Advice on choosing my "day job"

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Advice on choosing my "day job"

Fisher Morton
New to Real Estate · Charlottesville, VA · Member since 2025 · 1 post · 0 votes

Hi everyone,

Long-time lurker, first-time poster. I’m a huge fan of BiggerPockets and am hoping to buy my first rental property within the next year or two. I’m stuck between two very different career paths and would appreciate some advice from people who have been in the industry.

Job 1: High-paying role outside of real estate

Pros:

  • - High income potential; I could realistically save ~$60K–$100K within two years.
  • - More personal capital to put toward my first investment properties.

Cons:

  • - Completely unrelated to real estate or investing.
  • - Very demanding hours, leaving little time to learn the industry or actively search for deals.
  • - I would likely need to rely heavily on brokers and turnkey providers because I wouldn’t have the time or experience to thoroughly analyze deals myself.

Job 2: Multifamily real estate development role with a large institutional company

Pros:

  • - Direct exposure to the real estate industry, specifically multifamily development.
  • - Opportunity to learn underwriting, deal structure, construction, financing, and the development process from experienced professionals.
  • - Build credibility and relationships that could help me later when raising capital or working with lenders.
  • - I’m genuinely interested in the day-to-day work and could see myself building a career in this space.

Cons:

  • - While it pays well, I would likely only save around $50K over two years.
  • - Less personal capital available to invest immediately.

The way I see it, Job 1 gives me more money to invest but less knowledge and fewer connections. Job 2 gives me the knowledge, experience, and network but delays how much capital I can put into my own deals.

For those who have built a real estate portfolio or transitioned into development, which path would you choose? Is the industry experience worth sacrificing some initial investment capital?

Thanks in advance for any advice.

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Janice Carter
Real Estate Broker · Atlanta · Member since 2024 · 1k+ posts · 606 votes
2mo

@Fisher Morton I would lean toward Job 2 because it aligns with your long-term goals. That said, there are many ways to learn real estate investing besides on the job experience. In addition to the BP community, you can learn through local REIA groups, books, podcasts, mentors and by analyzing deals yourself. If you are disciplined about your investing education,
you can learn while earning a strong income.

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  • Ricardo Gonzalez
    Property Manager · Orlando, FL · Member since 2026 · 22 posts · 18 votes
    2mo

    This one hits close to home because I'm essentially living Job 1 right now. I currently have an unrelated, high paying job while building a property management company on the side. So I can give you a real answer rather than a theoretical one.

    My honest take is that capital is easier to replace than knowledge and network. The extra amount in savings means nothing if you buy the wrong deal because you didn't know what to look for. Less in savings but with real underwriting experience and relationships with lenders and developers is worth significantly more at the starting line.

    That said, the thing about Job 1 is that high income buys you optionality. With $60K to $100K saved in two years you can afford to make a mistake on your first deal and recover. With $50K and no margin for error, one bad deal can set you back years.

    The real question is what kind of investor you want to be. If your goal is large multifamily, development, or raising capital from others someday, Job 2 is almost unfair in how much it accelerates that path. You'd be learning institutional underwriting and deal structure from the inside, the kind of education that normally costs years of trial and error.

    If your goal is smaller residential, SFR, or small multifamily, Job 1 probably wins because the knowledge gap is smaller and capital matters more.

    One thing I'd push back on in your framing though: Job 1 doesn't have to mean zero learning. I've spent nights and weekends reading, analyzing deals, and building my business while keeping the W2. It's harder but it's very doable. The demanding hours are real but so is the discipline you build from having to be intentional with your time.

    What does your end goal actually look like in 10 years? That probably points directly at which path makes more sense.

    1Reply
  • Janice Carter
    Real Estate Broker · Atlanta · Member since 2024 · 1k+ posts · 606 votes
    2mo

    @Fisher Morton I would lean toward Job 2 because it aligns with your long-term goals. That said, there are many ways to learn real estate investing besides on the job experience. In addition to the BP community, you can learn through local REIA groups, books, podcasts, mentors and by analyzing deals yourself. If you are disciplined about your investing education,
    you can learn while earning a strong income.

    2Reply
  • Megan Mulligan
    Member since 2026 · 4 posts · 0 votes
    2mo

    There's a lot that's going to matter here, but your personal time and mental state are critical, so let's start there: can you actually be happy for the next two years in a job you're not passionate about, or will it crush your soul? I can't oversell this — if you'd be dreading it every day, it's not worth it no matter what the math says.

    Now the specifics. First, timing: how long would it realistically take you to land either job? If they're roughly the same, this part's a wash. But worth noting — hiring usually slows in Q4 since companies are focused on getting existing employees through the holidays (less bandwidth for onboarding), and budgets for new roles often don't get approved until early Q1. So there could be a real timing gap depending on which one you can actually land faster.

    Then there's time value of money. Job 1 gets you $60-100K in hand after two years, Job 2 gets you $50K. That's a real gap, but it's not the whole picture — Job 2 is also handing you underwriting, deal structure, financing, and construction experience most people pay years of trial-and-error (and real losses) to learn on their own. The question isn't just "which gets me investing sooner," it's "which path gets me investing well, sooner." Doing your first few deals with zero industry background usually means leaning hard on brokers and turnkey providers — and that comes with its own cost, not just risk.

    I know that's not a decisive answer, but the real question is: could you genuinely stomach either path? Once you know that, it comes down to risk tolerance. Most real estate investors I know lean risk-on, so if you can handle the slower capital build, I'd lean toward Job 2 — the network and skills tend to compound faster than people expect, and they make every future deal cheaper and safer.

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  • Jeff Roth
    Real Estate Consultant · Ann Arbor, MI · Member since 2022 · 465 posts · 255 votes
    2mo

    Hi Fisher from Charlottesville, VA-

    Great question! You see yourself building a real estate portfolio and doing real estate development and are torn between two work options currently.

    One is high paying away from real estate with potentially demanding hours but would allow you to save more money. The other is in real estate with potentially less pay but more industry contacts and experience with multifamily development.

    You wonder what might be the better choice for your long-term goals.

    I think either could work and you might meet other potential partners who would be happy to put their money to work in your deals making the need to save more of your own money less important.

    You may also learn what you like and don't like about multifamily development by taking a job there more than taking a job that allows you to save more of your personal money to do deals.

    To Your Success!

    0Reply
  • Jacob St. MartinPro Member
    Investor · Charlottesville Virginia · Member since 2021 · 348 posts · 346 votes
    2mo

    Hey Fisher, 

    I am a local realtor and real estate investor. I would ask the following questions - why do you want to invest in real estate? What type of real estate interests you? Would you still be reasonably happy/satisfied in job1?

    If you think you'd be miserable in job 1 then to me it is a no brainer. I started real estate investing as a grad student and was miserable in my program, I only made it about two years before I quit to do real estate full time. 

    Assuming both jobs are still on the table after you answer that questions, what type of real estate interests you? If you are interested in single family, flipping, short term rentals, etc. then working for a multifamily developer may not teach you as much as you'd like. If you are interested in multifamily development then I'd definitely go that path. 

    The last question is, why do you want to invest in real estate? For most people the answer is a combination of financial freedom and interest. But narrowing down on a very specific goal will help you determine what type of real estate would work best for you. Assuming that you don't mind job 1 and that you don't feel particularly strong about multifamily development, I might actually go with job 1 and then work on getting you your first rental ASAP. 

    Personally I think house hacking is the best way to start out and since the capital requirements of house hacking are so low you could potentially even start now or much sooner than you think. Feel free to reach out if you want to talk more! I'd love to grab coffee or something. 

    0Reply
  • Travis TimmonsPro Member
    Rental Property Investor · Ellsworth, ME · Member since 2021 · 1k+ posts · 2k+ votes
    2mo

    Job 1 plus an owner occupied strategy is what I would do. Whether you do a live in flip or proper house hack, owner occupied is lower risk, has a longer timeline, and protects you a bit more from buying bad deal bc you have to live there. You know the local market and where people want to live. 

    Make more money assuming that you don't hate job 1, pile up cash, get a "training wheels" property that you live in, and start the snowball rolling down the hill. 

    2Reply
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