Chan with a Plan

How to overcome the dreaded resume gap and get back into the workforce with confidence

October 5, 2021


In this episode of Chan With A Plan, host Max Chan speaks with Mimi Moss, Director of Strategic Partnerships at reacHIRE, an organization that works with professionals to return to corporate America after being out of the workforce for an extended period of time. The discussion focuses on various resume gaps, how to address them and strategies you can utilize so you can stay positive, keep your eye on the prize and get back into the workforce as soon as possible. 


  • ”Talking to people and talking to people who know you, who are friends of friends, the more people who know you’re looking the better, don’t be ashamed of [the work gap], just go right out there and talk to as many people as you can and any personal connection, can make a difference [in your job search].” - Mimi Moss [13:01]
  • “I think [recruiters] will continue to be less stringent [on work gaps], I think that they’re seeing that people can come back from a gap, be really productive and that is already happening, and now they’re realizing that this is ok, this can work.”  - Mimi Moss [18:21]
  • “Keep surrounding yourself with people that know you, that support you, that believe in you, so you don’t lose that confidence [when you are struggling to stay positive in your job search].”  - Mimi Moss [41:06]


  • [1:08] Meet Mimi Moss
  • [3:44] Explaining a resume gap properly if you got fired or laid off 
  • [4:59] Quitting a job before you have another one in hand 
  • [6:36] When should you put a work gap on your resume and when not to include it
  • [8:01] Chronological resumes vs functional resumes when you have a long career gap
  • [9:02] What recruiters really think of work gaps
  • [10:36] Addressing your work gap in your cover letter and LinkedIn profile
  • [12:28] Overcoming a work gap through networking
  • [14:14] Types of work gaps reacHIRE has dealt with when working with professionals
  • [15:30] Recruiter’s perception of entrepreneurs wanting to get back into a corporate role after they finished their venture
  • [16:40] Recruiter’s perception of professionals taking a sabbatical and wanting to get back into a corporate role once they are done their break
  • [18:08] Recruiters being less stringent on resume gaps as we move to a new normal of work
  • [20:45] The proper way to address your resume gap or what happened at your last job
  • [23:06] Overview of what a returnship is and how to get one
  • [29:29] If professionals get paid lower than market rate if they have a long work gap and should they negotiate for more money 
  • [30:09] Advice on how to make a good first impression in your first role back from a long work gap
  • [31:17] Discussing whether upskilling is necessary if you have a long work gap
  • [33:42] Thoughts on putting the work experience lower on your resume if you’ve been out of work for awhile
  • [34:40] Obstacles people have about their work gaps and how to own it and move their career forward
  • [36:05] Starting in a new field after a work gap or stick with what you know
  • [38:07] A major career roadblock that Mimi had faced and what she did to overcome it to move her career forward
  • [41:16] Contacting Mimi
  • [42:15] Outro


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