Career Crossroads: 3 years of rejection letters, time to take a hint or keep at it?

I am currently at a career cross roads as I have been trying to break into Investment Banking for what seems like close to 3 years now and I feel like I am not making any progress.

My Background:
* Graduated from a Pac 12 school (none of the prestigious California ones) with a finance degree and a 3.6 GPA.
* Part time job as a research assistant for the University while in school. Also had a summer internship doing accounting work for a pharmaceutical company ranked in the top 150 on the Fortune 500 list.
* Coming out of school was getting the typical "thanks, but no thanks" rejection emails/ resume would go straight to the shredder. Didn't have any personal connections in IB to leverage so I thought my best bet would be to take a position in the finance industry to try and build relevancy and work in a city thats close to IB firms. Accepted an offer out of school at a wirehouse and moved to SF.
* Worked at that firm for 1.5 years doing phone sales (not ideal), but finished strong with good numbers to at least show that I am a hard worker. Fielded a call from an MD at a JPM to work in their PW department, hadn't been getting any traction with sending my resume everywhere for IB so I figured taking the job would at least add a big name and they'd pay for me to obtain my Series 7, 63, and 65 licenses.

Most recent IB opportunity:
FINALLY, an opportunity came up when an internal recruiter recommended I apply to their Junior Analyst role (meant for recent college grads or people with 3 years of experience or less). Passed the first few rounds but unfortunately, I was not asked to come in for a Super Day interview. Thought I did well and as an employee applying to an external role I'd at least get an invite but I saw on another forum that there were other JPM employees who applied and were passed over and not invited for the Superday. I get that there were likely some talented individuals outside the firm that applied to the role but at the same it still sucks that your own firm wasn't even interested in an in person interview.

Post Rejection:

I am left with this "now what" feeling. I see myself as an analytical person, I believe that I am smart enough and the skills and work experience I have built along the way would actually be relevant. IB is what I want to do but if I'm being realistic I have had very few opportunities thus far, I don't see any evidence as to why that will all the sudden turn around. SF is expensive and I have bills to pay and in my current role as a FA I'd have to keep working very hard for at lease another year for my book of clients to finally start paying me out. And even then if an IB role does come up, I would have labored hard for 2+ years barely getting paid and then handing the book off to someone else.... Do I give up on the IB dream?

I see my options as follow:

1) Continue role at current company and applying to other IB roles hoping that something works out.
2) Continue role at current company. Build that into a career and not actually like what I am doing.
3) Leave and go to tech where the money is easy and where all my SF friends are.
4) Leave and go to tech where the money is easy, save up money and study for the GMAT and attempt to get in to a Wharton in SF, USF, Berkley, or Stanford MBA programs. Rebrand self and try and jump into IB/PE/VC then. (***Based on my current work history, it seems that the only positions I could be qualified for in tech are sales/ client relationship management).
5) Continue role at current company but apply to 2018 IB Summer internships. Swallow my pride and try and earn a spot on an IB team via this route. (Biggest risks I see with this is 1: Getting an internship and not receiving an offer. Would have no income to pay the bills by summer's end and my resume would feature 3 different roles in 3 years with the most recent role being an internship...doesn't sound ideal to the next company I'd be interviewing with)

I'm sure I'm not the only person on this site to be at this point in their career. Would really appreciate any feedback, especially if you live in SF

 

If it is really money motivated (as the OP seems), then getting into a solid B school would work out great for him. I think getting a solid GMAT and two-three years of good work experience is needed as well.

OP, I don't think tech is not easy money. You are looking at close to 55-65/ish hours a week, but are you saying that you will work in a FA capacity or Project-type role?

No pain no game.
 

Sorry, I probably should have phrased it better rather than say “easy money” for tech. The consensus here in SF is there are a ton of funded companies that are willing to throw around more money as well as a cushier work-life balance with the typical tech perks (catered meals, happy hours, more laid back environment, shares of your firm which you hope will be acquired or go public).

And yes I am currently working in an FA capacity. I’m trying to transition into IB but I’m not getting any traction. I’d think my best bet is to find a boutique or mid market firm in SF, any tips on contacting those firms other than just sending blind resumes or LinkedIn DMs?

 
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