Unretirement: Best Ways for Boomers to start making money online, and why they should

For those of us who are Boomers, or late Generation-Xers, and who have good jobs with good companies, here’s something to keep in mind:

The older we become, the more likely that it will be us, rather than our younger colleagues, who will be downsized when the cost-trimming starts.

And, of course, getting a new job will be incrementally more difficult for the same reason.

This was exactly what was in my mind in 2009, when I started my own business.

Today I am ‘unretired’: I run my own small business that keeps me sharp, active and involved. And I plan to continue doing this for as long as I can.

Unless we are privately wealthy, it makes enormous sense to find a side-hustle, from which we can start building an income, while we still have the security of a regular salary.

If you do a search online for ways to make money in retirement, you will find a load of results that say things like ’15 ways to make money online’, or ’35 ways to make money online’, or even ’99 ways to make money online’.

The problem is, many of those articles duplicate the methods they suggest, many of the methods are not sustainable and lots would not appeal to me, a boomer, in the slightest.

In this post I’ve researched, set out and linked to, the most sensible ways in which any of us late Gen-Xers, or Boomers, can start a good, sustainable side-hustle. One that we could turn into a full-time hustle if we wanted.

Introduction to ways for Boomers to unretire

There are lots of ways to make money on-line, but they mostly fall into two broad categories:

  • Selling your time
  • Selling stuff

If you’ve been researching ways to earn extra money, you’ll have seen lots of schemes promoted by people telling you that they’ll make money for you while you sleep or lie on the beach.

Steer well clear of those!

You’ll end up spending a lot of money for out of date processes.

There are also a lot of out-and-out scams flying around, so keep your wits about you if you go looking online for ways to make money.

The methods and resources I’ve covered below are sensible, sustainable ways for late Gen-Xers and Boomers to build up an independent income.

Why would you want to start a side-hustle?

Here are some reasons, in no particular order:

  • You don’t want to retire
  • You don’t have enough savings for retirement
  • You’re passionate about <whatever it is> and you’ve always wanted to promote it
  • You just want a bit of extra cash without too much time-commitment
  • You want something you can work into your schedule while caring for an ageing parent
  • You want to be able to travel and make money at the same time
  • You can’t stand your daily commute
  • You want to be in control

So let’s look at some ways to make money on the side. As I said earlier, broadly there are two ways:

1. Selling your time

Some of these ways to make extra cash don’t require a big commitment of your time and many don’t require any qualifications.

But they also don’t make a lot of money.

There are others that do require either a steady commitment or specific experience or skills. Virtual assistants (a steady commitment) and resume writing (HR/hiring experience) come to mind.

None-the-less, all the options I’ve covered below involve selling your time and are not, therefore, easily scalable.

So let’s take a look:

Data entry jobs

These are generally pretty straight-forward but repetitive and boring. The benefit is that as long as you can type, have a computer and an Internet connection you can do the job. Those are about the only qualifications you need.

The downside is that there’s not much money to be made with these jobs.

You can do a search online for data entry jobs but you need to be careful to avoid scams.

If data entry work sounds like it might suit, you would be better going to a reputable data entry agency or exchange like Axion Data.

The Work at Home Wife website has other data entry sites that would be worth reviewing.

Take surveys

This involves taking product surveys or participating in focus groups, in return for which you will be rewarded with cash or vouchers that you can turn in to cash.

More interesting than data entry jobs, this is still little more than a side-gig and won’t make you rich.

Companies like Survey Junkie enable you to register and specify your interests. They then allocate you surveys submitted by corporates on products in which you’re interested.

If you’re curious or interested in particular industries this can be quite an informative gig as you will get to know different products.

Other survey job boards include Branded Surveys, Inbox Dollars, and Get Paid Surveys.

Download the Nielsen App

This one actually requires none of your time – but it’s not one that I would consider. I’ve explained why below.

Believe it or not, if you install the Neilsen app on all your devices you can earn money for doing nothing other than browsing the Internet as normal.

Nielsen is a market research company and their app tracks your online behaviour, which is then used by Nielsen as part of their market research services.

This is not something I would recommend as you need to provide a fair amount of information about you and your household when you register, and you’re then tracked online 24/7.

If you’re concerned about privacy online this would be one to avoid!

But, if you’re not too worried about that, the details are here.

Register with crowdsourcing exchanges

These jobs require a bit more commitment, and they require that you have a particular skill (graphic design, programming, translations, market research, etc).

Companies use these exchanges to find short term talent for specific projects. Freelancers use them to make themselves available for projects.

You register with an exchange, specify your skills, qualifications and experience, and they notify you when a project for which you’re suited comes up.

You can definitely earn more money this way – some people earn their living from work they get through an exchange.

But you still have the flexibility of declining opportunities although, with some exchanges, if you do that too often you will stop receiving invitations to pitch.

You can pick up projects involving almost any type of work through one of these exchanges, from resume writing, through surveys, market research to programming and more.

Here are some crowdsourcing resources:


OneSpace focuses generally on non-technical areas, such as market research, marketing, editing, transcription, translation and more.

Here’s the OneSpace website, and here’s their application form (which indicates the type of projects they handle).


Fiverr started out as a freelance services exchange where everything cost US$5 – for example if you wanted someone to create a logo.

Today the price varies according to the project, but it still sells itself on offering services, provided by registered freelancers, for a fixed price.

Fiverr focuses on a wide range of disciplines, many of which overlap with OneSpace. Two that don’t, though, are programming and tech, and video and animation.

Here’s the Fiverr website, and here’s where you register as a freelancer.


Companies post projects on Upwork, and the Upwork system compares the project requirements with your skills and notifies you when there’s a match.

In addition to providing companies with specialists to handle specific projects, Upwork also caters for companies looking to hire permanent staff.

Upwork is the most extensive exchange that I found and would be worth a closer look.

Here’s the Upwork website.

Virtual Assistant (VA) type work

Offering yourself as a VA enables you to provide administrative assistant services to as many customers as you can handle.

Clearly this requires more time commitment, although the amount would depend on how many clients you took on.

But, even with just one client, there is a greater commitment on your part here.

Your customers will be relying on you to handle their administrative work, and these can become permanent, albeit part-time, engagements.

You can find VA jobs at UpWork and Indeed.

Resume writing, copy editing and similar work

Resume writing is obviously reasonably skilled, and you would have an advantage if you’ve worked in HR or a discipline focused on hiring or recruitment.

Again, UpWork is good for resume writing gigs.

If you’re not sure about Upwork, though, you can always look at this page on FrugalForLess, where they link to 8 sites that look for resume writers.

2. Selling stuff

Selling stuff is the other main way to make money online.

The primary difference between selling your time and selling stuff is that selling stuff is more easily scalable. It’s a products-based business rather than a client-based business.

This may give you more flexibility in where you choose to live, or in case you want to travel.

There are, broadly, two ways to sell stuff online: with a website and without.

Selling stuff online – no website

If you enjoy buying and selling stuff, or selling your own products, you can set up a nice business on Amazon, eBay, Facebook or Instagram.

The advantage of using these platforms is that you don’t need a website or any particular technical skills.

The disadvantage is the that competition is fierce and, with Amazon and eBay, when you take into account the fees they take, your margins are pretty thin.

None-the-less, this is an easy way to get into business selling stuff online.

One skill you will need to develop, though, is the ability to market online and, in particular, to market on Amazon or eBay.

These platforms each have specific characteristics and you will do better if you study and understand those.

One thing to keep in mind, though: on all of the platforms I’ve covered below you’re building your business on someone else’s ‘property’. You’re renting web space.

On all of them you have to abide by their terms and conditions.

These can, and often do, change at any time and if you fall out of compliance they will take down your products, or your page, overnight. This will put you out of business – at least temporarily.

If the business you’re building is for the long term, you should aim to eventually migrate it to your own, fully-owned, website. That’s where you will have complete control.

That said, let’s look at each:


Amazon needs little introduction. However, as customer-friendly as it appears on the surface, Amazon is pretty ruthless with its sellers.

Initially, while you’re still developing your business, it will be difficult to get support via anything other than standard FAQs – which can be frustrating!

On the other hand, it almost doesn’t matter what you want to sell – Amazon probably caters for it.

Here’s the page to sign up as a seller on Amazon.


eBay, also, needs little introduction.

It started out originally as a place for people to sell their own second hand stuff, and it still caters for those guys.

But there are also so-called ‘powersellers’ – people who buy and sell stuff.

It operates in much the same way as Amazon, but with the added option of selling either at a fixed price or putting your article up for auction.

While not as big as Amazon, eBay still claims 182 million buyers – a pretty reasonable market size.

Here’s the link to sign up as a seller on eBay and here’s a useful link with some training on how to sell on eBay

Facebook and Instagram

Selling stuff on Facebook and Instagram is edging across the spectrum towards having your own website. You don’t, of course, you have a page (Facebook) or an account (Instagram).

But in both cases, you are doing more than simply uploading products and selling them, as with Amazon and eBay.

On both FB and Instagram, you can develop a brand and you have the opportunity to establish a closer relationship with your followers and customers – which is more difficult on Amazon and eBay.

Both Facebook and Instagram are constantly making it easier to sell products on their platforms, a trend that will continue.

If you have large followings on either platform, and you want to sell stuff that’s relevant to those followers, you’re in a great position to get going.

On both platforms you will need to set up a page (FB) or a business account (Instagram). Once you have these, you can upload your logo and establish your business’ credentials, opening times, contact details, etc.

Selling stuff on Facebook or Instagram is well established and it’s a great way to get started if this is your first go at selling online.

Selling stuff online – with a website

I said earlier that the only place you have complete control of your business is when you have your own website.

But there is a distinction here too.

You can set up a website for free on services like Wix, Weebly or Squarespace but you are still renting.

Those services own the platform on which your website is set up and, again, you have to abide by their terms and conditions.

Once again, it’s quite possible for any of these platforms to change their terms and conditions and, if you fall out of compliance, your website will be taken down overnight.

The only time you have complete control over your website, and all your content, is when you go through the process of registering your own domain, signing up with an independent hosting provider and building your own website.

This is a service that I provide through my WordPress agency – please get in touch if you want to know a bit more about what’s involved (absolutely no obligation!).

So with that understanding, let’s look at ways of selling stuff through your own website.

Selling your own products

If you have your own product or products to sell, you’re in great shape.

You just need to set up your website with an eCommerce function, add your products, hook up with a payment gateway – I recommend PayPal if this is your first time – and you’re good to go.

Of course, you will need to establish your business – tax and legal, inventory, delivery, invoicing and collection and so on. This post covers how to start your own business.

To be successful you will need to get to grips with marketing online.

This is a big subject – there are lots of books written about it, and you will never stop learning because it evolves all the time.

But, if this is your first time, you should take a look at this Beginners Guide to Marketing Online.

It introduces the various channels and ways that you can market online and will give you a good overview of what’s involved.

But, again, this is a subject that’s continually evolving and you’ll need to evolve with it. It’s a subject for continual learning!

Selling someone else’s product – dropshipping

Dropshipping is a good way to set up an online shop if you don’t have your own products to sell.

With dropshipping you find a manufacturer or supplier of products that interest you or sell well. You buy them at a wholesale price, add your mark-up and sell them at a retail price.

You have your own website on which you set up your online shop. The customers buy from you, so you own the customer, but you don’t store or ship the products.

That’s done by the dropshipping supplier.

This is the online version of setting up a bricks and mortar store, where you’re buying stuff at wholesale prices and selling at retail prices.

The nice bit is that you don’t have to worry about stock, inventory or deliveries – that’s done by the supplier.

But that’s also a downside because it’s something over which you don’t have direct control.

If your dropshipping partner is efficient and reliable there will be no hassles. But if they are not, your customer will complain to you about late or damaged deliveries and you will have to sort out the problem.

This becomes difficult and stressful if you have an inefficient or unreliable supplier.

With dropshipping the key to a successful business is finding reliable partners, and one of the best places to do that is with SaleHoo (that is an affiliate link).

If you’re interested in dropshipping SaleHoo is an excellent resource.

As with selling your own products, you will need to learn about marketing online.

Selling someone else’s product – affiliate marketing

A different way of setting up an online business when you don’t have a product of your own to sell is affiliate marketing.

This differs from dropshipping in that you don’t sell any products on your website. Instead, you review and recommend products and send your site visitors to the product owner’s website.

If the people you send over end up buying the product you get a commission.

Affiliate marketing is almost entirely hands-off. The product owner does the selling, owns the customer, handles inventory, shipping and customer support.

You simply get a commission when people you refer to the product owner’s website buy the product.

Affiliate marketing is successful when you can get lots of visitors to your website and write good reviews of the products you’re promoting.

It’s also one of the cheapest ways of setting up a sustainable online business.

Once again, you will need to understand how to market online!

For a look at the differences between these two business models, and an overview of each, take a look at this comparison between affiliate marketing and dropshipping that I wrote recently.

I’ve been doing affiliate marketing since 2006, so please add a question to the comments area below if you want to know more about it.

You can also read more detail on these posts: How to get started with affiliate marketing and a review of the best affiliate marketing training for beginners.

Fun Flashback

Something from my youth to bring a smile to your lips:

Wrapping it up

OK, so there’s quite a bit of information there. If you have questions do please post them in the comments area below as that, and my response, will be helpful to others.

The key point I want to make if you’re dipping into this for the first time is to watch out for scams – there are plenty of them.

Always go for quality and avoid the hypey headlines promising secret systems.

Any make-money-online website that has pictures of young, smiling people (usually males) leaning on expensive boats or fast cars should be avoided..!

If you have any questions or would like to suggest other good resources that you have found, please leave a comment!


Martin Malden

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