Am I too late to the game?

Am I too late to the game?

New to Real Estate · Member since 2020 · 5 posts · 5 votes

I could use some honest advice. I'm 54 with a W-2 job at a non-profit organization and I honestly love my job and people I work with and for. I've spent the greater part of the past 5 years learning and educating myself in all things RE and investment. I've read all the books and listen to podcasts, as well as constantly scouring all the listings. I joined my local REI group, NCREIA a few months ago and it's been helpful in my RE education and caché. I have a fairly good idea of a strategy and ideal locations.

Here's my issue or at least the biggest. My husband is highly risk-averse. My risk tolerance is a little more moderate. He is also looking to retire in 5 years and has no desire to take on any debt - good or bad, nor does he have any desire to be a landlord or property manager. He is onboard as long as any investments we might entertain is financially feasible and that our assets might be protected from lawsuits. I want to be able to figure out how I might be able to invest in RE on my own - using my own income or LLC. I'm not at all deterred. I'm an AF veteran and so I have VA entitlement. I have great credit and a modest savings. I would, however, prefer to use OPM if that's still a thing.

If it's helpful, here's my why's. RE has been so fun and exciting to learn and follow even though I haven't even dipped my toe in! I want to be able to use all the knowledge I've garnered from my reading and research, podcasts, blogs, and relationships. I'm not ready to retire but when I am, I would love to be able to semi-retire/transition to RE investment and be able to add this as a means of wealth generation for our 2 kids. Additionally, it would be a way to help provide housing for people.

Thanks in advance for anyone willing to chime in.

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Ned CareyPro Member
Moderator
Investor · Baltimore, MD · Member since 2008 · 17k+ posts · 13k+ votes
1y

@Janet Anthony generally investments considered "Risky" like stocks and Real estate, tend to be risky short run  but less risky long run. Keep in mind once you retire you may stilll live another 30 years. That makes you a long term investor. 

Regarding Real estate and risk, most people will disagree with m y next statement But   .   .   .  Real estate is the riskiest investment you can make.  The really important thing to understand about real estate is you get to control your risk. The more knowledge you have the less risky it is.  Follow people like @Jay Hinrichs, @Don Konipol, @Joe Villeneuve, @Chris Seveney and many other here you will learn about the risks and how to avoid them. 

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  • Peter MckernanBusiness Member
    Residential Real Estate Agent · Irvine, CA · Member since 2013 · 2k+ posts · 1k+ votes
    1y

    First off thank you for your service! The person that comes to mind after reading this is Dave Ramsey, not about investing with no debt. He talks about getting your spouse on board with savings, paying down debt etc. This is the same thing, you need to get your husband on board, and make sure he is good with everything to be able to have a great relationship now and going forward. I would really get him on board by whatever way is good for him, going to conferences, meetups, reading books and more with you. Being able to share in the experience is the best and be able to lift each other up through the process is the best thing that would set you both up for success going forward. 

    The McKernan Group4.957 Reviews
  • Michael K GallagherBusiness Member
    Real Estate Agent · Columbus OH · Member since 2018 · 1k+ posts · 1k+ votes
    1y

    @Janet Anthony it sounds like you are interested mostly in actually owning the hard asset which is great but that is generally the most "active" form of investment. But if that's the way you would like to go then the lowest risk is going to be a newer or newly remodeled asset in a generally good area, that maybe has some appreciation in the 10-20 year time frame. Selecting your market will be interesting as I'm sure you have insights into the military and those types of housing arrangements so perhaps a niche there to tap into based on your existing expertise....but regardless to address your question you are not too late, and investing is a spectrum, ranging from flipping to buying stocks in a REIT, and it all works, just depends on your preferences and style really.

  • Real Estate Agent · Kansas City · Member since 2018 · 4k+ posts · 3k+ votes
    1y

    I would get your spouse on board or make sure he is OK with getting into investing. Not a good idea to do your own thing when you're married, can lead to issues. With having VA I would target a 2-4 unit place to get your feet wet. From there save and invest again. Every investment has pros or cons to it. Stocks can rise and fall. Real estate the same. If you make smart buys, have reserves and do your due diligence you will mitigate the risks. I would make detailed plans and examples to showcase your husband. Show him actual data and see where his head is at.

  • Andrew SyriosPro Member
    Moderator
    Residential Real Estate Investor · Kansas City, MO · Member since 2014 · 10k+ posts · 5k+ votes
    1y

    With regards to age, absolutely not. My dad didn't really get started until he was 45 and within 10 years, he had a very successful real estate company. It doesn't sound like you're trying to build an empire, so absolutely it's not too late. Although that being said, it is a very tricky market with rates high, prices high and inventory rising. 

  • New to Real Estate · Member since 2020 · 5 posts · 5 votes
    1y

    @Peter Mckernan thanks for the advice and well wishes. I am and have been working hard to get him onboard with RE. I agree with you. It would be fun to be able to do together but it hasn't been easy. I persist and I see small changes in mindset so I think we're trending in the right direction.

    @Michael K Gallagher also thank you for your feedback. The strategies that I think would be reasonable as a newbie are long term rentals of small to medium sized SFH that don't need much work or turnkeys. I'm looking to start here in my own backyard here in Raleigh and Charlotte.I am currently looking at the VA's one-time closing. Thanks again!

  • Ned CareyPro Member
    Moderator
    Investor · Baltimore, MD · Member since 2008 · 17k+ posts · 13k+ votes
    1y

    @Janet Anthony generally investments considered "Risky" like stocks and Real estate, tend to be risky short run  but less risky long run. Keep in mind once you retire you may stilll live another 30 years. That makes you a long term investor. 

    Regarding Real estate and risk, most people will disagree with m y next statement But   .   .   .  Real estate is the riskiest investment you can make.  The really important thing to understand about real estate is you get to control your risk. The more knowledge you have the less risky it is.  Follow people like @Jay Hinrichs, @Don Konipol, @Joe Villeneuve, @Chris Seveney and many other here you will learn about the risks and how to avoid them. 

    • Don KonipolBusiness Member
      Investor · The Woodlands TX / Avon, CT · Member since 2009 · 6k+ posts · 10k+ votes
      1y
      Quote from @Ned Carey:

      @Janet Anthony generally investments considered "Risky" like stocks and Real estate, tend to be risky short run  but less risky long run. Keep in mind once you retire you may stilll live another 30 years. That makes you a long term investor. 

      Regarding Real estate and risk, most people will disagree with m y next statement But   .   .   .  Real estate is the riskiest investment you can make.  The really important thing to understand about real estate is you get to control your risk. The more knowledge you have the less risky it is.  Follow people like @Jay Hinrichs, @Don Konipol, @Joe Villeneuve, @Chris Seveney and many other here you will learn about the risks and how to avoid them. 

      “Real estate is the riskiest investment you can make. The really important thing to understand about real estate is you get to control your risk. The more knowledge you have the less risky it is. ”

      Ned, this is one of the most insightful statements I’ve seen in along time.  
      Private Mortgage Financing Partners, LLC
    • Joe VilleneuvePro Member
      Plymouth, MI · Member since 2013 · 13k+ posts · 19k+ votes
      1y
      Quote from @Ned Carey:

      @Janet Anthony generally investments considered "Risky" like stocks and Real estate, tend to be risky short run  but less risky long run. Keep in mind once you retire you may stilll live another 30 years. That makes you a long term investor. 

      Regarding Real estate and risk, most people will disagree with m y next statement But   .   .   .  Real estate is the riskiest investment you can make.  The really important thing to understand about real estate is you get to control your risk. The more knowledge you have the less risky it is.  Follow people like @Jay Hinrichs, @Don Konipol, @Joe Villeneuve, @Chris Seveney and many other here you will learn about the risks and how to avoid them. 

      Well said, as usual, regarding the risk and risk control of REI.
  • Real Estate Consultant · Ann Arbor, MI · Member since 2022 · 465 posts · 255 votes
    1y

    Hi Janet from Raleigh, North Carolina-

    You are 54 and love your work at a non-profit and are ready to start investing in real estate.

    Your husband is risk-averse and looking to retire in 5 years.

    He's good with investing as long as your assets are protected from lawsuits and the investing is done thoughtfully and he is not involved in the property management.

    Recommend you look in an area that cashflows well at a reasonable price ($135,000 plus/minus) ideally starting with a duplex so you always have a rent check coming in and some work that could be done when the units become vacant to add value and increase rents. Then, plan to refinance in a year or two and use the equity to go buy the next one.

    You certainly want to have an excellent property manager to make your investment as passive as possible, investor insurance coverage from a knowledgable agent, and asset protection in place with an LLC and asset protection attorney.

    This is all doable in many markets in Michigan.

    To Your Success!

  • Todd AndersonPro Member
    Real Estate Agent · Cape Coral, FL · Member since 2023 · 392 posts · 175 votes
    1y

    @Janet Anthony,

    First off, It is never too late.  With every investor that I talk with, they all have a different goal and strategy to get there.  There is a way, for almost everyone who is interested, to invest in real estate.   I think some of the people that are the profitable are the ones who keep their jobs and just invest for wealth growth

    I love your Why.  That is the best reason to get started.  Because you have a solid Why.  I would recommend that you look at a strategy that many people overlook.  Look at New construction Build to Rent.  The investors that I work with find that they have less risk in a property that all the items are new.  With a turnkey Investment that can be loaded with incentives to make the investor more profitable.  You are also in a good market to find this type of investment.


    Best of luck getting your husband onboard, and please connect with more questions.  

  • Realtor · McAllen, TX · Member since 2025 · 141 posts · 58 votes
    1y

    Start looking and crunch some numbers. Make some friends with real estate agents, investors, wholesalers, property managers, tax pro, and a lawyer.  

  • Joe VilleneuvePro Member
    Plymouth, MI · Member since 2013 · 13k+ posts · 19k+ votes
    1y

    You are never too late...for anything in life.  If you say that about anything (unless someone marries your true love), you are admitting defeat before you even start to play.

    This reminds me of the age old question, "If you could change anything in your past, what would if be?".  My answer is always the same,..."nothing".  That's not because there may have been events that happened I wish hadn't happened, or things I could have done or did do, that might have changed the next event.  Great, things happened differently.  All that means is the next event changed.  That doesn't tell you about the new domino effect from that point forward.  All you know, is where you are now, and where you want to be down the road.  So, as @Ned Carey said as articulately above, Learn how to control your future through continuous education, and if there are opportunities you may have missed (not really missed, you just weren't there) in the past, just use your education to make them happen in the future.

    Learn from those past events (history), and repeat them for yourself.

  • Bill LeBusiness Member
    Rental Property Investor · Richmond, VA · Member since 2019 · 26 posts · 2 votes
    1y

    Hey Janet, we're based in Raleigh too, and I just wanted to say that you're definitely not alone. A lot of our clients are around your age and have recently bought their first rental or even converted their current home into one. There’s no such thing as being too late to start.

    Owning a rental is definitely active and comes with some risk, but it can be incredibly rewarding and a real path to building long-term wealth. Given your situation, a slightly more conservative approach makes a lot of sense—especially with retirement on the horizon and a more risk-averse partner.

    One thing to know about Raleigh is that we do see a strong pool of tenants, especially from the tech world. These renters are usually well-paid and take good care of the properties. The only thing I’d flag is that rent prices have leveled off here over the past couple of years after the big run-up during COVID. So just make sure your numbers work from day one and don’t rely too heavily on appreciation or future rent increases just yet. We are seeing rises again but I don't want to oversell it. 

    Keep digging into the research and leaning into your local REI group. It sounds like you're doing all the right things—just one step at a time.

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  • Nicholas L.Pro Member
    Flipper/Rehabber · Pittsburgh · Member since 2018 · 6k+ posts · 5k+ votes
    1y

    @Janet Anthony

    it's not too late, BUT one thing to be aware of is that your first 5-10 years are likely to be a period of INvesting, IE you spending money on your real estate.  there's sometimes an idea that you're going to purchase a property and start getting "cash flow" in month 1.  this is a myth.  it typically takes years to pay off just the transaction costs on the purchase.

    and as @Joe Villeneuve likes to remind us, if you shell out a huge down payment, that money is just sitting there until it's paid back somehow.  yes, it's part of your net worth but it can't be used to invest in other things or buy groceries without several other very expensive steps.

    just some things to think about.  only you can decide whether your financial situation permits you to do this and if being hands-on is something you're interested in.

  • New to Real Estate · Member since 2020 · 5 posts · 5 votes
    1y

    Wow! Thank you all for the wisdom and encouragement I needed to hear! I truly appreciate it. 

    @Todd Anderson you're right. I did overlook that strategy as one to consider and simply because my inexperienced ears hear "more out of pocket" but I'll definitely do the research. Thanks!

    My next step will be to find the investment that will work and then diving in...hopefully with my husband onboard by then.

  • John MorganPro Member
    Rental Property Investor · Grand Prairie, TX · Member since 2018 · 2k+ posts · 2k+ votes
    1y

    It sounds like you’re pretty familiar with how RE investing works. It’s definitely not rocket science. Anyone can do it. I started 10 years ago with a wife who absolutely hates that I bought all these rentals. But she’s good with the cashflow and was able to retire 3 years ago from her W2 from mailbox $. lol. I started when I was 44 years old. My profits now are 20k/month not including things breaking or vacancies. That’s definitely enough for me. My advice would be to buy something and tell your husband it’s your passion. That’s how I got my wife somewhat on board when I started. We had a lot of arguments at first so I agreed I wouldn’t use our savings to buy rentals. I got creative and used money from 401k and 0% interest for a year credit card loans. Then did some cash out refis to scale up for free. Good luck!

  • Investor · Milwaukee - Mequon, WI · Member since 2010 · 5k+ posts · 7k+ votes
    1y

    Not investing is also risky. 

    At least with REI you can control the risk. The cheaper the property, the higher the risk generally. Expensive properties have a lower risk profile.

    REI needs a 10 year runway.

    You don't make much money in the first years, but after a decade everything cash flows and equity becomes substantial and you start looking like a genius. The trick is to buy as much (quality) RE as quickly as possible - that is your growth phase and you should refinvest all income into more growth. And then hold it for a decade to let your portfolio mature and get profitable.

  • Paul Raymond WoodBusiness Member
    Realtor · Northwest Wisconsin · Member since 2024 · 9 posts · 1 vote
    1y

    As others have said- never too late to get in the game. The biggest regret will be living with the what could have been. My wife and I rented till our late thirties because I was too dogmatic with following the Dave Ramsey approach at the time and definitely live with regrets. This was during the time housing prices were skyrocketing on the west coast and interest rates were low- could have built some serious equity to be used for investing down the line. 

    Fast forward to now and we're in REI investing both local and out of state, but we could have been so much further along in the journey.

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  • New to Real Estate · Member since 2020 · 5 posts · 5 votes
    1y

    Thanks so much @Marcus Auerbach and @Paul Raymond Wood! Agree that not investing and not getting started is risky and maybe riskier. I hate the regret of inaction more than I do taking action. Appreciate you both and will check back in when I take my first leap soon.

    • Paul Raymond WoodBusiness Member
      Realtor · Northwest Wisconsin · Member since 2024 · 9 posts · 1 vote
      1y
      Quote from @Janet Anthony:

      Thanks so much @Marcus Auerbach and @Paul Raymond Wood! Agree that not investing and not getting started is risky and maybe riskier. I hate the regret of inaction more than I do taking action. Appreciate you both and will check back in when I take my first leap soon.


       You're very welcome! Feel free to add me as a connection and dm me if you want to brainstorm- I'm always excited to discuss strategy.

      REAL Broker LLC - 3 Rivers Team 512 Reviews
  • Real Estate Coach · Chicago, IL · Member since 2020 · 171 posts · 64 votes
    1y

    Hi Janet! Regardless of what anyone thinks, it's never too late to get in the game! Given your partners risk tolerance, have you ever thought of investing from a limited partner (LP) position? That way your family does not have to deal with the headaches of owning real estate while still capitalizing on some of the benefits real estate investing provides?

  • Ryan RomingerBusiness Member
    Real Estate Broker · Indianapolis, IN · Member since 2018 · 340 posts · 144 votes
    1y

    Really appreciate how thoughtfully you’re approaching all of this. It’s clear you’ve invested time into learning the landscape, and you’re not rushing into anything.

    Since your husband is more risk-averse and prefers not to take on debt or landlord responsibilities, it's smart to approach this with clear boundaries. One of the most important things—possibly more important than the strategy itself—is making sure you and your partner are aligned on the vision. Even if you’re the one taking the lead, being on the same page about long-term goals, risk tolerance, and asset protection will prevent conflict later on. Real estate works best when it’s a team decision, even if one partner is more hands-on.

    That said, starting small and staying in control is a great way to ease into it. You might consider a single-family rental in a stable, landlord-friendly market like Indianapolis. It allows you to apply everything you've learned with relatively low risk. If you're eligible for a VA loan, house hacking a small multi-unit could be another option—letting you live in one unit while renting out the others, learning property management in real time, and avoiding PMI with owner-occupant financing.

    If you're purchasing on your own, an LLC could help with asset protection, though you'll still likely be underwritten based on personal income for most loans unless you go fully commercial. You might also look at partnerships—where you bring the knowledge and oversight, and someone else brings capital. It's not a fast path, but it's how a lot of cautious investors get started without overextending themselves.

    And since your husband isn’t looking to be involved in management, professional property management will be key. A reliable PM can help protect your time, your investment, and your peace of mind—especially in an out-of-state market. Vet them thoroughly and treat them like an extension of your team.

    It’s clear you’re not doing this just for quick gains. You’re thinking long-term: about future flexibility, supporting your kids, and providing stable housing. That clarity is a huge asset. When you're ready for that first step, the goal doesn’t have to be big returns right away—it can simply be gaining experience and building a strong foundation.

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  • Realtor · St. Petersburg, FL · Member since 2024 · 55 posts · 40 votes
    1y

    Investor & Property Manager | St. Petersburg, FL

    Janet—first off, thank you for your service. And second—you are absolutely not too late to the game.

    In fact, your post tells me you’re more ready than a lot of people who do jump in: you've built knowledge, developed a clear "why," have solid credit, savings, VA loan access, and a thoughtful mindset about risk.

    I’ve worked with investors across all stages—and here’s how I’d frame your situation:

     You Have Key Advantages:

    • W-2 income: Makes financing easier.

    • VA entitlement: Zero-down financing on your first few deals, house hack or otherwise.

    • Great credit: Unlocks better terms.

    • Strong “why”: This is huge for staying the course.

    • You’re coachable: You’ve done the education work most never finish.

     You Can Invest Alone—Even If Your Spouse Is Risk-Averse:

    Lots of couples go through this. The key is to:

    1. Separate your investing vehicle (LLC, trust, etc.) from family assets.

    2. Use low-risk entry strategies like:

      • House hacking with a VA loan

      • Buying a small rental in your name through an LLC with liability protection

      • Partnering passively in a deal you’ve fully vetted

    You don’t need to go big or fast. One smart, cash-flowing deal changes everything.

     What You Could Do Next:

    • Run a live deal analysis with someone local or on BiggerPockets (happy to help with this).

    • Consider a duplex or triplex with your VA loan—live in one, rent the rest. Low risk, high control, and great learning experience.

    • Join a small joint venture where you’re not the active landlord—especially if your husband’s peace of mind is a factor.

    Bottom line: You’re not too late—you’re just early in your personal timeline.

    Start with one deal. Then use the momentum. You’ve already done the hard part—preparing your mindset and foundation.

    Feel free to reach out if you’d like a second set of eyes on a deal, or just want to talk through a safe entry point that fits your comfort zone.

    You're on the right path—keep going!

  • Member since 2025 · 5 posts · 3 votes
    1y

    It's never too late to get involved. Having access to VA Lending makes this even more feasible if you find the right location and asset. Additionally, there are typically some tax benefits that veterans can take advantage of in most states depending on status.

    As far as your spouses concerns go, my recommendation would be to forecast an ideal investment. It sounds like you have all of the info to determine a good investment from a bad one. Once you have determined the specifics of the investment you want to make, come up with a Pros and Cons list and do your best to mitigate the consequences of the Cons. Examples would be buying an asset with plenty of equity, whether that be sweat equity or just finding a good deal on an asset. That way if all of your assumptions go haywire, you can flip the asset to recover your costs. 

  • Peter MckernanBusiness Member
    Residential Real Estate Agent · Irvine, CA · Member since 2013 · 2k+ posts · 1k+ votes
    1y

    No! You should listen to Bill on Old Dawgs REI Network, he was in Orange County and recently moved out of state. The guy started investing at age 58! He got to 1,000 units from 2016 to 2024... He ran a podcast for years and focused on people over 50 then opened up the investment base for listeners to get to hear other stories, but great for you to listen to!

    https://podcasts.apple.com/us/podcast/old-dawgs-rei-network-...

    The McKernan Group4.957 Reviews
  • Real Estate Agent · Raleigh, NC · Member since 2019 · 308 posts · 288 votes
    1y

    Not too late - most people right now in 20s and 30s feel the SAME way because it's a tough market. If you want retirement income in 5 years, you do need to take risks however. Cash lowers your risk but is also the slowest way to grow. So you'll have to find a balance.

    One idea. Can you do a primary with low down and renovate it, and do that a few times, turn them into rentals when you move out?

    Would love to bounce ideas off of you, as I live and work in real estate here in Raleigh. I'll DM you :)

  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    1y

    You are thinking the right things and it's never too late. Think about it like This. Is your 10 year future self going to mind if you have 2-3 properties? Probably not. 

    That's unfortunate your husband is risk averse. I would educate him that not taking action in the face of inflation and higher costs is the riskier move in the long run. 

  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    1y

    @Janet Anthony You're in a great position to begin investing in real estate, even at 54, it's not too late at all. In fact, your combination of preparation, creditworthiness, VA loan eligibility, and long-term vision gives you more flexibility than many investors starting out.

    Here’s a clear way to think through your situation:

    Why You're Ready

    • VA Loan Eligibility: This gives you access to zero down financing for owner-occupied 1–4 unit properties. You could live in one unit and rent out the others—a great house hacking entry without needing your spouse to be actively involved.
    • Solid Financial Profile: Good credit and savings give you access to conventional, DSCR, or even seller-financed options. Plus, you may be able to tap into OPM (other people's money) from local REI partners.
    • Supportive—but cautious—spouse: Since your husband is risk-averse, you can structure the investments under an LLC to protect your shared personal assets and handle liability concerns separately.
    • Realistic Goals: You’re not chasing fast flips—you want long-term wealth and generational planning. That’s ideal for long-term buy-and-hold strategies that benefit from tax advantages and stable appreciation.

    Tax Considerations

    • Rental Income Benefits: Any property you rent for 14+ days per year qualifies for Schedule E reporting. You can deduct:
      • Mortgage interest
      • Property taxes
      • Insurance
      • Maintenance & repairs
      • Depreciation (27.5 years for residential rentals)
    • LLC Tax Treatment: Forming an LLC won't automatically reduce taxes by default, it's a pass-through entity. But it does support better recordkeeping, clearer liability separation, and partnership structuring if you bring in others later.
    • Real Estate Professional Status (REPS): If you materially participate and work 750+ hours/year in real estate, losses (including bonus depreciation) could offset W-2 income. If you don't qualify for REPS, STR (short-term rental) tax loophole rules might still allow this benefit if structured right.
    • Start-up and Education Costs: Once you begin investing, you can deduct expenses like courses, mileage, travel to view properties, and REIA membership, many people miss this opportunity.

    Next Steps

    • Look at VA loan house hacking as a low-risk first step. You're already entitled and it requires no cash out of pocket.
    • Start an LLC for your first rental if liability is a concern. You can keep the title in your name for loan qualification, then assign the beneficial interest or insure thoroughly.
    • Connect with a real estate CPA early, they can guide you on REPS strategy, bonus depreciation, and the best ways to track expenses from day one.
    • If you're interested, I can send you a downloadable checklist for starting your first LLC and a tax deduction guide for new investors.

    You’re not behind—you’re stepping in at the right time, with the right mindset. And because of your clear goals and thoughtful planning, you’re already ahead of most first-time investors.

    This post does not create a CPA-Client relationship. The information contained in this post is not to be relied upon. Readers should seek professional advice.

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