Work & Money

7 big problems freelancers face and how to manage them

Tips for finding success and happiness in the gig economy.

Tips for finding success and happiness in the gig economy.

(Credit: iStock/Getty Images)

In late 2019, after freelancing for over three years, I found that working for myself got really, really hard. My anxiety skyrocketed, I procrastinated almost everyday, and I just couldn't get into a good groove. This all led me to feeling pretty darn useless and, full disclosure, to not making much money. In fact, my salary was the lowest it had been in over ten years.

When it comes to freelancing though, I know I'm not alone. As a journalist who gets invited to many events, whenever I see a colleague, there are often a few minutes of commiseration on how our industry is doing (layoffs, closures, etc., have become regular conversation topics), as well as how freelance life is sometimes good, and sometimes bad. 

"The whole concept of what is a career has been really thrown up into the air," remarks Dr. Jennifer Newman, a Vancouver-based workplace psychologist, who notes that this idea alone can be really disconcerting for people. 

"The inherent nature of freelance means everything is on you, which can be extremely freeing but also absolutely crippling," admits Emma Yardley, an award-winning travel writer. And though Yardley says she loves working on her own, it can still be tough. "I was recently diagnosed with generalized anxiety and it's taken me years of practice – and a solid year of cognitive behavioural therapy – to mitigate some of the anxiety that comes with this topsy-turvy gig."

Over the holidays a friend mentioned that the law firm where she works was renting out two desks, and it was at a location that was super easy for me to get to. I decided to take the leap and rent a desk as a jumping off point for a hopefully more prosperous 2020. And, while this arrangement won't cure all my gig-economy woes, just being around people and having somewhere to go feels really good right now.  

But I knew I needed to dig a bit deeper, so I spoke to Dr. Newman to learn why we feel certain ways about working for ourselves, how to improve our sense of control as freelancers, how to avoid distraction and more. I also tapped into my network of freelance pals to learn some tips on how to make this freelance life actual #lifegoals. These tips should help you with figuring out how to navigate those wavy gigging waters. 

How to avoid burnout

As Dr. Newman defines it, burnout is "having lots of work and lots of responsibility and no control." And this can lead to pretty conflicting feelings about the state of your career and whether freelancing is right for you in the first place. "The irony of the situation that people find themselves in is that being self-employed, they have a lot of control, but also not a lot of control. Ultimately, you can control when you work. You can control the volume of work, once it gets going, of course." But getting down to it, a successful work life is about how you look at the amount of work you do, the type of work that you take on and figuring out when you're going to actually put in all those work hours, she says.

Dr. Newman recommends giving yourself some structure. If you're fielding consultancy gigs and referrals from colleagues, especially if you're fresh to freelancing, be realistic about when and how you want to work. Dr. Newman says to look at things like, what time of day do you work most efficiently, what time works for you in terms of life circumstances, and how many hours per day can you actually be productive. "And then finally," she continues, "what's the type of work, because there's some work that would not be worth your while." 

Types of work that might be of value to you include: what's good for the bank account, what's good to keep the creative juices flowing, and what's good for the exposure. How you balance them out will depend on your current needs and goals. Constantly reflecting on these ideas may seem daunting at first, but once you get into a groove, it will start to come more naturally. 

How to avoid feeling isolated

"I live alone and I work from home," says Toronto-based freelance writer and editor Randi Bergman. "I feel sometimes like I'm in the Twilight Zone. Like I'm in my own little world."

"I really like working on my own — I always have," says Yardley. "Do I miss the camaraderie of being part of a group passionately working together on a common project? Absolutely, but that's different than feeling isolated." 

Yardley says she taps into social media groups, her emails, and spending time with her beloved pets during the work day to keep her from feeling lonely. "The nature of my work trips means I'm actually surrounded by other journalists and public relations pros a good 25 per cent of the time," she adds.

Dr. Newman does see loneliness as an issue for those working from, "because you do decrease your contact with colleagues." She also notes that feelings of increased competition amongst your former co-workers, who may also be taking part in the gig economy, can lead to the perception of being in it all alone. 

One antidote she suggests is "forming a professional network of people with complementary skills, and you can use each other as a referral base... help each other with overflow." Simply getting together once or twice a week to work with your computers next to each other can also help. "That can be a nice way to cross-pollinate and keep ideas going." Don't forget to look into doing workshops, conferences, etc., in your field as a way to keep connected. When you're working in an office everyday, these types of things tend to come to you, so you definitely have to put in a bit of effort here. But the payout is worth it. 

How to avoid procrastinating

Sometimes the simplest solution can be the most productive. "One of the ways I've seen people handle [procrastination] is by creating deadlines," says Dr. Newman. The psychologist recommends making the most of your smartphone calendar, or even a day planner, by scheduling everything from meals and workouts to emails, meetings, work time and time to brainstorm. Breaking bigger tasks into smaller bits and adding them to your calendar can help stave off procrastination and actually spark some creativity, and that's "the beauty of making a schedule," says Dr. Newman. "The most deadly thing is when you have a whole day unplanned."

"If you know what you're going to be doing the next day, it can also trick your mind into going, 'Oh, yeah, there's plenty of work that I have to do. I'd better get going,' as opposed to days stretching out endlessly," she adds.

But don't be too hard on yourself if some days you're just not feeling it. "Allow yourself to change up what you're doing," Dr. Newman continues. "That's the beauty of being your own boss. You say, 'You know what? What do I really feel like doing today? Oh, I actually feel like doing research.'" If it's research or brainstorming that's getting you excited, dive in, and schedule other work until a bit later in the day or the next day.

Also be mindful of how you talk to yourself during the day. Instead of chastising yourself by saying things like, "I should do this and I should do that," Dr. Newman says to recognize those thoughts, feel those feelings, and then take a minute or two to refocus by trying to think about what's next. 

If that doesn't work she suggests you take a few deep breaths or a little walk about the house, and try not to let negative chatter deter you from focusing on the task at hand. When you've noticed that you're distracted, "return gently, and then go back to the breathing," she suggests. "And you might find yourself doing that over and over and over again in the space of five minutes even. And then that brings you back to your work and to what it is you actually want to do. What happens is people can enter what they call a flow state," where you get into a good groove with work, where the world falls away and you're honed in on the task at hand.

How to avoid anxiety around money

Creating a budget can certainly help us feel less financially stressed, but that's not the only way to avoid feeling a certain way about your cash flow. 

"My general motto as far as finance is, I'm not frugal, but I'm not an idiot," says Bergman. "I'm sort of somewhere in the middle. I don't buy anything I can't really afford. But at the same time I don't say no if my friends invite me to do something." Bergman, who uses an app called Wave to track her invoicing, says that it's taken her three years to get a handle on her finances, which can go up or down by $5,000 to $10,000 each year. "The first few years I was freelance, I had no idea [what to expect]. Because every year is different, random things come out of the blue." 

When it comes to practical ways to avoid financial stress, yes, Dr. Newman recommends a proper budget. "On a very structural basis, there's creating a budget for yourself," she notes. "It's really key, including creating a savings aspect of the budget. Even if it's a small amount, psychologically it does wonders." Working towards a three-month buffer in your savings account, for example, is a good goal and would offer peace of mind in case something prevents you from working for a bit or if you simply want to feel like you can take some time off every now and then. "And you won't have that right off the bat necessarily, but that would be part of this whole intentionality in terms of goal-setting." 

Your financial admin process doesn't have to be too complicated. "Figure out what works for you and be OK with it," suggests Yardley. "I really wanted to use one of those colourful invoicing apps and integrated budgeting tools because I thought they looked cool, but I just kept going back to a simple Excel spreadsheet and plain old PDF invoices. I keep clear records and I get paid, that's all that matters."

Sometimes being super diligent with your finances may be its own cause for anxiety, but if you're on top of things, Dr. Newman believes seeing this bigger picture can help keep anxiety at bay in the long run. "Be kind of gritty about this, right? 'What am I spending, and why am I spending it, and how is this helping or hindering me right now?' Those are very important things to look at," she says.  

The idea of 'what happens if this all stops' can be very daunting, but Dr. Newman says those feelings do decrease with time and she recommends keeping one foot in front of the other, citing the Field of Dreams adage that "if you build it, they will come".

How to motivate yourself

Motivation is what drives people to succeed. But don't think that this only comes from within. "If you have the funds, go see somebody who does coaching or development," recommends Dr. Newman. "When I work with people around this, it's basically creating a mini strategic plan, and you have somebody as a sounding board to talk to you about it. I think it's worthwhile. It can be a line item in your budget, and it can help people stay motivated." 

Self-talk can also play a role in how we keep the passion going for our work. If you're working in an area that you've lost interest in, you'll start to think of work as a grind, says Dr. Newman. And people often think they can't let go of certain types of work, because that work is what's paying their rent. "When that happens to you, you can take a very gradual approach" to shifting gears, she suggests. "You can say, 'I'm going to keep doing these things, but I'm going to do a little bit less of them.'" It may take three to six months to figure out how to manage moving into a more interesting sector of work, but give yourself permission to transition slowly, as opposed to going cold turkey and throwing everything into a tizzy. "You have to be willing to allow yourself to change," she continues. We're not working for the same company for say, 35 years anymore, so we need to be easy on ourselves when making any sort of career adjustments. 

"To go full-time freelance, you have to like what you do or it won't work," says Yardley. "When I get in the writing zone, the challenge is forcing myself to stop and take breaks rather than motivating myself to get working—but that doesn't happen everyday." To keep motivated, she'll only respond to emails at the start or the end of the day, she keeps social media as a lunchtime or after-work endeavour, and, if after sitting at her desk for one hour she hasn't put any words down on her screen, she'll start to work on something else. "About 85 per cent of my job is administrative (pitching, scheduling, invoicing, researching, etc.), so there are always other tasks to do."

"I find that writing requires a certain type of concentration that I don't have until four o'clock in the afternoon, which is really sh**ty because my brain is the most on at 7 p.m. or 6 p.m.," Bergman states. "On one hand I try to embrace it, and on the other hand it doesn't necessarily work that well because I have commitments at night sometimes." Bergman knows that a freelancer schedule will never be perfect. But if she has a meeting at peak inspiration time, she tries to tweak her timing slightly by starting to write a little bit earlier in the day, as opposed to getting into a groove and then having to leave for a meeting. 

How to manage your time effectively

Time management, as mentioned above, can help set the stage for success in the gig economy. But don't forget to include even mundane tasks to help you create a realistic day-to-day schedule. "Build a schedule that includes your eating and your exercise and when you're sleeping," suggests Dr. Newman. And, similar to what Bergman mentioned above, consider when you're at your optimal level for work. "Everybody has a rhythm, right? Some people are night people. Some people are morning people. It just depends. So when is the best time for you to work?" relays Dr. Newman. 

Bergman says on most days she works out first thing and then uses part of her morning to get organizational stuff done, like meal prep and tidying the apartment, to get them out of the way. Then she settles into emails and writing. 

For Yardley, it's different. "There's the fear you won't find work, fear you'll lose the work once you've found it, fear your work isn't good enough, and the fear if you don't answer these 32 emails by 11 p.m. on Saturday night your whole career is over," she says. "The best thing I did for my mental health was to turn weekends back into weekends.There are, of course, some exceptions. But now when a big assignment comes in unexpectedly on a Friday with a Monday deadline, I say yes because I want to do it – not because I feel I have to or the world will implode. I'm still working on feeling comfortable enough to take a full two weeks off, but baby steps…" 

Regardless of how exactly you choose to lay out your schedule, setting solid organizational boundaries around your time is really important here. 

How to set long term career goals for yourself 

One common conundrum amongst members of the freelance community seems to be goal setting and long-term strategizing. When you're settled into a corporate groove, those things are frequently built into the culture. For freelance life it's best to think of strategy in a bit of a shorter time frame, says Dr. Newman. "Start with looking ahead one year," she says, "and then go to three, and then go to five, and then go to 10." 

"The other thing is to recognize everybody has a career development life cycle," notes Dr. Newman. "What that means is you have early career, you have mid career, you have late career, and then you have pre-retirement and retirement, which are all on this continuum." 

"Your one-year goal-setting for yourself in self-employment, or your business, will have certain objectives that will also be based on where you are in your career," she continues. As a freelancer your early goals might be about learning the skills needed for successful self-employment, like  how to use QuickBooks, or other tracking and time management tools, setting up savings plans and figuring out exactly what type of work you really want to attract. Dr. Newman thinks three to five year plans can be more focused on the big picture, like saving for a house or starting a family. "It's ok to have personal goals and business or employment goals interwoven when you do this."

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