Career Paths/Exit Opportunities

On a conference call, so I have plenty of time to answer. If anything, let this be a lesson that a lot of times there isn't a "path"

1. Graduated with a sub-3.0 GPA in Political Science from a shit school you've never heard of because my highschool grades were shit too. Divorced parents, lack of a challenge, laziness, getting As on every test but never doing any homework assignments, etc. - every excuse in the book. Failed out of college at one point because I got mono, took a month and a half off, and showed up asking for what work I missed. Took the LSAT, did well, but realized soon after I didn't want to go to law school. I had a ton of "leadership" positions in college - fraternity president, student government president, university budget council, etc. but little to show for it. Behind the curtain, I was pretty weak. I needed a job yet had no skills outside of being personable, confident, and outgoing. Naturally, I looked toward brokerage.
2. A fraternity brother of mine was an investment sales broker with a name brand firm. I networked in over a 6-month period and got hired as a market analyst.
3. I worked hard and became head market analyst. Wanted to be front office, so got my license and talked to my bosses about it until they promoted me.
4. Ended up being a case of the grass is always greener. The principal I was assigned to was one of the worst professionals and worst people I've ever met. Made my life hell for almost a year. Nevertheless, I got us into a pitch with what would have been the biggest deal our office would ever land due to my relationships. My office took me off the pitch team so I could "focus." My office left the deal. It was the final straw, and I told them I would not be staying with the company past the end of the year, giving my notice, because I would have to go on a draw and I didn't want to be in debt to these people. They fired me on the spot. The principal I was assigned to wasn't even in the room to tell me in person - he had his partners do it.
5. By that time I had been dating a girl long-distance and decided I would just move to where she lived. Got hired by an out of state family office to do multifamily acquisitions, but they had a problem in that their property manager just quit, their lease-up was behind, and if they didn't hit 100% by August they wouldn't for the year because although it wasn't student housing, the building was almost all graduate students. It was a B- asset with A+ location. They said "hey, you know how to lease. I know you've never done this, but could you please lease up this building? Then you can do what you were hired to do." I leased up the building in time, but prices in the market skyrocketed and they lost interest in buying anything else. So, I turned into a full time residential property manager - not exactly my dream or the height of prestige. Company starting giving me shit for not knowing how to be a property manager - go figure.
6. Realizing that neither of my previous two jobs were what I wanted to do at all and neither ended well, I applied to MSRE/MRED programs. Both as a broker and a property manager, I saw who really held the power in the industry - the owners. People I knew in the industry found a lot of success in transitioning to the buy side by going the Masters of Real Estate route and I realized that my resume to date did not reflect my abilities or goals whatsoever. I got in to a number of places, picked the one I thought best fit my goals at the time, and soon after was told I was being let go as a property manager. Alas, the "let me speak to your manager" -esque regional did not like me much. At this point, I had 2 companies on the resume with 2 terminations to show for it.
7. I started looking for pre-MRED internships with the pitch of "I am going to graduate school this fall, so I'd really like to intern with you ahead of time to learn the ropes." Got a full time job offer at a REIT at this point, which I wonder about every time I make a student loan payment. I turned it down because it wasn't development. I needed money during my internship hunt, so I worked as a superintendent with a GC renovating an airport Holiday Inn. If you ever wonder what is behind the wallpaper at old hotels - let me tell you - you don't want to know. Years later this GC would get raided by the federal government for hiring illegals and get in a class action lawsuit for not paying overtime. It was a class organization, let me tell you.
8. Finally, I landed a summer analyst acquisitions position at a family office that was well known in the city I was in. A lot of people assumed I was someone's son or grew up in the richest neighborhood in the city because those are the only people who worked there. Hilarious. Learned an absolute ton that summer, from highbrow stuff like how to underwrite deals to doing low brow due diligence walks at expiring Section 8 properties and finding hoarders, FBI drug stings, pedophiles, and getting hundreds of fleas literally up to my knees.
9. Went to graduate school. Overall, I'd rate it a 6.5/10 experience. My main complaints were that it was very light on finance, geared toward the lowest common denominator (and 1/3 of the class was straight out of undergrad), and taught you more how to be a visionary developer than what you actually do as an associate at a company. Still, I did a summer associate stint at a NMHC top 25 developer, made some truly absurd connections/mentors, and accomplished a lot - won a couple elections, won a couple competitions, got nominated to a regional ULI board, graduated with above a 3.8, etc.
10. After this long and windy road and an iron clad resume I was proud of, I hit the job hunt. Struck out at least 70 times, maybe over 100. Finally got an offer from a prestige firm as an asset manager and a start up development associate. Took the development route and didn't look back. Got promoted to development manager. Been doing this about a year and a half.

Along the way I had to learn how to be a professional, how to channel my strengths, how to care about excelling, how to build a network, and how to mold myself into who I am today. All that said, there are infinitely easier and cheaper ways to do all of this. Proper guidance/mentorship from the start would have helped. Hell, one of the reasons I post so much on this forum, mentor students from my graduate program, and give my opinion as much as I can is to help others who were in my position.

Most people will probably find a middle ground between "the path" and my meandering nonsense. The point is, there are many ways to accomplish what you want to accomplish, and if you keep driving forward and have the necessarily skills and mentality, much is possible.