Should I include this in my resume?

[undercover]

Nearly 28, graduated in 2014 (mix of community college + online university while working full time and doing side work which is why it took 6 years). I haven't held an actual job in about 2.5 years. My degree is in Management Information Systems and I've never held a job directly related to my field or what I actually want to do. Reasons for this are noted below.

I've applied for several jobs lately but only got an interview for one and even after it seemingly went well, I never got a call back. I need to change my approach obviously. Basically, for the past two years I've been focusing on my rentals full time - though, I guess "focusing" isn't the proper verb. I spend maybe 1 hour a week actually working. But still, I've built two successful vacation rentals that more than pay for all of my expenses + extensive savings. I'm semi-FI which is why I'm very reluctant to take on employment as it is (I've been selectively applying). But I'm also worried that I'll never break into a career that I like. At heart, I crave risk, change, and excitement, so I never see myself as a "careerist" but I want to have it as a backup while I build my business.

So - to the question: should I include "real estate investor/entrepreneur" on my resume? I'm definitely going to be asked about my intermission between now and my last traditional job, but will employers care that I've ostensibly built a business?

Or is it just too little too late for me? I've had a very rough last couple of years mentally/physically which is why I haven't been focusing heavily on applying and trying to build an inkling of a career. Last year was an unproductive mess for me and I basically became a slob. I'm trying to get back into the groove of things. I'm just worried that I've waited too long.

[Off the Wheel]

Yes, include it, but framed in a way that relates to whatever you're applying for. Knowing nothing about your field, some relevant skills/spin from your real estate business could be:

Developed a successful small business based in the vacation rentals market. Identified market opportunities, managed the investment, performed/hired/assigned work as needed to develop residence to appropriate standard, built out property listings and managed booking flow, developed marketing and communications strategy to secure 100% occupancy rate... yadda, yadda.

Another option would be to speak candidly to developing a successful and profitable business model in rentals that allowed you to spend time on <x thing that is still relatable to the y job you're applying for.> IE learning languages, developing your skills in CSS?photography/content creation/sysadmin/whatever.

The point of a resume is to get the interview. Recruiters or hiring managers will likely see a hundred plus resumes, long list 20, phone screen 10, and bring in a handful for an interview. Make sure you make it to the phone screen by being interesting sounding and demonstrating capabilities relevant to the job, and don't give off huge red flags (like seeming lazy/"out of work" for 2+ years.)

[marty998]

I would not include it. Hiring managers look for people who can be 100% focused on the job. If you make this out to be a side-business in rentals they are going to ask themselves "who is this person going to dedicate their time to during the day?"

If it's only one hour a day then it's really not significant enough. Tens of millions of people would qualify under that definition of being a "real estate investor/entrepreneur".

You just need a foot in the door. If I were you I'd look for an alternative entry in, not so much the mailroom/admin, but something really junior.

Even if it's mindnumbingly boring with low pay, do it for a year, prove yourself and transfer internally - much easier to do when you're already in.

I went through a lot of low paying accounting training type jobs building a track record over 3-4 year before really getting started in my career and applying for a "good one". Employers loved that I had a variety of experiences, and that I was flexible to adapt as required. I'd suggest it would be good for you to take that path too.

[civil4life]

I would include it.

It shows initiative, hardwork, etc.

I do not think they would think it takes away from your other potential work.

You may consider having someone critique your resume in general.

Do not be afraid to cold call or email a company directly as long as the advertisement specifically says not to do it.

Since it seems that income is not an issue would it be possible to do an internship to get your foot in the door somewhere?

[Meesh]

Normally I would say no, for the reasons listed above, but one of the biggest things recruiters look at is big gaps like 2 and a half years. I would put it on, you can pose it as your main "job" and is now no longer a gap. It explains what you have been doing lately without needing to speak to anyone. Obviously during an interview it could come up, but your resume is the decider for the interviews in the first place.

The goal of the resume is to pass the screening test. Recruiters average about 6 seconds per resume. So if they see big question marks they will just move to the next one. To complicated and it gets a pass (why normally I'd say no to side hustles on a resume), big gaps, too many short time jobs etc.

Not that you asked, but resumes should be 1 page and ideally bullet pointed and chronological, which makes them easier to read and to the point. You get more bang for your buck in those 6 seconds if there is less but more important content. And make it easy to understand, don't forget recruiters rarely know what is actually needed for the job or its lingo, they just have a general idea of it.

Also just be aware that recruiting is a numbers game with 100s and sometime 1000s of resumes now that everything is online. It's totally fine to be picky about where you work, but I would actually recommend reversing tactics. Apply for anything in your field (whether "qualified" or not, sometimes they are desperate for anyone), you'll get more interviews and more offers. Then get picky. Do I really want this job? When they ask for how much are you hoping to make, make it outrageous, if they want you they will counter anyway. Since you are semi-FI use it to your advantage, you do not need to settle and I'm guessing not worried about a time frame to get a job.  This is the best part about having F you money. DH turned down 2 or 3 offers before he found the perfect job with this strategy and resume style. It took longer but it was well worth it.

Good luck!

[Acastus]

Include it to fill the gap in your work record, and show your entrepreneurial spirit. Think through your answer to the likely question, will this interfere with your job here? Your answer needs to be no, though you can include some buts.