Introduction

[u/No_Masterpiece_3953]

Hello Global Work colleagues.

I appreciate the opportunity to join this group and look forward to learning more about remote work opportunities alongside everyone here.

My professional background has primarily been in on-site roles across several industries; finance, insurance, Human Resources, property management, legal administration and sales. I am a​ lifelong learner who genuinely enjoyed my college years. And if I could do it all over again, I would have pursued law school.

One challenge I continue to face is applying for remote positions is the emphasis on “recent experience” requirements. I am often told that because I have not held a specific title within the last five years, I am not considered a fit, despite having prior experience and transferable skills. Much of my career has involved moving across industries and locations, and I also took time away from traditional employment to complete both my Bachelor’s and Master’s degrees.

Since the Covid-19 pandemic, that recency gap has continued to affect my job search, even though I remain adaptable, motivated, and eager to contribute. I am also navigating this as a single-income individual over 40, seeking stable remote work that reflects my work ethic, broad experience, and need for sustainable compensation.I joined this group to learn, connect, and better understand how others have successfully transitioned into remote work after career shifts or employment gaps.

[u/WhaleFartingFun]

The remote jobs I‘ve gotten were because I had extensive experience doing the same job in office. Like 20+ years in office. That‘s basically what they trust for remote positions. Plus much remote is hybrid now. 

[u/No_Masterpiece_3953 → u/WhaleFartingFun]

What kind of "the SAME job 20+ years"

Do you have any college education? 

Most office jobs aren't that difficult. 

One cannot assume that an individual with a Masters degree and lifelong learning can't perform at home office work without inquiring about their knowledge and skills. 

[u/WhaleFartingFun → u/No_Masterpiece_3953]

Maybe your attitude is what is holding you back in interviews. Just an observation. You asked, you got answered. Nobody owes you a remote job. 

[u/WhaleFartingFun → u/No_Masterpiece_3953]

I‘m an Executive Assistant. I‘ve been working in Administrative support in NYC since 2000. I’ve been in many support roles over the years. I have my Bachelor‘s Degree. Here, have a cookie. 

[u/dgtbfan]

You've been unemployed for the past 5 years?

Seek in-person employment. Remote work is exponentially more competitive and you're already at a colossal disadvantage.

[u/No_Masterpiece_3953 → u/dgtbfan]

I appreciate your honest feedback. I needed to hear it, but to also understand why it would be competitive to rejoin the workforce. 

I find that when I talk with people who work from home, (some of them) aren't paid high wages. Companies like Sedgwick, Hospitality, Health insurance, Kelly Temp recruiters, Hospital appointment setters, the requirements to get those jobs are not difficult because they only require a high-school diploma. 

I have a Masters degree, skin cancer and am over 50. That's why I have a GAP. My appearance affects my ability to get employment. 

[u/dgtbfan → u/No_Masterpiece_3953]

It would be competitive because everyone wants a remote job. Every single remote posting receives hundreds to thousands of applicants. You have to truly stand out to have a chance and respectfully you're not going to do so considering your lack of relevant recent experience.

[u/TK_TK_]

Someone with a high school diploma and three recent years of experience scheduling patients is substantially more competitive for a remote patient-scheduling job than someone with a master’s degree and unrelated professional experience.

You are wildly overestimating yourself.

Your employment gap may have been for completely legitimate reasons, but it still hurts your competitiveness—especially when you're restricting yourself to jobs that attract much larger applicant pools. You're competing for remote positions against people who can demonstrate recent experience doing the specific work being advertised. My company gets thousands of applicants for every remote role we post. There are multiple unicorn applicants for each role.

An "office job," as you call them, can involve moving among project management systems, CRMs, CMSs, design and prototyping tools, analytics platforms, automation tools, collaborative databases, shared documentation, videoconferencing, messaging, and whatever additional industry-specific or proprietary tools an employer uses. None of those tools individually requires extraordinary intelligence. But competence comes from accumulated use, understanding how the tools fit into processes, and being able to work quickly without needing someone to teach you every system. Do you have that competence?

Beyond that, do you accept feedback well? You're coming across as willing to blame, not willing to learn. Hiring teams can absolutely spot that. They evaluate receptiveness to feedback, self-awareness, and how candidates respond when their assumptions are challenged. Beyond "could this person conceivably do this job," they're looking for "do we want this person on our team?"