SUPER long post, need advice S.O.S

Sorry to whoever I directly replied to. This is my first time posting/I recently found this site. I am going to slap my 3rd and final edit here on the main post. 

I have edited the post down from the original 7 pages to just over 2 pages. I know, still heinous. I find I am having a lot of trouble being clear and concise here because I am mind f***ed when it comes to this issue because, well, “emotions”. 

Thank you, seriously, to whoever reads through all of this and gives any input. Even if you think I am a little b*** (which, honestly, would be fair right now of you to assume), I am pretty much begging for any advice or input you could spare.

I am 34 years old and have been at my current position and current firm for 8 years. Before that I was at CBRE for two years and before that I was at a management company for a year (my first job straight out of college).  At CBRE and at the management company I was an asset manager.

I have been working at the direction of a mentor for my entire professional career. My mentor owns the firm I currently work at and have been working at for the last 8 years.

Now let me give you some info on what I do that I think you would require to help me here:

I have been responsible for pretty much everything regarding our portfolio for the last 8 years. Asset and/or portfolio management, acquisitions, (some) development, and ownership (I own some % amounts in a couple of deals, my own 14 unit, and two rental houses).

The main office I work out of consists of  5 to 10 employees, and it is owned by one man (again, my mentor). He owns roughly 3,000 apartments and 2,000 mobile home park pads, and a smattering of about 15 office/retail/industrial properties. The value of the properties averages around 6 million - they are all spread throughout the Midwest. The average rent (rough estimate) is prolly 600 to 800 for the apartments and 150 - 250 for Mhps (don’t own a single trailer only the pads).  Altogether it’s worth a little over 300 million.

Some things to keep in mind: while our office is just 5 employees, we have three management companies that manage our properties. The largest management company we use manages around 10,000 total units. About 3,000 of those units are ours. The owner of my firm owns 2/3rds of this management company. I spend half my time at the headquarters of this management company and half my time at what I would call my “main but smaller” office. When I am at my office at the management company, I am only working on our portfolio.

 I close transactions there, I meet with and instruct contractors there, I direct property managers from there, I do financial analysis there, I make budgets there, I use costar there, meet lenders there, etc – AND I do all those things at our smaller family office as well.


One could say I have been hyper focused on no name markets in bumblef*** Midwest for my entire career.

My biggest deal (ever) has been 15 million dollars and that was ultra rare. Usually, the deals I source and then take on the asset management for, are about six to eight mil in value.

I am moving to one of the top five largest cities in the US, so, combined with it being the worst time ever to be looking for a job in my lifetime, I am pretty sure I am going to be utterly fudged. Because two or three deals in this city = the value of our entire portfolio of 70 + properties. Even the family office, or whatever you would classify my office as where I work now, whatever the equivalent would be in the city I am moving to -I am certain their deals would dwarf all of mine in value.

I am at a total loss as to what to do. I don’t want to shoot myself in the foot in anyway in making my transition to the new city and the job search that it is going to entail. I am totally comfortable in my market and in what I do, but I am terrified it won’t translate to a massive city very well, if at all. I sometimes get so anxious I consider drastically completely switching to becoming an appraiser or something, just so I can at least not be unemployed. Which I fear I will soon be. I then cry. For hours.

So, now that you have some info on my situation and are aware of some of my particular concerns, I have a few questions regarding the situation.

First off, what would you classify the firm I work at with my mentor. Am I correct in assuming family office? I haven’t been reading these forums for too long and I am curious as to what most here think about this.

Also, I wanted opinions on when applying, which company do you think would be better to say I am applying from? The company that I currently work for and have been for the last 8 years (with my mentor) or the management company?

(Neither would be sketchy or dishonest in the slightest. I work side by side with the principals of both and they would attest to this in any references.)

The reason I am asking this is because I feel like it would be silly to apply for a “director of asset management” position and put my current position down as the “director of asset management”, as the office I spend half my time at does not have departments or directors.

That being said, the management company that we use, and own 2/3rds of, and that I spend the other half of my time working at DOES have departments and directors of property management etc.

So, to summarize: would it be dumb to use director for anything given my aforementioned work set up? At my main smaller office, it seems silly. There are no departments or directors. There are no VPs. There is me, the principal, 2 attorneys who work for him full time, and a couple receptionists. But where I spend the other half of my time, at the management company, there absolutely are all of these departments and positions. The principals at both my main smaller office, and at the management company would verify whatever came their way with regard to references.

I have some more questions and concerns. I know context is very important here, so I am trying to provide details without being too lengthy.

I am planning on staying as Multifamily based as possible.

Can I apply to institutional places for asset management and acquisitions positions or will they insta reject me?

Are there positions outside of asset management and acquisitions that you think I should look into? Which leads to my last and final issue that I would kill for some input on. That is: roles as an MD.

Regarding said roles:

I feel like when I apply to places, especially larger places, they are going to take one look at me and say “lol this dumb bich thinks she’s an MD at 34".

And if they deign to take a closer look, they'll say "oh, okay, yea, an MD at this weak @ss little hick family office in bumblef*** Midwest".

I have zero concern (whatsoever) explaining and/or justifying anything in an interview with an actual person. But I am concerned it won't even get to an interview because of things like this. And because I feel like applying through anything other than a human in an actual network is greatly frowned upon for my advanced age. But I have ZERO contacts in the city I am moving to. Honestly, it makes me feel like such a worthless f***ing joke. I have felt this way since turning 30.

Does anyone in their 30s even get jobs through LinkedIn, indeed, and company websites?

I mean, as you can tell from this disjointed wall of text, I am freaking out. I feel as though I would have figured out a lot of these things in my 20s if I was applying under the same conditions as most people in their 20s. But I had a mentor, so I was able to bypass a lot of that. That leaves me feeling awkward AF for having to ask a lot of these things. At the same time, I believe I have a ton of valuable experience due to my mentor, and even a valuable resume, but I have no idea if I can possibly convey this due to the shitload of reasons and concerns I have gone through here.

Thanks again and God bless anyone who provides any input.


I copied and pasted this on Word -- 7 pages and 3k+ words. It seems like you are going through some stuff. People here can be helpful sounding boards, but they are also busy people. It might help if you read through your post again, and have something like a TLDR of max 7 bullets or something. I'm not trying to sound like a douche, genuinely trying to give feedback to you so that people will be more likely to respond to you.


Don't over inflate your title. Pick something that makes sense for your experience. If you call yourself an MD and are applying for VP spots, you will almost immediately get passed on because someone will think you were really an MD and they can't hire that high/expensive. 

Otherwise, speak with as many people in the new market as you can. Contacts/networking matters.


There's a gentleman they call the "Strip Mall Guy" who is offering prestigious roles with top of market and you shall find him. 

Most Helpful

This is pretty chaotic, restructured the ask below for those wanting to offer this guy advice. My 2c is don't be shy, move to the bigger market, focus on the work you did and not the title, don't sweat your age. Apply for roles maybe one level below where you are title-wise, people will understand your desire to transition, and should promote you fairly quickly if you demonstrate your skillset. No matter your recruiting approach, it's going to be hard no matter your background. So settle in for 3-4 months of hard outreach, networking, applications, etc, keep your leads high, and you'll start to get opportunities. Also don't underate your deal experience, focus on what you know well and highlight that, don't be arrogant, but don't be too humble either, you need to show that you belong.


  • 34 years old, been at the current firm for 8 years, previously at CBRE and a management company.
  • Specialized in asset and portfolio management, acquisitions, development, and ownership.
  • Mentor owns the current firm and has been guiding the career.

Current Situation:

  • Manages a portfolio of around 3,000 apartments, 2,000 mobile home park pads, and various other properties in the Midwest, valued at over $300 million.
  • Works between a small family office (5-10 employees) and a management company with three departments.
  • Concerns about transitioning from a smaller market to one of the top five largest cities in the US.

Specific Concerns:

  1. Unsure of how to classify the current firm—questions if it is a family office.
  2. Which company to mention when applying—current firm or the management company.
  3. Title concerns—wonders if using "director" is appropriate given the structure of the smaller office.
  4. Interested in staying in multifamily but unsure if applying to institutional places is feasible.
  5. Considering roles as an MD (Managing Director) but concerned about being taken seriously.

Major Fears:

  • Worries about being rejected due to the perception of coming from a smaller firm in the Midwest.
  • Concerns about age (in 30s) affecting the application process.
  • Doubts about the efficacy of using LinkedIn, Indeed, and company websites for job searches.

Request for Advice:

  • Seeks guidance on classifying the firm, choosing the right company name when applying, using titles like "director," applying to institutional places, exploring roles as an MD, and overcoming age-related challenges.

Overall Advice Needed:

  • The person is looking for guidance on navigating a major career transition, especially in terms of how to present their experience and skills effectively in a new and more competitive market. They are worried about potential bias related to their background, age, and the transition from a smaller market to a larger city.

There's nothing you can say to a contact that will magically make them refer you for a job. Once you've touched base with them, either they know of an opportunity now, or they'll think of your name when they do hear something. The one exception is if they are connected with someone you want to talk to, you can find a way to craft an ask to make the intro. Ultimately, your best bet is to keep looking and making new connections. If you want to keep your name top of mind for them, you can share useful things with them every month or two, like a relevant article, or some resource. You can also come to them with a question about the industry, or ask them for advice around a specific situation, and if they like you they might give you some good feedback.


Your post is long - but here is my advice - hell yes I get/have gotten jobs/interviews/job offers from LinkedIn. All the damn time. Ask your mentor for advice about how to handle the resume. I’m assuming it’s no secret you are moving and if you’ve been a solid employee they should help you out. 

Like the unadjusted- only with a little bit extra.

Not in real estate, but will try to help anyway.

One big thing you have left out of your (re-summarized) post is why you are relocating.

The most logical thing I can think of would be family reasons (i.e., spouse got a new job and you made the decision to go with).  Feel free to correct me if I'm wrong.  Hopefully in that case, unemployment is not a "fear of financial insecurity" issue, but more "all my hard work has gone down the drain and I am starting over".  The latter is a very natural fear, but that does not mean it will come true.  If it's the former, then your story is going to be harder to explain to a future employer.  i.e. - Why did you leave a stable, well-paying career to move across the country with nothing lined up at risk of not being able to pay for rent & groceries? 

If you want to pivot from "small, entrepreneurial family office" into "institutional real estate", that's fine, but that's also a change.  So now you're making two pivots (location and career path).  It's not impossible to get a job through blind applications / LinkedIn.  But that fact pattern will make it very tough for you to get through HR filters and get an interview.  Especially if they assume you want them to pay your re-lo.

The good news is, it sounds like you have developed a lot of skills, work hard, are a self-starter, etc.  You can add value, it will just take some elbow grease to find the right opportunity.  If you want to find a role more like the one you already have/had, you sound like a great candidate.  Just because you're in a top 5 metro doesn't mean you need to work on 50 story projects.  All these metros have exurbs.  You will need to learn some new geography, but can apply your experience.  Good people are incredibly difficult to find in less institutional workplaces.  Of course finding your new seat will also be a bit tricky, as these places are small, private, and don't have "HR" when the firm has a single digit number of employees.

This is where the networking comes in.

Hopefully you left your mentor on good terms and he is a great reference for you.  You may not know people in your new market, but push yourself to find people in your existing work network who do.  (i.e. - you used to work at CBRE, well do your old colleagues know anyone in your new market?  Same goes for the contractors, property managers, appraisers, attorneys you currently work with.  Somebody knows someone in your new market.  If they think you're good, and they have a soul, they'll introduce you.  Have coffee (or a zoom call if you're not relocated yet).  Project confidence.  Don't beg for a job, but ask good questions about your new market.  Pretty soon you'll start feeling better.  Stick with it and something will pop up.  But you may need to be patient to find something good in a tough market.  Hopefully you accepted that as a part of your decision to relocate in the first place and that's not a surprise. 

I appreciate that its stressful out there right now.  But lots of good, smart, hardworking people take lumps that aren't fair or get hit with a cycle by being in the wrong place at the wrong time.  Then they dust themselves off, get back to work and bounce back.  Careers are long and non-linear.


No, DEF not following a boyfriend or SO of any kind. It was in my original novel of a post. I will try to summarize why I need to move:

I currently live and work where I do because when I was 23 years old and had just graduated college, a mentor offered me the opportunity to come and work for him.

If I agreed to work for him until I was 30 years old, he guaranteed I would acquire X amount of property, X amount of net worth, and learn X number of things.

He warned that I would do what he did when he was my age – work 7 days a week from 6 am to midnight. He said he was aware I had no friends and no family in his state and that if that bothered me to forget it – because I would have no social life anyways. All I would do is work. He said if I expected to be the stereotypical entitled millennial, I was very wrong, and he would fire me with no hesitation.

To me this was the deal of a lifetime.

I have friends and family in my state. I could care less about anything other than success in my career and owning my own little portfolio.

Fast forward to now: I have everything I need and that he promised I would get. Though I won’t get a dollar of the passive income until my late 40s as all the property I acquired I did so in my twenties and early thirties, so I had to use a lot of debt. Debt that would not have been possible without his relationships with the lenders that gave it to me. I will never have to worry about the management of properties whatsoever. I haven't since I bought them, and I never will need to.

But so yea that’s why I need to move back to where I am from. I initially planned on staying here at the max until 30 years old. I am now 34.

Also, its complicated, but my brother has cancer again. He got it when I was 25 and it was way worse then. He had it for a few years. Beat it. Was in remission for over 5 years. And it has just resurfaced. Detection is ten timers earlier this time and we know he will be fine, and this will be nothing like the first time (one of my parents is a very good doctor). Still though, most likely will need radiation and chemo again, and I can’t handle the driving between states like I did the years he was sick.

There is no spouse or significant other at all. There hasn’t been one in years. I am pretty sure that I may have just ensured that I lose out on that part of life forever. So, all I have is my career. If I lost out on that I would really have zero reason to live. 


I am sorry about your brother.  Though that is great that it sounds like you're confident he will ultimately be okay.

You are seeking to relocate for family reasons.  More specifically, you desire to return to the metro where you grew up / your family of origin resides.  You were willing to go wherever necessary to advance your career starting out, but this has always been the long term plan.  Framing it this way sounds perfectly logical and reliable (which is the way you need to sound in order to get hired).  You may or may not choose to disclose that it has become more urgent for you, because of a family health issue.

Separately, this is 2023.  Are you sure that you need to change jobs?  Many people negotiate hybrid work arrangements.  It sounds like you will be tough to replace.  The drive may be tough, but what if it was once a month instead of four times, etc.  Is it better to fly? Etc.  Even if you do decide to move on, it sounds like you can afford to be somewhat patient with your timeline here (i.e. - don't quit & create false urgency), even if emotionally you feel a strong need to do this.  Let that drive you to network.

It sounds like you've built up some nice equity, but you don't really value it because it's not cash flowing right now (all going to debt service), and there is some one-third life crisis type of angst in there.  Did you make the right choices for the last decade, sacrificing personal for professional gain?  That is something MANY if not MOST of the posters on this board CAN relate to.  Well you can't undo the past now.  But I think you can take pride in what you've accomplished and thoughtfully and intentionally take steps towards realizing the future that you want for yourself.  Just keep your composure and I'm sure you'll do fine.  Good luck.


Also, I don't think I mentioned, I have a master's in real estate from a small private school. I know many view the worth of a masters via its networking, of which this masters provided me none as it was a small program and part time. But it might be worth mentioning, though I doubt it. 


Ok first things first, I know people who are older than you find their love of their life. I know people who've found people at 60+, just because it hasn't happened right now doesn't mean it will never happen. 

Second, you need to find a reason to live beyond work, that's incredible unhealthy. That's a whole separate post but suffice it to say it sounds like you need a bit of a breather to figure some personal stuff out. It sounds like you're fine financially and are well set up with assets to keep you secure for the foreseeable future, which is great, now you can take some time to think about what else you want in life. 

Third, just because your deal sizes are dwarfed by big city deals it doesn't mean the experience wasn't useful. For the most part the steps are the same for a $5m or $250m deal (yes, I know there are different levels of complexity as deal sizes go up, but in terms of being a useful employee doing 100 $5m deals is more valuable than doing one $500m deal). Go out there and start talking to people, connect on LinkedIn and get coffees, apply to jobs (I've gotten two jobs from LinkedIn, and even more interviews), get a feel for the city, collect your thoughts and resume. You sound like you can clearly perform, it's now just a matter of adapting to a new environment. 


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