The Ultimate Guide to Working in the Gig Economy

Everything you need to know about the gig economy and how to get started in gig work!

Chapter 1

The gig is up… or is it? The rise of the gig economy

Gig work is not new, and it goes far beyond driving for rideshare platforms or delivering food. In its present form, the gig economy emerged alongside the internet, growing sharply during the 2008-2009 financial crisis. In 2019, more than one third of American workers were doing some form of gig work

Gig work offers a chance to earn extra income while the flexibility helps maintain a healthy work-life balance. Gig work also benefits employers, who can lower costs by working with gig employees who perform exactly the tasks needed at any given time.

Enter 2020, and the COVID-19 lockdowns. 

While some gig workers saw demand for their services plummet, others were classified as essential workers. The rise of remote work also resulted in a surge in demand for gig workers skilled in IT and software development.

In the wake of the pandemic, more and more organizations are embracing gig workers. What’s the one key element that’s going to be critical for business success moving forward? Greater integration between independent and traditional employees, so that knowledge can pass freely between them.

In the first chapter of this series, we’ll learn more about what the gig economy is, how it plays a major role in the future of work, and why it’s here to stay. 

What is the Gig Economy?

The gig economy – typically described as work done by independent contractors or freelancers – is not new. Think back to your first job. Did you babysit for the neighbours? Mow their lawns, or shovel snow? If so, you were performing gig work.

For almost as long as people have been exchanging labor for money, work has meant stitching together multiple jobs, doing whatever tasks were available. More recently, in the early twentieth century, staffing and temp agencies began offering a more flexible form of work, and the term “gig” emerged – borrowed from musicians who were paid to perform at live shows, or “gigs.”


When most people think about gig work today, they probably think of rideshare or delivery drivers, and this makes sense, because these workers have been in the news a lot lately. But don’t be fooled; gig work is available in most industries, especially in the public sector.

“Freelancing’s direct impact on the economy is close to $1 trillion, which at nearly 5% of U.S. GDP is comparable to that of a major industry like the information sector.”
– Upwork Freelancing in America Report 2019

There Is A Cultural Shift In The Way We Work

What’s fueling the growth of the gig economy?

The explosion in the gig economy in recent years is due to technology. The modern gig economy was first powered by the internet, which made it simple for people around the world to connect.

At first, people used online bulletin boards such as Craigslist to offer up their services for various types of physical labor. Soon, dedicated platforms emerged, offering a central spot where individuals looking to work could connect with potential employers.

“Tens of millions of Americans have told us that their ‘dream job’ is to work for themselves”
– Mike McDerment, Co-founder & CEO @ FreshBooks

The term “gig economy” really hit its stride in the 2008-2009 financial crisis, which saw a surge in the popularity of task-based labor as rising unemployment drove people to look for any available jobs, even short-term contracts. 

Other factors include the emergence of online platforms such as Airbnb, an online marketplace that made it possible for individuals to commoditize their real estate, and Uber, which transformed the way we get around by employing an innovative and transformative digital platform to connect drivers with passengers. By 2019, more than one third of American workers — 57 million in all — were performing some type of gig or freelance work.


“New digital platforms enable people to earn a livelihood in a way that highlights their individuality. These platforms give providers greater ability to build customer relationships, increased support in growing their businesses, and better tools for differentiating themselves from the competition. In the process, they’re fueling a new model of internet-powered entrepreneurship.”
– Li Jin, Formerly A16Z, defining the ‘Passion Economy’ (a subset within the gig economy)

Benefits of gig work

What’s fueled the growth in gig work? For the people doing the work, the biggest benefit is flexibility: most gig work lets people work when it’s convenient, and this often means earning an income over and above what is received through more traditional employment. Gig work also lets people follow their passions as they develop and enhance specific areas of expertise.


For employers, gig work not only lowers costs, but it also allows staffing to become more precise. In addition, employers have come to appreciate that offering remote work, flexible scheduling, and greater autonomy in how work is done leads to improved work-life balance, which ultimately benefits the organization as much as the workers.

Dealing with the pandemic: the impact of COVID-19

The immediate impact of the COVID-19 lockdowns highlighted many of the inequalities of independent work. Many people turned to delivery options for everything from fast food to equipment for their home offices, and food and parcel delivery workers — classified as essential workers during the crisis — put their own health and safety at risk to keep us fed and working.

“With COVID-19, UberEats have gone up and up but Uber driving fluctuates. It depends on what the level of fear is. ”
– Marvin, Uber and UberEats Driver

Others, especially drivers for ride-hailing platforms and Airbnb operators, have seen their earnings plummet. The economic slowdown has also affected the demand for online labor, particularly in the knowledge economy, as organizations have reduced spending by eliminating every job that’s not essential.

As societies begin to emerge from the pandemic, however, demand for gig work has returned: the Online Labour Index project at the University of Oxford, which tracks the number of projects posted on the five largest English-language online labor platforms, showed a dip in early April 2020, followed by historic high levels of projects in late May 2020. The ongoing transition to remote work also led to a surge in demand for software development and IT services:


Better integration for gig workers

As time passes, it’s also likely that we’ll see that COVID-19 has had another significant impact on independent work. More and more organizations are embracing the benefits of gig employment – in particular, the ability to find and hire specialists who have the precise skillsets needed for specific projects – so the need to better integrate the two types of employment will become critical. Traditional employees and independent workers are often kept siloed within an organization’s structure, and gig workers rarely have equal access to internal knowledge-sharing platforms. This means that instead of flowing freely, information and knowledge get stuck.

With the number of independent workers growing, organizations will need to make sure that processes are in place so that knowledge transfer can continue. Once this happens, independent workers will be better able to put the full scope of their talents to work.

The future of the gig economy

What does the future hold for the gig economy? Even though there are some clouds on the horizon – such as protests and lawsuits over workers’ rights – there is little doubt that developments in technology will continue to change the way people work, and the growing task specialization made possible by gig and independent work means that the age of generalized employment is almost certainly coming to an end.

Chapter 2

The benefits of being a gig worker

The myth of the 9-5 job is wearing thin. If you’re not punching in and out of your job using a time clock, the reality is that your workdays are probably longer than 8 hours. Every time you check your email before leaving for work, every time you take work home to “get a bit more done” after dinner, every time you work through lunch, you’re adding to the hours that you work. But are you being rewarded for this work?

The history of 9-5

The “traditional” 9-5 workday is a relatively recent invention, born in the 19th century. Industrial and factory workers faced brutal conditions, and although calls for reform proposed splitting the day into three parts, with equal time for work, recreation and rest, not much was done. Long working days remained, with workers even enduring 100 hour weeks.
The first real steps towards the modern 9-5 came in 1914, when the Ford Motor Company introduced 8 hour workdays. Although people still worked 6 days, this was a significant advance. The 40 hour workweek only became standard in the United States in 1938.

After manufacturing, workaholism?

In the decades since 1940, and with the growth in white collar jobs at the expense of factory work, working hours have crept back up. By 2014, in fact, the average American worked 47 hours each week. Most people who work extra hours believe that this makes them more productive, and that it’s the best way to ensure that they’ll have a secure financial future. But is this correct? How many of those people working extra hours work at a job where they use a time clock to punch in and out? And does working more hours mean that more gets done?
“When you work in an office, you punch in and out from 8 to 5. I was commuting for 3 hours each day too. I wanted to be able to manage my time and use all of my skills”
– Sandra, Freelancer on Upwork

For most of us, the reality is that working extra hours doesn’t have an upside. Unless we use a time clock to punch in and out, we don’t get paid more. And far from being more productive, we’re suffering more from burnout and lack of free time, so much so that we may not realize that our salaries haven’t kept up with cost-of-living increases, because we simply don’t have enough time to relax.
There’s also lots of evidence that slashing working hours is a better way to increase productivity. A New Zealand company recently tested a program where they gave employees an extra day off each week, with no changes in pay or working hours the other days. The result? Workers were not only happier; they were also 20 percent more efficient. Even in countries like Japan, where long hours are seen as a sign of dedication to one’s firm, there are signs of change: Microsoft Japan ran a project shutting down all its offices on Fridays, and productivity shot up by almost 40 percent over the previous year.

The rise of job-hopping

For millennials – people born in the early 1980s – job-hopping is normal. Even though they’re only part-way through their careers, millennials have changed jobs nearly 8 times on average. For workers, there’s lots of upside to changing jobs often:

Exposure to a wider range of new skills

Chance to gain experience and expand networks

Climb the career ladder faster, especially since many companies favor outside hires for upper-level positions

More opportunities to find what you’re really passionate about

Employers also find lots of benefits in job hopping:

Access the wide range of knowledge and experience that employees with several previous roles bring to their position

Job-hopping employees likely have soft skills that go well beyond specific task-based knowledge

Newly-hired employees are usually eager to make a good impression and don’t tend to take their jobs for granted

New employees’ enthusiasm and higher productivity can rub off on the teams they work with

Gig workers – an essential part of the economy

As people change jobs more frequently, spending less time at each job is becoming more accepted. So is there a connection between the rise of job-hopping and the growth of gig work? Probably. Employers are getting used to hiring people for shorter periods of time, which is exactly what many gig workers look for. But that doesn’t necessarily mean that gig work always means taking short-term jobs: research shows that more than half of all independent contractors have worked with the same company for more than 12 months, and that one third of gig workers also believe that they’ll keep their current jobs for at least five more years.

There’s lots of evidence about the growing numbers of gig workers. An Upwork study found that 57 million Americans did freelance work in 2019 – that’s 35 percent of the entire American workforce. Nearly half – 45 percent – of these workers provide skilled services and labour, filling employment gaps: a 2020 study by the payroll and HR company ADP found that at 40 percent of organizations surveyed, 1 in 4 workers are gig workers.

Why join the gig economy?

For companies, hiring independent workers has many upsides. Independent workers are comfortable with change, so if you’re looking for people who can generate new and innovative ideas, an independent worker could be the perfect choice. Many independent workers have experience working in different roles at different organizations, and millennial gig workers are more likely than other age groups to see themselves as dependable and self-disciplined, to have emotional agility, and to be willing to work hard, all qualities that are highly valued in the workplace.

“From solopreneurs to global enterprises, more and more companies are relying on freelancers to get work done. Partly because you can easily ramp talent up and down in sync with changing work volume. And it’s an easy way to access specialized talent, especially those with in-demand skills.“
– Alexia Nielsen, Upwork

Hiring independent workers can also have financial benefits: companies may see payroll costs drop, because gig workers may be motivated by factors other than benefits and compensation packages. Finally, as outsourcing projects becomes more common, and as companies make hiring independent workers part of their normal course of operations, the demand for gig workers will continue to grow, and more people will choose to supply that work as part of the gig economy.

Gig work by choice, not necessity

Far from being forced to do gig work, most independent workers – 72 percent – are choosing gig work. In fact, only 7 percent of independent workers said that they were doing gig work because they couldn’t find a regular job.

“Self-employed workers enjoy the same overall quality of life as employed workers. The lower satisfaction levels with the material aspects of their job — such as benefits and the stability of pay — seem to be balanced by the satisfaction from greater autonomy and use of their strengths.”
– Intuit Gig Economy and Self-Employment Report

Have you ever noticed that time seems to fly by when you’re doing something you love? Because independent workers can choose their work, there’s a much greater opportunity for them to follow their passions rather than doing boring or repetitive jobs. Here are some other benefits of independent work:

  • Demand for independent workers (especially skilled workers) is growing
  • Work from anywhere
  • Technology is making it easier to find independent work
  • Create your own niche job that makes the most of your talents
  • Schedule your work around your life, instead of the other way round
  • Maintain a healthy work-life balance
  • Find more time for family, friends and hobbies

“Certainly, there is a lot of flexibility which is a huge benefit. Also knowing that the time you put in is the time you choose to put in is a pretty good feeling.”
– Peter Marchetti, Freelance Graphic Designer

Given the increased awareness of the negative effects of stress, is it any wonder that more and more people are choosing to leave “traditional” jobs?

So what’s the takeaway?

Legislation governing 8-hour workdays first emerged because of long hours in harsh factory and manufacturing jobs. As factory jobs become less common, and with the rise in white-collar jobs, working hours have risen once again.

Several studies have shown that shorter work weeks lead to greater productivity and happier employees.

Job-hopping has become an accepted part of the working world, especially for younger employees, and these employees are also the most likely to engage in independent work. For employers, independent workers help increase flexibility and agility. For workers, gig work offers greater work-life balance and a chance to do work that they love.

Chapter 3

Pitfalls to avoid when joining the gig economy

We covered the unique benefits that come with being a gig worker but it’d be wrong for us to only sugarcoat the gig economy. As with most cultural shifts, joining the gig economy has its growing pains.  


Most financial institutions aren’t well equipped to handle the unpredictability of gig income. And the structure that comes with the 9-5 work life may be better suited for some than others. There are various challenged varying from financial to personal considerations that one should be made aware of when deciding if gig work is right for them.  


In this section, we’ll provide an overview of 7 challenges that most gig workers face and a checklist of questions that will help you prepare on how to become a gig worker. 

The types of work done in the gig economy often dictate that gig or independent workers have specific financial needs. By its very definition, gig work can be irregular and unpredictable, and gig workers frequently receive pay from more than one source. As a result, gig workers’ income is also unpredictable, they rarely receive stable or regular paychecks, and they may have multiple sources of income. Because regular income is a primary qualification for accessing credit, many gig workers have little credit history.  

A 2019 study by Upwork found that 53 percent of American workers ages 18-22 work in the gig economy. For these members of Gen Z, who are just starting their professional lives – will their gig job mean they can’t easily take out a car loan, or get a mortgage? Will their choices now have a lasting impact on their ability to access financial services later in life?  

Some gig work challenges are well known… 

The most common challenges facing gig workers—and these have been in the news recently, due to the impact of COVID-19—are an inconsistent income and the inability to access employer-funded benefits programs.

Inconsistent, unpredictable income:

When the pandemic hit, many rideshare drivers saw demand for rides disappear. Independent workers earning an income through property or vacation rentals were similarly affected. On the other hand, independent workers on food delivery platforms were so busy that they were classified as essential workers in many jurisdictions and were exempt from lockdown orders. Skilled IT workers also saw demand for their services soar as many organizations shifted entirely to remote work. 

No access to employer-funded benefits:

Most independent workers have no access to employer-funded pensions or retirement savings plans. Unless they’re covered by a spouse or partner’s plan, independent workers must also purchase their own health insurance, as well as any additional insurance needed in the course of their work.

…And some gig work challenges are less obvious 

Here are some additional challenges that many gig workers face: 

Difficulties getting paid:

Gig workers, especially those who work perform skilled work through platforms such as Fiverr, Upwork or Clevertech, sometimes struggle to get paid on time or paid in full. Add in the complications of working at a distance—international currency transfers, cross-border banking fees, and communications challenges—and gig workers may find distance is a very real barrier to getting paid. 

More complicated finances:

Many gig workers receive pay from several clients or work on several different platforms. They may thus be paid both fixed fees and hourly rates and must track their income to account for both. Without an employer deducting taxes and benefit payments, gig workers must also handle these on their own.

Fewer banking options:

Gig workers must often manage all their finances—both personal and business expenses—using a personal banking account, without the benefit of a bank account geared towards small businesses, and the additional services those accounts offer. 

May not be eligible for government programs aimed at gig workers:

This might sound surprising, but when the U.S. government launched special unemployment insurance programs for gig workers in the wake of COVID-19, gig workers who had earned any income from a traditional job in the previous year found they were ineligible to receive funds, even if most of their income came from gig work.

Losing the benefits of gig work:

Recent legislation aimed at protecting the rights of gig workers by changing their employment status from independent contractors to employees may end up making gig work much less flexible.

Thinking about gig work? Consider these questions first


Are you planning to work part-time in the gig economy while keeping your traditional job? If so, don’t forget that you’ll be required to pay taxes on your gig earnings. Will your extra gig income push you into a higher tax bracket?

Self-Employed Doesn’t Mean Working Alone

Most U.S. freelancers agree that success in the gig economy depends as much on soft skills as on technical skills, and networking and marketing are essential to building a career in the gig economy.
“Certainly, there is a lot of flexibility which is a huge benefit. Also knowing that the time you put in is the time you choose to put in is a pretty good feeling.”
– Peter Marchetti, Freelance Graphic Designer

Taking on different roles

If you just want to focus on doing one thing, and one thing only, gig work might not be the best choice. A 2019 survey shows that gig workers spend just over half their work time (53%) doing billable work. The rest is split between building their business (25%) and administrative work (22%).

What is the gig economy lifestyle for most people? We’ve highlighted the advantages and disadvantages below:

Gig work – the advantages

  • Flexibility, including the ability work from anywhere, at any time, and to manage personal circumstances that might make traditional employment difficult

  • Greater work-life balance and the option to follow a schedule that lets you spend time you’re your family or friends, or pursue your passions

  • Autonomy, including the ability to pick and choose what work you’ll do

  • Freedom from office politics

  • Technology is making it easier to find work in the gig economy

  • Harder work = higher income (usually)

  • Working with multiple employers may offer greater income security in a tough economy

Gig work – the disadvantages

  • Unpredictable workload = unpredictable income

  • Not all gig work is equal, and skilled gig workers with specialized skills usually earn much more than rideshare or delivery drivers

  • Gig workers in the platform economy may need to work more than full-time hours to make a living

  • Gig workers may have trouble accessing credit

  • When you’re the company, it’s not always easy to take time off or turn work down

  • No team members to help with high work volumes

  • No support staff to help with administrative tasks

  • No benefits

  • Need to withhold some earnings to pay taxes and government benefits

  • Need to manage your own retirement savings

Gig workers have unique financial needs, and these needs are not always met by traditional financial institutions. Younger gig workers may find it harder to access credit when they’re ready to make more substantial purchases such as a car or a home. Gig workers often face challenges getting paid and may not have access to tools and resources that can help manage their finances.

In addition to an unpredictable income, most gig workers have no access to employer-funded benefits or health insurance. They must also save on their own for retirement.
While some gig workers earn much more than the average, others end up working for much less than minimum wage.
The flexibility and autonomy of gig work can sometimes be a trap, especially when taking time off means losing income. 

Many gig workers must perform work well outside the scope of their actual job, including marketing, networking and administrative work, and they must do this without additional support.

Chapter 4

Planning for your future in gig work

Are you looking to put in full-time hours as an independent worker? Maybe you want to supplement a traditional job and earn some extra income with a side hustle? Whatever your goals, there’s a gig job out there to meet your needs.

Want to learn more about the different types of gig work? We describe some of the popular options below.


Ridesharing is a popular entry point for gig work. If you have a good driving record and access to a newer vehicle that’s in good condition, you’re all set. The big names are Uber and Lyft, but if you’re looking for something a little more personal, there are also some smaller regional platforms out there.

For drivers, there are lots of benefits to ridesharing. It’s hugely flexible, so you can fit it into your life. Work a part time job in the mornings? You can drive in the afternoons, for sure, but you can also pick up rides on your way to your other job. You’d be going there anyway, so why not earn some extra cash? You can also take time off when you need to – just don’t log in to the app. You’ll never need to get your shift covered if you’re sick or don’t feel like working.

Here’s how one rideshare driver describes the job: “The thing I love about this side job is the flexibility that I have with it. I’m not required to be anywhere. There is hardly any other part-time job in the world where you can work or not work, literally whenever you want.”

These are some key points that can help you get the most out of ridesharing:

Learn where the demand for rides is highest and wait nearby. Don’t drive around – you’ll just be spending money on gas.

Avoid traffic when you can. You’re getting paid by distance travelled, so getting stuck in traffic drives your hourly rate of pay down.

Consider driving for more than one platform. If no-one needs a ride on one, try another.

Understand how the apps work, especially surge pricing.

Consider using a third-party app, like Sherpashare, that can help maximize your rideshare earnings. Look online for an option that meets your needs.

Investigate the insurance coverage provided by the platform(s) you drive for, and consider topping up your own coverage if necessary.

Keep your car clean, provide phone chargers, consider offering some basic amenities like gum, tissues, or bottled water.

Take regular breaks. They’ll help you stay alert and refreshed.

Don’t forget that running costs for your car (gas, fluids, regular maintenance) will eat into your earnings.

Above all – drive safely.

Food delivery

Just like ridesharing, there are lots of different food delivery platforms – everything from big international platforms like Uber Eats and Doordash, to platforms like Instacart that specialize in grocery deliveries, platforms that are smaller and focus on a specific city or region, and even platforms that only deliver to specific customers – usually college and university dorm rooms.

If you don’t want to drive, food or grocery delivery can often be done on foot or on a bike, especially in urban areas. But if you’re trying to work a food delivery job as a side hustle, be aware that there are two main periods of demand each day: lunch and dinner. If you’re not going to be available at these times, food delivery might not be your best option for gig work.

Here’s what an Uber Eats driver likes about food delivery work: “I find working for Uber Eats to be a refreshing change of pace from driving passenger. Since most deliveries are only a few miles, I’m able to stay close to home or a certain area if I only have a limited amount of time to work. Other pros of delivery work include not having to keep a clean car, being able to drive how I like and also being able to listen to podcasts or talk to friends and family while I’m driving. Customer interactions on deliveries are usually less than 30 seconds so if you’re not a people person or just not in an outgoing mood on this particular day, this can be a good option for you.”

Here are some tips that can help maximize your food delivery earnings, and other important points:

Sign up with more than one platform.

You’ll earn more delivering larger orders. Also, be alert to the possibility of stacking orders – picking up two or more from the same restaurant.

Pay attention to promotion platforms, such as completing X number of deliveries in a shift. You can really pad your income this way.

Give your customers a heads up when you’re nearly there. If you’re in a car, take a few seconds to get out and hand them their food directly – it boosts your chances of getting a tip.

If you drive, investigate the insurance coverage provided by the platform(s) you drive for, and consider topping up your own coverage if necessary.

Pay attention to maintenance costs for your car or bike.

General and skilled services

General and skilled services include lots of different types of gig work. One of the biggest platforms is Upwork, which matches clients and freelancers in fields including web and mobile development, graphic design, writing, administrative work, customer service, marketing and accounting. is a platform that lets businesses fill short-term staffing gaps with skilled workers: positions commonly posted on the site include bartending, serving, retail work, event staff, and brand ambassadors for trade shows. For gig workers interested in caregiving, is a platform that lists positions including elder care, childcare and tutoring, and pet care, as well as housekeeping and cleaning.

If you’re just starting out as an independent worker, or are looking for a job with flexible hours that can help you hone the skills you need for a great career, consider a platform like Upwork: “What’s great about Upwork is that when you view a job listing, you can see the other (past) jobs that particular client has hired for. So when you’re starting out, a good strategy is to target clients who consistently hire on the platform. For example, if you’re a graphic designer, try to find a client who has a record of hiring people for graphic design projects.”

Want to find a gig job that matches your skills and interests?

Be specific about the work that you’re going to do. If you’re bidding for a project on Upwork, make sure your proposal hits the key points the client is looking for. Answering a job ad on Make sure you’re willing to perform all the services needed. Posting your services on Be specific about what you offer, so no-one is disappointed.Be clear about the amount of work you’ll be doing and how you’ll get paid. Will it be a flat rate, or an hourly fee? If it’s an hourly fee, make sure you’re earning a reasonable wage for the project.Don’t take on more work than you can do. Rather than running yourself ragged and risking missed deadlines, it’s better to excel at fewer jobs, especially at the beginning, and work to build up a stable client list.

Working multiple gigs

One of the great things about independent work is that you’re free to do as much – or as little – as you like. Some gigs fit naturally together: if you’re driving for Uber, adding Uber Eats is an obvious way to earn more, especially since the platforms make it easy to accept rides and deliveries at the same time.

Also, don’t rule out the possibility of doing different types of independent work: this can help keep your income steady if jobs on your main platform dry up (as rideshare drivers experienced during the Covid-19 lockdowns), and it can help inject some needed variety into your days. If your main job is doing web design through Upwork, for example, but your biggest client hits a dry patch, a side gig doing something totally different – like dog walking – helps pay the bills, and as an added bonus, it gives you a great reason to get outside and get some exercise.

Here are some other tips to consider when working multiple gigs:

Take advantage of the flexibility of independent work and schedule regular hours (or days) off, to give yourself a chance to recharge.

Manage your work time carefully so you don’t miss deadlines, especially when you’re working for different clients or on different platforms. There are lots of free project and time management apps available, or you could go old-school with a paper planner. Find a system that works for you and use it.

If you’re regularly working on bigger or more involved projects, schedule regular check-in points with your clients to make sure you stay on track.

Every gig worker needs a system to stay on top of the work that they do, and at the top of your time-management to-do list should be scheduling time off work. Independent work is flexible, so make sure you take advantage, and schedule regular hours (or days!) off, to give yourself a chance to recharge.

Consider using a financial literacy app to help with budgeting and saving, especially if you’re just starting out with gig work.

Track your earnings carefully and pay attention to tax brackets. If your side gig pushes your total income into a higher tax bracket, you may see less benefit from all your hard work than you were expecting.

Is gig work right for you?

If you’re looking for a flexible job with lots of variety, gig work may be a great option. You can work as much or as little as you like and fit your work around your life, leaving more time for family, friends and hobbies.

If you don’t feel like your current job is leading towards a career that you’ll love, gig work also lets you try out a new job without commitment, and while letting you keep some income coming in while you consider different options.

Finally, if you’re looking for a way to earn some extra income, there’s a gig job out there that will fit your skills and your schedule.

Ridesharing, food delivery and general / skilled services are three of the most popular forms of gig work.
Many independent workers find that working for more than one platform is a great way to earn more money.
Keep track of jobs and projects carefully so you don’t miss deadlines. And schedule some time for yourself – you’ve earned it!

Chapter 5

Logistics of becoming an independant worker

You landed your first gig – congratulations! But what happens next? After the job is done, how do you make sure you get paid for your efforts, and how do you build your business, so the work keeps coming?

Domestic payments

If you’re working through a platform, you’ll usually get paid through the platform. On some, especially ridesharing and delivery platforms, you’ll be paid as soon as you finish a job. Others pay on a weekly or monthly schedule. This is convenient, but don’t forget that the platform also deducts a percentage of your earnings (usually between 5% and 20%) as a fee.

You might find that some customers or clients will encourage you to accept payment outside the platform. This could be tempting – especially when it means you aren’t paying that fee back to the platform – but it’s a bad idea. First, accepting payment outside the platform means you risk getting kicked off the platform. Second, if you’re a rideshare or delivery driver, accepting payment outside the platform could invalidate any insurance coverage they provide. And third, if you accept payment through PayPal, and there’s a dispute about your work (or your client claims that there’s a problem, even if there isn’t), you’ll likely lose. In this scenario, your client is the customer, and PayPal tends to favor customers when there’s a dispute.

What happens if you’re a freelancer and you’re not working through a platform? If you’re building up your profile and doing freelance work for your own clients, you’ll need to handle your own billing. Here are some important steps to follow:

  • Get a deposit – even if the job is tiny. In many fields, 50% is a good number to start with.
  • Use a contract, and make sure that it clearly describes the work to be done, the deadline (and any check-in points along the way), the payment you’ll receive, and any late fees you’ll charge.
  • Check references and do credit checks. Especially for new clients, look on their website for lists of their clients, and give them a call. You’ll soon get a sense of whether this is a company you’ll be comfortable working with.
  • Have a plan for how you’ll deal with late payments.

International payments

Many freelancers working internationally still receive payments via wire transfer, and these transfers are often in one of the major international currencies: the euro, the British pound, or the U.S. dollar. In addition, international freelancers often must wait to get paid, and when they do, they’ll have to handle currency conversion on their own.

One of the advantages to doing independent work through a platform is that international payments get processed through that platform. In most cases, cross-border payments will be transferred to workers on a regular basis (weekly or monthly), and currency conversion will be handled by the workers’ banks.

Here are other some ways to ensure that you get paid for your work, quickly and in full:

  • Use an online payment option. PayPal is an obvious choice, but make sure you look at the fees and compare them to some of the other options out there.
  • Use an app or platform that can handle invoicing, like Due or Zoho. Send out invoices on a regular schedule – weekly or monthly. Look for platforms that can help with this – as a bonus, many of these also offer features like recurring payments for regular clients or sending past due notices.

Building up your profile

Here are some tips and best practices that can help you earn more as a rideshare or delivery driver, even when you first get started:

Tips and best practices that help you earn more as a rideshare or delivery driver, even when you first get started
Read more for ways that freelancers and skilled independent workers can build their profile quickly
Tips and best practices that help you earn more as a rideshare or delivery driver, even when you first get started

  • Know when the demand is highest, and make sure you’re working at those times. For Uber drivers, that means driving when surge pricing is in effect. For food delivery drivers, think lunch and dinner.
  • Sign up with more than one platform and maximize your chances of staying busy.
  • Track all your expenses so you can maximize your deductions at tax time. There are also apps designed for rideshare and delivery drivers that can help with this (Sherpashare is one).
  • Pay attention to promotions, like completing X rides in a week to earn a cash bonus.
  • Refer your friends to the platform and earn a bonus when they sign up.

Read more for ways that freelancers and skilled independent workers can build their profile quickly

  • Be specific about the work and services that you perform.
  • Develop a portfolio with samples of your work. If you haven’t had any paid work yet, see if you can do a job as a trial.
  • The best way to promote yourself is to do good work. Before you start working, make sure that you clearly understand what your client is looking for, and maintain communication with clients throughout the job.
  • Don’t let problems go unsolved.
  • Finally, take a hard look at your rates. When you’re starting out it might be tempting to set your rates low, just to attract more potential clients. But ask yourself, are these the type of clients who are always going to pay up on time, every time? Setting rates that are fair is the first step towards building a great freelance business. Once you have regular clients, you can consider offering them a subscription discount as an incentive to sign up for your services over a longer period (pay for 11 months, get the 12th month free).

Why should you care about reviews?

As a rideshare or delivery driver, do your best to give your customers great service – this boosts your chances of keeping your rating high. Drivers can get kicked off Uber if their rating falls below a certain level, so this isn’t something you want to ignore.

As a freelancer, the best way to earn a steady income is to have regular, repeat clients, and having good reviews is essential to gaining this kind of customer base. Follow up with clients after the work is completed and ask for a testimonial. You can even offer to draft a short testimonial on their behalf and send it to them for approval. And don’t forget to ask your clients to recommend you to other people they know who could use your services!

If you’re getting gig work through a platform, you’ll usually get paid through the platform. This means you’ll have a better chance of being paid in full and on time, but you’ll almost always pay for the convenience.
International freelancers often deal with wire transfers, especially if they aren’t working through a platform. There are also several payment and invoicing apps that make it easier for independent workers to get paid.
Whether you’re a rideshare / delivery driver or a freelancer, building up your profile is a great way to earn more money right from the start. And don’t discount the importance of getting great reviews: they are a key part of finding success in the gig economy.

Chapter 6

Learnings from Independent workers who have found success

From rideshare driver to full-time blogger

One of the most prominent gig work influencers is Harry Campbell, aka The Rideshare Guy. Campbell had a day job as an engineer at Boeing when he first started working as a rideshare driver part-time. In 2015, however, he quit his day job to work full-time as a blogger, writing mostly about ridesharing and delivery gigs, and offering up valuable tips and hints to his readers. Now, Campbell runs a mini-empire based on the gig economy, has hired writers and web designers for his site, and earns income through driver referrals and brand partnerships. 

For Campbell, the decision to start blogging full time was “kind of a no brainer.” He was giving up a lucrative day job, but in exchange he was doing something he’s passionate about, and he was helping people as well:

“Whether it was a tip to make more money, advice on being a better driver or just advice on how to enjoy what they do a little more, this site has helped a lot of people and my goal is to continue helping as many people as I can.”

Sharing the delivery experience through YouTube

Another well-known gig work influencer is Kaylania Chapman, The Blessed Driver. Chapman has experience with several gig platforms, including Instacart, Amazon Flex, Amazon Fresh, Doordash, and Uber Eats, and shares tips and advice for people interested in doing gig work.  

Chapman also has experience advocating for herself: in 2019 she was one of the Instacart workers who complained about missing tips, which quickly resulted in a turnaround from the platform. She urges new gig workers to pay attention to critical reviews for gig jobs that might stand out as red flags, and reminds workers that the referrals program, which might look like an easy way to boost your earnings, is almost always a one-time payout. On top of that, referrals can lead to over-saturation, with more drivers than the market can support. That one-time payout could end up costing a lot in the long run! 

Above all, Chapman is open about the fact that while she’s found success doing gig work, ultimately, she’s sustaining herself on somebody else’s platform. She might be doing independent work, but she’s not a business owner, and she’s not an entrepreneur. Chapman advises gig workers to “know your season and know when to seek other opportunities”. 

When apps launch in a new area, they attract a lot of attention, and everyone signs up. Pretty soon, the well runs dry. Chapman suggests having a firm goal when starting gig work, and rather than just doing a job until there aren’t enough orders, do it until you’ve reached your goal. This may mean doing different gigs at the same time, and if the work has slowed down in your market, turn to something else. 

Writing about the inequalities of freelance work

Navneet Alang is a freelance writer in Toronto, and while his focus is technology and culture, his work often highlights the inherent inequalities of gig work. During the pandemic, for example, Alang followed advice to get his groceries delivered, and was struck by the realization that he was getting his food only because someone else – an Instacart worker – had taken substantial risks on his behalf.  

A recent opinion piece by Alang points out that while skilled freelancers can earn a substantial income doing independent work, some delivery or rideshare drivers earn minimum wage, or less. Alang also explains that the typical gig worker status as “independent contractor” means that gig workers aren’t eligible for many elements of the social safety net, which works on the assumption that people are either employed, and have benefits through their employer, or are not working, and thus must depend on social assistance. Gig workers fall in the middle: working, but without benefits. Alang values the freedom that comes with being a freelance writer but feels that Canada is still falling short of the mark when it comes to ensuring that independent workers also have access to the collective social safety net.

Looking to the future: will Uber lead the charge to a new way of working?

In a recent opinion piece in The New York Times, Uber CEO Dara Khosrowshahi stated firmly that gig workers deserve better, and that this isn’t simply a matter of paying them more – it means creating a new way for gig workers to work. Gig workers have the freedom to fit their work around their life, and for many, this freedom is the reason why they’ve chosen not to have a traditional job.  

But Khosrowshahi also recognizes that the freedom of gig work also comes with a big downside: if gig workers aren’t working – whether that’s because they’re taking a vacation or they’re in the hospital – they also aren’t earning any money, and they likely aren’t receiving any benefits (like vacation or sick pay) either. Khosrowshahi is calling for a “third way” for gig workers to work, one that lets them retain the independence they value, even as they receive more benefits from the people they’re working for. 

Chapter 7

Additional resources to get you started

Co-working spaces offer scope to grow your gig business

For anyone considering gig or freelance work in fields such as accounting, writing, proofreading, photography, graphic design, or web design, coworking spaces can give you access to the office space you need to build your gig business. Depending on your budget, you can choose from a range of options such as shared workspaces, dedicated desks, and even private lockable offices. Most coworking spaces will also let you book meeting rooms, ideal for client meetings. Many will also offer extra features such as mail services, high-speed internet, and coffee bars. Some even include access to outdoor space – perfect for taking a break on a nice day.

Another advantage of using a co-working space is networking. If your gig job relates to finance, consider a co-working space in the financial district where you’ll bump shoulders with professionals at larger firms. If you do creative work, look for a space that caters to entrepreneurs or small businesses in a similar field. As an independent worker, you’ll need to handle your own marketing and sales, and making connections with people in your industry is the best way to do that.

Track expenses to maximize your gig earnings

As a gig worker, you’ll file taxes as an independent contractor, and tracking (and claiming) your eligible expenses is an essential part of your business.  

  • Rideshare and delivery drivers: track your mileage, fuel, maintenance costs, and other related expenses. 
  • Freelancers doing skilled work: track any expenses related to your work. This includes your computer, software, cell phone, and any other equipment you need (such as a camera, 3D printer, or scanner) You should also be able to claim the rent for your office or coworking space, and if you work from home and pay rent, you can also claim a percentage of your rental expenses, as well as your utilities (hydro and internet access). 

CRM and other tools make gig work easier

Customer relationship management applications – CRM – are an essential part of the independent worker’s toolkit. The right CRM can help you set up and manage client meetings, contracts, bookings, invoices, and payments. Many CRM platforms also offer communication tools, perfect for keeping in touch with former clients and building relationships with new ones, as well as collaboration software that ensures projects stay on track. Other features you may want to look for include schedules, timers, and the ability to sign electronic documents securely. 

Are you a gig worker doing in rideshare and delivery work? Don’t discount the benefit of CRM tools and utilities. Tracking your hours and expenses makes it easy to calculate your hourly wage, and being able to generate and manage bills, invoices and contracts is essential f you want to work beyond the platform economy. Keeping track of contacts also makes it easier to turn your side hustle into a full-time business. 

In addition, CRM tools can be invaluable when your business grows, and you need to hire additional gig workers to help handle the load. There are tools for hiring, reference checks, training, scheduling, and communications. Even larger organizations use talent management platforms that let them work with freelancers by treating them as third-party vendors or managed service providers, and making it easy to hire, train, and schedule. 

Think outside the box

One of the biggest benefits of independent work is freedom: freedom to choose which work you’ll do, and when, and freedom to branch out into new ventures. One area that’s received a lot of attention lately is subscription-based content. Platforms like Patreon let artists and other creative professionals earn a regular income and engage with their audience by sharing exclusive content, podcasts, tutorials, and interviews. Putting high-quality content on platforms such as YouTube and Instagram can also result in income when your number of followers grows.