100 ways to escape the 9-to-5 and make a living on your own terms. Part 1.

Olga Pope
13 min readSep 14, 2021

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Based on Courier Magazine’s 2021 guide.

llustration by Julia Gnedina from Ouch!

Newsflash: earlier this year Courier magazine published a bigass issue covering 100 of the latest, greatest ways to make a living in a less 9-to-5, more self-high-five way. It’s a real must-read to anyone who’s wondering if there’s more to life than a few decades of serving as office plankton, followed by retirement. From simple side hustles to mini-empires, those Courier people have covered some seriously cool active and passive income ideas. And do you know what else is cool? This. This thing you’re reading. Because, to save you hours of time as well as any number of potential papercuts, I’ve distilled and summarised the hell out of the whole thing.

The result is a summary of the most important global startup trends, business ideas, lessons, tips and hacks from hundreds of entrepreneurs who have found joy and purpose (as well as copious amounts of cash) outside of standard office jobs. Feel free to use it to plan out your great escape from Corporate Land, come up with the next Monzo or Borrow My Doggy, or just brainstorm a few ways to sponsor your sneaker addiction.

There’s so much good stuff in there, even my summary is a longass one — so I’m breaking it into quarters. Each idea comes with a takeaway — and the best thing is, those takeaways are pretty universal, so even if running a dog grooming salon isn’t for you, it’s worth checking out the insight or tip that comes with it, instead of throwing the baby (puppy?) out with the bathwater.

If you don’t want to miss the other 3 parts, you can subscribe to my newsletter here: weneedtotalkaboutyou.com/newsletter

Idea 1: Campervan rentals.

Example: Quirky Campers was born when a couple went to work abroad and had to leave their own beloved customised campervan behind.

Takeway: If your service is about experiences, make sure those experiences are pretty damn special. With Quirky Campers, every campervan has a personality and a one-off unique design. Basically: if it’s not good enough for you, it’s not good enough for your customers.

Idea 2: A cassette tape store.

Example: Taro Tsunoda’s cassette tape store called Waltz was born out of his own 10K+ cassette tape collection and the realisation that this vintage medium was making a comeback. He saw that tapes changed the way he listened to music: no skipping, no shuffling, just the album in the correct order, and obviously no Spotify ads — it was as close as it gets to the way the artists actually want people to hear their work.

Takeaway: In an era of digital everything, a physical format can have unique appeal as well as nostalgia value. So don’t burn or bury your old stuff just yet: ‘old’ and ‘vintage’ aren’t so far apart.

Idea 3: A kickass gardening or land-based project.

Example: The Ron Finley Project, a regenerative gardening movement. It’s not just about harvesting your own beets, mind you. The founder Ron has turned it into an absolute beast of a project, including a viral TED talk. ‘I want everyone to give a fuck about something other than themselves,’ says Ron, who is an absolute badass by the way.

Takeaway: As a recovering adland dweller, I love Ron’s view on working with brands: ‘We have to deal with the devil to change shit. As long as you don’t compromise what you’re doing.’ In other words: you can work with big corporations, but let them know who you are and what you stand for.

Idea 4: An independent publication.

Example: ìrìn Journal is an independent travel and culture magazine focusing on Africa. Its founder, Lagosian Ayomide ‘Mimi’ Aborowa says it was designed to plug a gap: ‘There’s always an image that draws travelers to a place — but we haven’t developed those stories for Africa yet.’

Takeaway: Analog print isn’t dead (Courier itself is a physical magazine, too — and a pretty chunky one at that). The medium is as old or new as the things you plan to say in it.

Idea 5: An independent photography agency.

Example: Alex Strohl, founder of photo agency Stay & Wander and mountain retreat Nooq.

Takeaways (a hat-trick on this one!):
Alex says you should never have lunch alone: ‘You can be the best creative in the world, but if you don’t know the right people, you’re going to struggle.’

Every new project Alex jumps into, it happens organically: he doesn’t gamble on a half-baked idea or put down money he didn’t have.

Alex says passion isn’t enough, because you won’t feel passionate every single day. Dedication and motivation is what keeps you going.

Idea 6: Spices without the middleman.

Examples: Diaspora Co, Warndu, Burlap and Barrel, Desert Provisions, Zoe’s Ghana Kitchen

By working directly with the growers, these startups can focus on the quality of the farming, the flavour of the products, and the practices of the businesses they buy from. That means farmers and workers not only take home a higher profit, they are also compensated for their skill and integrity.

Takeaway: This type of work isn’t for the impatient, because there’s a lot of legwork involved: it’s not always easy to reach the farms and businesses necessary to create a direct supply chain.

Idea 7: Indie delivery platforms

Example: Early Bird Courier.

Employees of global delivery companies, are recognising an opportunity to do work they enjoy but in a way that’s aligned with their own values — and on their own terms. That’s how Early Bird Courier was born, too — plus the co-founders felt that they actually LOVED cycling, unlike many other bike-riding delivery people working for big companies.

Takeaway: Even with an in-demand service like this, you still need a niche or some unique angle: for example, Early Bird Courier specialises in delicate deliveries like cake and event deliveries, as well as chefs operating out of dark kitchens and selling through social media.

Idea 8: Dog grooming.

Example: Harley Doggie Day Spa is just one of many dog grooming businesses that have sprung up in the last few years to meet the demand. Dog ownership numbers have grown massively during the pandemic, and people are now spending more on pet care than ever before. Many of the new pet owners are now returning to office work and travel, which creates a huge demand for dog walkers and sitters, especially those who offer training. Pet insurance is also fast moving from luxuries to essentials.

Takeaway: Personalisation, including science-based customisation of product or service, is a great approach and a growing trend in several booming sectors, including luxury petcare.

Idea 9: A rug company.

Examples: Ruggable, Cold Picnic, Kahoko, Okej Studio. The rug industry is due a makeover, and these are a few of the people already making it happen. One example of rug innovation is Ruggable’s patented two-piece washable rugs that are perfect for people with kids and/or pets, with a top layer that fits in a standard washing machine. Other startups, like Okej Studio, are blurring the lines between home décor and collectible pieces of art. They are breaking the rules on what a rug is supposed to look like, or how it should be made: they were a catalyst of the trend for using tufting guns, which has been exploding on TikTok.

Takeaway: Keeping your head is overrated: sometimes there’s gold to be found right beneath your feet. In other words: look around you, because there’s still plenty of stuff that could work better, or just look better.

Idea 10: Renting out your assets.

Example: Fat Llama, UK is a platform offering anyone the chance to make a passive income by renting out what they’ve got: from drills to designer bags.

Takeaway: Peer-to-peer lending is a growing trend of the sharing economy.

Idea 11: Internet-based beverage company.

Example: Cold-brew coffee brand Sleepy Owl, India. Granted, the coffee market is a saturated one in the Western world. But no one was doing it in India at the time Sleepy Owl was conceived — so the founders saw an opportunity to create and occupy a whole new retail category. Once it took off, they saw that people were taking pics of their cold brew coffee and posting it online — so they came up with branded enamel mugs and tumblers. It took a while for retailers to believe in the value of the product; it was only after selling online for a few years that retailers finally saw the brand’s potential. But even though Sleepy Owl is now stocked by a number of retailers in two major Indian cities, they see massive value in their online presence.

Takeaway: As much as every founder wants to see their product gracing the shelves of a physical store, selling online has huge benefits, and might be better for your brand — because it lets you speak directly to your customer and put a face to the brand name.

Idea 12: Basically anything to do with biodegradable packaging.

Examples: Coolhaus, Silent Pool Distillers, Common Heir. The biodegradable packaging market is set to be worth $127 billion by 2025. From ice cream (Coolhaus) to gin (Silent Pool Distillers) to vitamin serums (Common Heir), there are people rewriting the rules and reimagining what products can look like in order to be environmentally friendly.

Takeaway: Go to a supermarket. Find a product category that’s not packaged in a biodegradable way (which is, basically, everything except eggs and loose onions). Package it better. Get ready for fame and fortune.

Idea 13: Selling vintage goods on Instagram.

Examples: @maudvaughaninteriors, @maro_athome, @scenebychloe, @finnavintage, @scout__goods

Takeaway: Sometimes Instagram is the only medium you need. This type of product, usually picked up at obscure car boot sales and in small-town charity shops, lends itself to Instagram naturally and perfectly. Of course, you do need to have your own visual style and be good at presenting what you’re selling. You should use the medium’s built-in features to your advantage: for example, Stories can help you tease your audience and build anticipation before you post the items. Telling people what time each piece will ‘drop’ also helps a lot — this way many items sell ultra-fast.

Idea 14: A home restaurant.

Example: Han Oak is a family-run modern Korean restaurant that’s hosted in an actual family home.

Takeaway: Personality is everything. An authentic interior, including items collected by the host, will be a major part of the attraction — and in the case of Han Oak, the family’s two children are an inseparable part of the experience, as well.

Idea 15: Anything to do with barbering.

Example: Wecasa, ShearShare, Squire, TRIM-IT, Cuts & Creps, 1981

Remember the DIY haircuts of the pandemic? …Exactly. Some things are best left to the professionals. The male hairdressing sector is growing fast — and barbering is here for the long haul. Beyond becoming a craftsperson yourself, there are other ways to build a business within this booming area: from training other barbers off- and online or creating specialist products, to building digital platforms catering to salons, freelance mobile barbers and their customers. Bricks-and-mortar shops can also innovate, for example, by being sustainable like Cornwall-based zero-waste barbershop called 1981, or by offering services beyond follicular-related ones: Bristol’s Cuts & Creps offers a sneaker-cleaning service as well as buying and selling sought-after sneakers.

Takeaway: It’s great to have an in-demand skill, but you won’t get far just by swapping your time for money. Think bigger. Consider the entire ecosystem that this demand creates: from training to logistics, waste management, products and supplies, distribution, bookings, online and offline offerings connected to that sector. There’s gold in there.

Idea 16: Premium preserves.

Example: Fishwife, a premium tinned fish brand. Like so many startups, Fishwife was born out of the founders’ own needs. During the lockdown friends and business partners Becca Millstein and Caroline Goldfarb discovered a lack of convenient, sustainable and healthy food options — so they filled that gap themselves while adding a brilliantly artistic angle to a product category that’s not famous for its aesthetics.

Takeaways:
Building a supply chain is really complicated and takes a while if you don’t have much experience in the industry — but don’t forget that your new partners will be experts in the field who will take care of a lot of the complexities you might not even be aware of at the start.

Branding can be a make-or-break component for any company. To stand out, you have to go for a distinct and unique look and feel, as well as tone of voice. If you can pick an independent artist who can become your brand’s voice, do it — and pay them well.

Idea 17: Wine innovations.

Examples: Glow Glow Wines, Renegade Urban Winery, A Glass Of, Margins Wine, Cépage.

As well-established as it is, the wine industry is filled with areas begging for improvement and innovation. From sustainable portion-based packaging (A Glass Of gives you the chance to try one glass of wine from small-batch winemakers without splashing out on a whole bottle; plus all the wines cost exactly the same) to giving a chance to under-represented areas rather than the A-list places like Napa Valley (Margins Wine), or simplifying the process of choosing a wine for non-experts: like wine based on your mood (Cépage).

Takeaway: Pick a category you’re interested in, then interrogate every single aspect of how the industry operates and how people interact with it: from origins, supply chain and pricing to presentation, portioning, packaging, aesthetics and culture surrounding it. Then find a way to twist one or more of these givens, and just like that, you’ve got an innovation on your hands.

Idea 18: Franchises.

Examples: Too many to mention.

Building your own thing from the ground up isn’t for the faint of heart. A lot of people find it easier to buy a franchise to reap the rewards of brand recognition and built-in support. Restaurants, new car dealerships, hotels, and petrol stations are the most popular businesses to launch a franchise.

Takeaway: If all you want is to run your own business rather than some disruptive or niche startup idea, a franchise might be your best option. It gives you a proven method to follow instead of reinventing the bicycle. Or, if you don’t fancy working with somebody else’s idea, consider how your own startup can eventually be scaled up to become a franchise: let people pay you to copy your homework.

Idea 19: A spirituality-based business.

Example: Margate-based Suhaiyla Shakuwra is a Tarot reader and founder of wellness workshop The Art of Being Present. She has collaborated with brands from Selfridges and Soho Farmhouse to Elle and galdem.

Her business was born out of Suhaiyla’s desire to make wellness more accessible and inclusive. And while at first she thought she’d have to change herself in order to fit in, she soon realised that being who she was — black, working class and queer — was exactly what made her unique and interesting. Far from the stereotype of a wellness guru drinking zero-calorie green smoothies in-between meditations, she likes rum and partying.

Takeaway: Don’t feel like you have to conform or fit any particular mould, says Suhaiyla. Your uniqueness is what is going to draw people to you.

Idea 20: An activewear brand.

During the pandemic a lot of people have either got into activewear for the first time or upgraded their existing sportswear wardrobe. 65% of Americans say that they now wear some kind of sportswear in their everyday lives. Whether it’s for improving athletic performance, protection from the elements during outdoor activities, or just as an alternative working-from-sofa outfit, sportswear demand is on the rise.

Idea 21: An independent creative co-working space.

Example: Zen, a network of independent cafés and co-working spaces across Mumbai, Pune and Ahmedabad. Freelance culture has been booming in Indian cities, creating a need for informal spaces offering not just consistently good drinks, baked goods and service but also opportunities for business owners and professionals to make connections and collaborate.

Takeaway: As more and more people choose to ditch office spaces while also escaping the distractions of working from home, there’s a demand for alternative working spaces. Think of all the niches you could explore within that: from freelancers with kids and/or pets to the different needs that various types of creatives might have (and please give me a shout when you open a sound-insulated capsule café for writers).

Idea 22: A small-batch bakery you can run from home.

Example: Kora, a small-batch donut brand. Born out of the lockdown-induced baking craze, Kora only launched in the summer of 2020 — but it now has a waiting list of 10,000 customers. It’s not just to do with scarcity, but also the story behind the brand. Kora is named after the founder’s late grandmother, and the recipes are based on traditional Filipino flavours, some of them from the grandmother’s recipe books.

Takeaway:
Bringing in a person to look after business admin is crucial, says Kora’s founder Kimberly Camara. Having someone on board who knows how to operate a business and negotiate contracts frees you up to focus on things like recipes and ingredient quality.

Idea 23: An innovative watch company.

Examples: Subdial, Dimepiece, the Weiss Watch Company, Hodinkee.

The transition from selling watches in stores to online retail has been incredibly slow, with many established brands still refusing to get with the times (sorry. It felt like the right moment for a pun, oh wait, it just struck me I’ve now done two… er, three. Watch out, I’m on a roll! Four.) This provides an opportunity for disruption, where new brands can create new experiences for watch lovers, from new pricing models to creating pieces that double up as investments whose value grows over time.

Takeaway: Watches are just one of the many traditionally high-end sectors that are stubborn when it comes to innovation. Perfect excuse to get in and rewrite the rules.

Idea 24: Customisable architectural plans and flat-pack cabins.

Example: Den Outdoors. Designed to have minimal impact on their surroundings, Den Outdoor cabin kits were born out of the co-founders’ own love of escaping the city to spend time in the wild. Customers can build their flat-pack cabin themselves in as little as 3 days, or pay a pro to do it. And since the founding husband-and-wife duo Mike Romanowicz and Lizzie Kardon initially just catered to themselves, their priority was people, not profits. Every Den Outdoors design is created to look great, feel great, and withstand whatever nature throws at it.

Idea 25: Creating online games.

Examples: Alexander Hicks, Anne Shoemaker, and other people building games on Roblox. Roblox is an online platform that allows 33 million monthly participants to play games, as well as create their own by using its Studio Software tool. And while the majority of the user base is children, many of them stick around as adults, adding their own games and ideas to the platform — with some studios bringing in 6-figure annual profits.

Takeaway: If you want to build bigger and greater digital experiences, going it alone won’t cut it: you will need to start working with others — says Anne Shoemaker, the 21-year-old gamer-turned-developer who started making games out of frustration when one of her favourite ones had stopped working.

…phew — one quarter done, 3 more to go. If you don’t want to miss those, you can either hit subscribe here on Medium or sign up for my newsletter where I share tips and ideas on personal branding, inventing your own work life, non-sleazy self-promotion, and creative problem-solving.

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Olga Pope

Copywriter and zero-BS brand consultant working with the Fortune-500, startups and entrepreneurs. I get off on helping people who get off on what they do.