Five Years to Fortune (or at least less poverty)
July 13, 2020 2:20 PM   Subscribe

If you had five years to come up with a money-making scheme, how would you spend that time?

I am exactly half way through a 10-year stint at a public-service job that qualifies for the federal Public Service Loan Forgiveness (PSLF) program. Five years in. Five years to go. If all goes accordingly—and I realize that’s a big *if*, but let’s assume, for the sake of this question, that the government sticks to its promise—by 2025, my $100k+ of student loan debt will magically go bye-bye. I have no other debt. No kids, either. Just a single dude, biding his time in a one-bedroom apartment in a Midwestern city. I will be 40 years old.

While the work experience hasn’t been miserable, it’s a far cry from anything I ever wanted to do, and, quite frankly, trying to get by on $50k a year has been a slow, steady grind on my soul. I am so, so tired of being low income.

So, in an effort to not let the remaining years feel like a play clock I’m running out—or worse, a prison term—I’m trying to reframe the time as something valuable. And it’s true! For the first time in my life, I don’t have to make a desperate decision about career and finance. I have five years to make a plan. Five years to organize and prepare.

My goal: Come up with something—anything—to make more money. Public-sector work has shown me that I have horribly underestimated the level of income I need to live with adult dignity, and I want to make my next move with finances in the front of my mind.

So: If you had five years to come up with a money-making scheme, what would you do?

Suggestions can include retraining and traditional employment (coding bootcamp?), but I also want to solicit suggestions on investing, purchasing property, Air BnB-ing—anything that people savvier than me are doing to pad their bank accounts.

Only stipulations are that:
1. If it’s a job, it has to pay AT LEAST $75k (which is the combined value of my current salary and the value of my lone forgiveness)
2. If it’s retraining, it cannot be something I need to go into further debt over. I’ve learned my lesson the hard way.

Some things I’m actively looking into:
- Learning to code, possibly at a bootcamp (this seems to be the only well-paying sector of employment left these days)
- Buying a duplex, as an owner occupier, with the aim of having tenants pay the bulk of the mortgage
- Brainstorming a business that might capitalize on cannabis going recreational in my state, which appears highly likely in the next two years
- Simply spending five years learning everything I can about markets and investing, slowly plotting a portfolio strategy that I can fund gradually
- Purchasing cryptocurrencies or investing in blockchain tokens
- Taking a one-year travel job in my current field, where it’s possible to get $100k contracts to work in remote places like Alaska
- Sucking it up and moving in with Craigslist roommates for a year, which could cut my rent in half

What else should I be thinking about?
posted by sureshot to Work & Money (23 answers total) 15 users marked this as a favorite
I would definitely go for the travel jobs in your current field. At 40, you wouldn't want to throw away your life experience, and 100k contracts are great! Especially in remote places like alaska, where rent will be cheap. You'll meet new people! Exciting stuff! And, if your costs don't increase, you'd be debt free in two years!

I personally wouldn't consider anything else on your list. Crypto/investing are investment risks, not really capital generating. Roommates/duplex wouldn't allow you to find those contracts. Cannabis is run by big cannabis, because they are the only one jumping through all the regulations in recently-legal states.

Coding or re-education are options, but it's a bit late. If you have an in-demand education already, just roll with that, otherwise you will start from the literal bottom.
posted by bbqturtle at 2:45 PM on July 13, 2020 [5 favorites]

What do you do right now ("public sector" encompasses A LOT of things) and what is your educational background?
posted by btfreek at 3:07 PM on July 13, 2020 [1 favorite]

I would 100% say spend the year on the travel job, bank the money. Spend your spare time in the unfamiliar place eating all the foods and teaching yourself a skill. One hour a day of learning will give you a good jump start.

I most emphatically say boot camp is only a good idea if you already have had a taste of coding, know what you like and don’t like about it, and have talked to at least five people about what their coding job actually entails. Some folks are very very disappointed with their first tech role that they took because they needed the money and couldn’t turn down an offer.

Even better if you can build a network in the travel job place of tech people who might vouch for you for remote work.
posted by bilabial at 3:25 PM on July 13, 2020

Many of these options sound like things that may be very different in post-COVID US and I wouldn't bet on them.

However, does your current job translate to private sector in some way? Don't answer out loud to keep the details private, but just maybe poke around Indeed to see if the things you do show up in job descriptions. (If you want to memail me with more info about what you do, I can take a stab at suggestions - I work in a field that puts me in contact with all kinds of industries so I get to see a lot of interesting jobs.)

The kind of coding you learn at bootcamps is going to prepare you for jobs where you're going to face significant ageism, but if your current experience has aspects of reporting, analytics, data management you might find it interesting to go in a direction of the kind of query and programming languages used for business analytics and data science. That's the kind of thing I'm keeping in my back pocket myself, as a slight pivot from what I'm doing now.
posted by Lyn Never at 3:35 PM on July 13, 2020 [1 favorite]

- Learning to code, possibly at a bootcamp (this seems to be the only well-paying sector of employment left these days) You van learn basic coding online, lots of free options. find out if you hate it.
- Buying a duplex, as an owner occupier, with the aim of having tenants pay the bulk of the mortgage I did this for 20 years. Tenants are a huge pain, but I'd never have made it as a single parent with no child support otherwise. Not as passive as people think. But I built equity faster.
- Simply spending five years learning everything I can about markets and investing, slowly plotting a portfolio strategy that I can fund gradually Start now. The sooner you start, the sooner the market makes money for you.
- Purchasing cryptocurrencies or investing in blockchain tokens Very risky
- Taking a one-year travel job in my current field, where it’s possible to get $100k contracts to work in remote places like Alaska Yes, do this. Travel is almost always interesting, even if the placements ends up being horrible, a year is usually manageable.
- Sucking it up and moving in with Craigslist roommates for a year, which could cut my rent in half Get a nicer apt., share it and save only 1/3 but have nicer lifestyle.

Use this time to learn to be a manager or leader in your field.
Figure out why you hate your field, look for fields that don't have that. or ways to make peace with what you do.
Good ways to make money - get very good at sales. People who sell stuff well make a lot of money, and often have fun doing it.
Some small businesses pay well, contracting, electrician, owning a car wash or 3.

You have health insurance, good vacation and sick pay and make more than the median wage in the US, which is $31,099. You feel the socio-economics of not being wealthy or prestigious. Fake it. Don't tell people you make 50K. Learn to leverage that 50K to live well and have fun. Sadly, I've seldom made much money, but I'm frugal and have tons of common sense. I buy clothing, furniture, etc., at thrift shops and craigslist and I wait for good quality and great deals. I hardly ever pay retail. I pay no attention to what's trendy or impresses most people and have created my own style that pleases me.

People want to be around someone who has status, true. But also around someone who is interested, interesting, engaged. You sound like your life is on hold - that's no fun. Work on changing that.
posted by theora55 at 4:04 PM on July 13, 2020 [13 favorites]

What is your risk tolerance?

While it's possible you might make a lot of money investing in Bitcoin or by pursuing your own investment strategy it is much more likely than you will lose money.

I would strongly recommend against either of those options.
posted by nolnacs at 4:18 PM on July 13, 2020 [1 favorite]

Bootcamps unfortunately underdeliver and are oversubscribed. Their output is extremely variable with the main thing they provide being buzzwords on a resume.

They do this by having you complete already-structured projects where you touch (but do not deeply learn) a variety of technologies for which there are probably some jobs; they keywords on your resume get you through the first HR filter. They work best for people who are highly educated/skilled in an area who want to do programming/data science or something in that same area. They're not-great-to-terrible for people who want to start a new career.

That is not to say that "coding" isn't a possible career change, just that bootcamps provide questionable value in exchange for 10-15% of your first-year salary. If you are actually interested in a programming, everything you need is 100% free online to learn the skills, though getting a first job (even with bootcamp buzzwords) is going to be a challenge. If there is any way to use programming in your current position, that is an excellent way to get started as you won't have to invent problems to solve and will let you put these skills on your resume and show you can use them in the real world.

In terms of getting a pure programming job, the best thing you can do is to already be where there are jobs, e.g. SF or NYC. Second is apply to many, many, jobs. Third is to be able to answer lots of hackerrank (or similar) questions without breaking a sweat. On the other hand, you may be able to parlay your current position and familiarity with the field into a more-technical job in your field much more easily than effectively starting from zero and competing against new college grads.
posted by beerbajay at 4:39 PM on July 13, 2020 [3 favorites]

If you're comfortable, sharing what you do now could help with suggestions on how your skills could translate to a better-paying job. Get rich schemes, even legitimate ones, are not the same as making a good salary, living below your means, and saving/investing smartly.

The duplex idea is also promising, but do your research and know what you are getting into. It's not passive, but in my experience it's less work than airbnb, although also somewhat unpredictable and can require money when stuff breaks, or in between tenants. The best things to do are to buy a place you can afford without tenants, if at all possible; and get good tenants (and know how to do this ethically and without breaking the law, which is not always possible).

I also 1000% support the Alaska idea! Travel, live cheap, sock away lots of money. Making money often takes money so that's a good start in the next few years. If you can do that in the next year or so, it could go a long way towards a down payment for a duplex, or whatever else you decide to do.
posted by sillysally at 4:51 PM on July 13, 2020

The best way to make money is to earn it via a job (and/or cut your expenses) or luck (don't count on it). There aren't shortcuts until you have millions of dollars.

Because of this, you should pursue higher paying jobs in fields you have an interest and competence in already. That's not to say you shouldn't pursue a new field, but it should be one that you have an interest, competence and realistic chance of success in already. Do research on your field, find out how to make more money doing it. The travel job sounds promising, but also a big commitment. See if there are higher responsibility options in your field. Moving into a different industry is potentially a good idea, but be wary of opportunities that cost you something up front (and in particular boot camps).

You absolutely should not pursue investing in stocks or cryptocurrency or real estate. Stocks are simply a way for you to give money to better, faster, smarter traders with thousands of times your resources. Cryptocurrency is literally gambling. Real estate is risky, and a big commitment.
posted by so fucking future at 5:09 PM on July 13, 2020 [1 favorite]

To kind of thread the needle on a few answers, public service and nonprofit are desperate for data people, and their standards are low because they don't pay as well but it still could be a lot from your perspective. They will also like your demonstrated commitment to public service; people coming from corporate can find nonprofit culture and lower pay difficult and don't stay. Learn SQL and Access, become a nonprofit data person, there are a whole raft of people making their way in service oriented jobs who know more about data than the next person. Not enough to get a real tech job but enough to be really valuable in meaningful settings. This is the clearest path to 75k in your position.

Source: i'm a web developer who has worked in house and consulting with nonprofits but has fled back to corporate.
posted by Kwine at 5:17 PM on July 13, 2020 [12 favorites]

Until you can get $$$, take a good look at how you can cut your expenses without pain or misery. If somebody offered me $50K a year -- even $50K Canadian! -- I'd think I'd hit the fucking jackpot, and I still have a pretty nice life.
posted by kate4914 at 7:05 PM on July 13, 2020 [4 favorites]

Learn to code! It’s really not too late. I started considering coding at 31 & played around with it, learned enough to volunteer & also write a demonstration app, had my first related job by 33. I’m now almost 45. I stumbled into a niche area in my career and have been able to “brand” myself around that niche for nearly 10 years. Prospective employers in this area are forgiving of any tech skills gaps, because I understand their challenges & business vocabulary.

At 44-1/2, I’m presently learning a new programming language and some new technology that solves problems in my field, but it doesn’t feel like I’m starting from scratch. The pay is not glamorous, but much higher than you are earning. I could have pursued other opportunities.

I’ll recommend two resources. One is Josh Kemp’s book, No Degree? No Problem.
Read Section One and Section Two. And Section Four. Follow his advice on networking at Meetups. But don’t learn Ruby on Rails. And don’t have a blog. Instead focus on an area of expertise to develop based on your local market. Maybe data visualization or big data management, or JavaScript. But otherwise, implement his advice. The second is Software Developer’s Career Guide by John Sonmez. Read the sections that apply to you.
posted by ElisaOS at 8:04 PM on July 13, 2020 [8 favorites]

I deleted a long, detailed post before this one because it bummed me out, but here's the gist:

1. Assume that really bad recession/depression is coming that will last 5 years or more.
2. Your goal should be making friends with rich people and getting money from them - not institutions/markets/businesses.
3. Start a non-profit in your field of expertise. Use that to meet and get money from rich people.

Bonus: Maybe help not rich people if you can along the way.
posted by Anoplura at 8:16 PM on July 13, 2020

Simply spending five years learning everything I can about markets and investing, slowly plotting a portfolio strategy that I can fund gradually

Invest in the S&P 500.. (Not just my advice, but of perhaps the most successful investor in history.) Now you can use your 5 years more productively. You may want to spend that time studying to be a financial professional - CPA, advisor, etc. - but the key there is that other people are paying you, you aren't trying to beat the market with your own money.
posted by Mr.Know-it-some at 8:52 PM on July 13, 2020 [2 favorites]

A previous commenter wrote:
I would definitely go for the travel jobs in your current field. At 40, you wouldn't want to throw away your life experience, and 100k contracts are great! Especially in remote places like alaska, where rent will be cheap.
Unless the "midwestern city" the poster lives in is Chicago or subsidized housing is part of the contract, it is not all that likely that rents in Alaska will be cheap by their standards. And in remote communities housing stock may be very limited and/or comparatively primitive. Furthermore, fuel, transportation, and food costs can eat up a lot of that salary pretty quickly.

That's the bad part. The good part is that for a certain type of person Alaska offers amazing opportunities for exploration and adventure. But know what you're getting into first, especially if accepting a contract position in a small remote community. Quality of life can vary widely.

Oh, and.. I very much fear that Alaska is headed for some really grim economic times. You would be wise to at least have a solid Plan B. A lot can happen in five years.
posted by Nerd of the North at 11:40 PM on July 13, 2020 [2 favorites]

Just start saving and investing for no reason. No need for a plan. Just aim to match your debt with new savings that allow you to plan your exit when you have hit your own criteria.
posted by parmanparman at 1:00 AM on July 14, 2020

Right now today? Tech nomading is over. At least for a long time. If you can do programming, learn it. If that's not your jam, get a CPA. Lobby for fully remote work so you can go where you want later.

Yes to investing. Dont use Robinhood or whatever bs apps exist to turn you into a day trader. Buy some solid EFTs and be patient.

Get some roommates. I'm in my early 40s and have 2 of them. They are lovely, and keep my rent to an actual reasonable level. Ask yourself if it's truly worth 2/3 of your annual rent payments to live alone. That money can go toward so much better ends.
posted by ananci at 2:02 AM on July 14, 2020 [1 favorite]

Simply spending five years learning everything I can about markets and investing, slowly plotting a portfolio strategy that I can fund gradually

No, don't waste your time learning about investing (unless you want to take the tests and become a financial advisor). You don't make enough money to make a difference. Open an IRA to start with. You individually can invest $500 a month. I recommend Vanguard Total Market Fund, but there are other companies (like Fidelity for example) that offer something similar. You don't need to 'learn' about investing, you just need to do it for a long time. Do not daytrade. Invest and leave it. For many years if not decades.

Do not do anything with bitcoin.

I recommend roommates personally because those $100k contracts are actually harder (and worse) to come by than they sound.
posted by The_Vegetables at 8:34 AM on July 14, 2020 [2 favorites]

Open an IRA to start with.
A regular IRA will also put a bit of tax money back in your pocket every year.
posted by The_Vegetables at 8:37 AM on July 14, 2020 [1 favorite]

Oh the other thing I was going to say:
- despite COVID, you can still network at Meetups. Many are meeting virtually and online.

- you already have a degree or credential. don't get another one. just learn to code, put up a good demonstration of your work on Github and the web, and network around that.

- 5 years of public service sector experience is nothing to sneeze at. is there an area of programming or data analysis that solves problems in your field? if you are at an office, go talk to the IT or database people. what kinds of problems are they solving? if you can solve them, that could be a career. Being the person in an organization who can code, is often better than being part of an IT team in a software development company.

- Public sector places that need apps/data management/data analysis: public health, government benefits offices, public transportation, parking, public school system, jails and prisons, pension and retirement benefits, public utilities, business development, city planning. . .

- Start with solving problems in your current position. My first true 'paid' experience in IT was as a secretary. I created an MS Access database to solve a recurring problem. And I wrote a script to resolve a monthly billing task that resembled the knapsack problem.

- Forget the worries about ageism. Yes, those hot SF and NYC startups are looking for 21-year-old recent grads. Those grads are good, fast, cheap, and they know the newest technologies. You're not going to compete with them -- even they won't compete with them in 9 years. Don't go to work at a hip startup. Look elsewhere. All you need to do is solve problems for an organization, and all organizations need someone to do this stuff.

- Don't knock making money with Microsoft products. There are people making a good living just by being good at analyzing/visualizing data in Excel. Dave on Data has some great trainings and content around this. People in the tech world make fun of MS products, but hey -- you can laugh all the way to the bank.
posted by ElisaOS at 10:27 AM on July 14, 2020 [2 favorites]

You absolutely should not pursue investing in stocks

I couldn't disagree with this more. It won't make you rich in five years, but in twenty years it might, and as far as I know, it's the only way to retire at any age w/ a decent nest egg. I agree with others upthread that learning about investing isn't necessary, just go w/ a very low-fee total market index fund (and, if you want to go wild, a couple of other index funds) and let 'er sit.
posted by nosila at 11:14 AM on July 14, 2020 [4 favorites]

Making a fast killing in the market: highly unlikely. Possible if you are the trader for others and make excellent commissions and bonuses. These jobs are not trivial to obtain.
Making money investing in stocks: Save as much as possible, invest, repeat. Over time, this is an excellent way to make money; this is how the wealthy get wealthier. Much of it is low-tax or tax deferred.
posted by theora55 at 1:41 PM on July 14, 2020 [1 favorite]

I would learn the ins and outs of real estate investing. House hacking (living in one unit of a small multi-family home) is a good idea if you learn how to do it properly. You need a strategy, you need to learn how to run the numbers, and you need to be able to spot a good deal from a bad one (and know what that means to you)--but it is definitely doable. An FHA loan may be helpful if you don't have a lot for a down payment. Living in the Midwest is helpful in that properties are less expensive than on the coasts. The key is to really, really learn it.

Building Wealth One House At A Time is a good book to start with.'s Education tab has great info but might feel overwhelming if you're new to real estate investing. If you want to ease into it, I'd look through their podcasts and listen to a few that jump out at you on high speed. This one in particular was great--the interviewee talks about quantifying risk and building risk mitigation into her deal analysis.
posted by saltypup at 10:59 PM on July 14, 2020 [2 favorites]

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