five people whose jobs you envy. And,  for those people you know, grab a coffee with them and understand more about what they do, what’s their most favorite part about their job, what’s their least favorite.

4. The Elevator Pitch

  • Start to jot down what your ideal job would look like using what you learned on the Envy List and the Mad Libs exercise.  Distill the description of your ideal job into a single paragraph that you can share with others (you can get into more detail later - keep this one simple!)

  • For example....“I’m looking for an operations role on the leadership team of a small and scaling start-up (Series A or B) in the Austin area in the fintech space.  I’m looking to bring my past experience in finance, operations, legal, and HR to lead these functions in the organization”

5. The Strength of Weak Ties List:

  • There’s some research somewhere that says that you’ll likely get a new job not through your immediate network of close friends, but from the second and third tier connections.  We often ask our immediate network if they know of any roles that would be interesting to us. Instead, ask your immediate network to put you in touch with interesting people.

  • So, your micro-step is to email 15 close friends or colleagues stating that you are exploring other roles (include your Elevator Pitch) and ask them to introduce you to three or four friends of theirs who they think would have an interesting perspective to share. (Being specific is key - "don't say "do you know any interesting people?"; rather ask "could you introduce me to three friends...?")

One suggestion…. give yourself one small task a week to do.  Don’t think about the next task on the list or try to do all at once.  Recent research shows that precrastinators (those of us who - when assigned a task - immediately want to check it off of our list) could benefit from going a bit slower.  

Of course, updating your resume, cleaning up a cover letter, speaking to recruiters, among other things, are also important parts to a job search.  This particular list of micro-steps is meant to get you thinking and expand your awareness of what other roles are out there. It’s meant for you to be thoughtful and holistic about what you want and need in your next role.  When I was faced with my job decision four years ago, I didn’t do any of these micro-steps. In retrospect, I probably would have made the same decision and gone for the new role, but I would have made the decision with a little more data and a little less emotion and ego.


  • A job offer is helpful in pushing you to think about if you want to stay in your current role, if you want to take the new role, or if you want to look for another role outside of your current company.   

  • There are a number of small steps you can take to better inform what you want and need in a new role; and how you can start to build a network of people who could support you in finding a new role.

  • These steps include setting an intention; clearly articulating job dimensions and prioritizing those that are most important to you; honing an elevator pitch; and listing people who can support you in this process.  

  • These are called micro-steps for a reason! The idea is to tackle one at a time and let the learnings from each step inform the next step.  

* Note that all start-ups when they are trying to recruit you are “fast-growing” and “well-funded”.  Whether that is actually the case is an entirely different story.


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