Reframe Your Life: Rethinking Freelance Work, Side Hustles and the Gig Economy

Repeat after me: I deserve to be paid for my time and skills.

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It seems like it’s almost a daily occurrence that mass layoffs at huge corporations and small companies alike. Sometimes, it feels like layoff announcements are happening almost hourly, especially if you use Linkedin.  It’s pushing millions of people out of work and into the gig economy and the world of side hustles.

If you went to a pricey college, never heard anything mentioned about freelancing and the gig economy and somehow ended up doing just that, you are not alone. When I was in college over ten years ago, the term “freelance” was never mentioned, and that was when the concept was beginning to gain popularity. From what I understand, not much has changed. Millions of people are going to college, leaving with a bunch of student loans and forcing them into the gig economy. They are completely ill-equipped for it.

Though I’m not sure why colleges aren’t teaching us everything we need to know about the gig economy, I do have a few ideas. One of which is that colleges still view the gig economy as uncharted territory even though it doesn’t seem to be dying down soon. As of December 2022, 44 percent of Americans have a side hustle.  (I think many will agree the pandemic has played a huge role in that.) The second is that teaching college students about freelancing and the gig economy will affect the bottom line of college. Think about it. The more people who know you can sustain yourself from freelancing without a college degree, the less people go to college and the less money those colleges make. So I’m really starting to think it’s no mistake that these colleges aren’t teaching everything you need to know about the gig economy. Now that people are catching on to the idea of side hustles on their own, it’s unsurprising that colleges have seen lower admission rates in recent years.

photo of high rise building similiar to those in New York city
This is what college should have taught about freelance work, side hustles and gigs.

Since college didn’t teach me anything and I graduated college in the peak of the early 2000s recession, I was forced to teach myself everything I could about freelancing. Some were hard lessons that took longer to learn than others.  Others cost me a lot of money while a few were pleasant lessons that changed the game in my earning potential.  I have a feeling that many people will be learning some hard lessons now as the cost of living rises and a recession is supposedly looming.

No, I’m not an expert, but I’ve compiled a list of some of the most useful freelance tips along the way. I’m hoping they will help you navigate your life as a freelancer, side hustler or member of the gig economy.  And if you’re looking to get a bit more personalized assistance about starting out as a freelance writer, you can sign up for some coaching sessions with me here. Here’s everything You need to know about freelancing and the gig economy that they didn’t teach you in college.

1. Have a balance between passion projects and money-making projects

When most people think about side hustles or working gigs they normally think fond thoughts about being your own boss and only doing the work they enjoy, but sometimes it couldn’t be further from the truth. Things change very quickly once your side hustle goes from a fun way to make extra money to a necessity for living and paying bills. You end up picking up any job you find out of desperation and worrying about paying bills on time. And of course, that quickly turns to burnout and despising that freelance gig you once loved. Make sure burnout doesn’t happen by scheduling time for passion projects that truly bring you joy even if it doesn’t pay what you’d like. However, have a limit because some clients take advantage of you when they know something is your passion.

2. Know your number and don’t waiver from it

One of the hardest things about freelancing or working, in general, is knowing your worth. The going rate for your services will vary based on industry and experience regardless if you are a blogger, freelance writer, graphic designer, uber driver, babysitter, etc… However, it’s important to know exactly what value you bring to the clients as well as what your time is worth so you can determine a fair price for yourself. Once you establish that number, don’t ever accept work for less than that. Once you go below your chosen number, it becomes easy to make it a habit. And of course, that makes it harder to make a living or reach your financial goals.

3. Be aware of what the job is costing you

Sure, a client may be paying you $100, but it might not be worth it if it requires hours of research, lots of follow-up, and a long time actually doing the job. Or that $60 to deliver goods may sound great until you realize it’s a 45-minute drive in each direction costing a lot of money out of pocket including gas, toll, and wear on your car. Suddenly, that $60 doesn’t sound so great. Your time and effort are your most valuable assets so make sure you are taking all aspects of the gig into consideration before getting blinded by the money. And of course, some jobs just suck the life out of you. Even a job that is paying well may not be worth it if it’s costing you sound mental health. This post from the blog Making Sense of Cents has some great insight into this.

4. Track everything

And I mean even the things you don’t need for taxes. Unfortunately for messy people, self-employment means having to track everything for yourself. That means you need to keep a log of everything from invoices, supplies, pitches, income, miles driven, phone calls, etc. Yes, it’s a pain but it saves you from a lot of headaches once you do need to recall the information. In the past, I relied on Excel spreadsheets and Google Sheets to track those things. I’ve since moved on to Asana and Notion. And Toggl is useful for tracking time.  However, it’s still a work in progress. There are several planners and trackers like this one that can help. I’m also a fan of the reusable sticky notes created by MC Squares to help me organize my upcoming freelance assignments and tasks to complete.

5. Surround yourself with the people in that niche

Though it seems like everyone is doing it, the gig economy can be very lonely. To salvage your mental health and help with growth in your industry, it’s best you try to align yourself with people in your niche. Not near anyone who does what you do? Head to the internet. As a freelance writer, it’s not always easy to connect with others when the industry seems to center around NYC. However, following #writerscommunity, #freelancechat or  #lifestyleblogger hashtags on Twitter helps me keep up-to-date.

6. Join a union or support group

Even though freelancing, the gig economy and side hustles aren’t new, there’s still a lot of uncharted territory. That’s why it’s also great to join a union or support group for your industry to get advice and help you navigate the unknown. Some of them will even help with navigating contracts, receiving pay, and negotiating. I’m personally part of the National Writer’s Union.  The Freelancers Union also has amazing resources, workshops, and more that are generally free. If you can’t find one for your industry you can create one on meetup or at least follow blogs with tips. One of my favorites is

If you went to college and the words side hustle, gig economy or freelance was never mentioned, you need to read this. Click To Tweet

7. Talk openly about your rates

I know it’s considered to be in poor taste to discuss how much you make with others, but I’ve learned it’s one of the only ways to make sure you are earning your worth. The anonymity in salaries leaves too much power up to the clients who unfortunately take advantage of our silence. If we don’t discuss our rates, it’s almost impossible to know if you are being paid fairly or not. It’s one of the reasons why NY created a pay transparency law that requires all employers to list the salary in the job ad. So get in the habit of speaking openly about how much you make. Don’t think about it as a cause for embarrassment or another way to brag. Instead, think of it as a way to empower yourself and help others arm themselves with knowledge.

8. Collect testimonials

Whether or not you’ve created a website or have been asked for references, it’s good to ask for them at the conclusion of every project. It’s better to have them on hand now than to be scrambling to gather them last-minute when asked. Make it even easier for your potential clients to write a winning testimonial by creating a Google form with easy-to-answer questions about their experience with you. Though I haven’t used it myself, VideoAsk is routinely recommended as well.

9. Use mail trackers

Depending on who you ask, you’ll hear a lot of discouraging facts about using email trackers. However, I’m here to tell you that email trackers are my best friend and a huge help in my freelancing journey. Freelancing requires a lot of cold pitching to people you’ve never met before. And unfortunately, people just don’t answer emails anymore. Save yourself the headache and get an email tracker so you’re not constantly wondering if your message went into a black hole or was ignored. If my email trackers let me know that my email was never opened or the person opened it multiple times and never responded, I’ll usually send a follow-up. (This is extremely helpful when sending invoices) However, if the email was opened just once and I didn’t get a response I’ll most likely move on to the next prospect and not bother with a follow-up message. How you choose to determine whether it’s worth it to follow up is up to you, but having a mail tracker can definitely help in that decision.

10. Aim to acquire three stable and consistent clients at one time

The good thing about freelancing is that no job lasts forever so you’re rarely bored. On the flip side, the bad news is that no job lasts forever. Yet, the bills don’t stop coming. So to make sure you have some kind of “makeshift” stability when it comes to freelancing I suggest you have three stable clients at any given time. Having three steady clients helps ensure that money is always flowing towards you even if one decides to cut ties with you. While I usually aim to make sure the three stable clients I have are the highest paying, they are also sometimes the most dry and uninspiring clients. However, that isn’t always true for everyone. But if it is true for you, try to fill the rest of your time slots with more interesting and enjoyable clients.

The good thing about freelancing is that no job lasts forever so you're rarely bored. On the flip side, the bad news is that no job lasts forever. Click To Tweet

11. Aim to have some avenue of passive income or semi-passive income

Freelancing is extremely freeing because it gives you the freedom to work when you want to. But you can very easily find yourself becoming a slave to freedom. Because you technically don’t get “paid time off” like a traditional job, it’s possible you find that you are ALWAYS working. It’s not an ideal situation. Even if you aren’t creative like myself, it is mentally exhausting to have a career whose income is dependent on your consistent output. It essentially makes you a slave to freedom. That’s why it’s suggested you create a passive income stream to supplement your practice as a freelancer. It could be an ebook that brings in recurring sales, a stock that pays dividends or even a blog that utilizes affiliate links. Whatever it is, make sure it gives you a bit of mental reprieve from your usual side hustle tasks.

12. Learn the difference between freelance and working for no benefits

While it seems like side hustles have appeared out of nowhere, they’ve always existed. The gig economy is nothing new. It’s been around forever. It’s just that a lot of businesses are very sneaky with it. A lot of these businesses like to advertise for jobs that sound something like this, “freelance position available 40 hours a week onsite in our NYC office working under prominent managing editor. No benefits” Now, that isn’t a freelance job or a side hustle. That’s a business trying to trick you into working full-time under a supervisor without providing you any health insurance, vacation days or benefits at all. What’s worse is a lot of them will try to give you crappy pay which also doesn’t make up for the amount you’ll have to pay in taxes for this “freelance” position. Get acquainted with your state laws so you understand what is legal practice when it comes to working freelance positions. A freelance union may be able to help you out with this.

12. Include a PIA fee if necessary

Being a freelancer means choosing the gigs you pick up and the people you work, but that doesn’t mean you won’t get some draining, overly demanding and soul sucking projects sometimes. If you suspect that will happen, don’t be afraid to tack on a PIA (Pain in the Ass)  charge to your quote. Of course, you won’t tell the client that. However, as a freelancer who determines how much you make, you have every right to charge more to make difficult or draining projects worth your time. And if it’s an issue that you keep seeing, you can also amend any future contracts as needed or choose to simply cut ties with that PIA client.

13. Prepare for leaves of absence

Freelancing has a lot of perks. Unfortunately, having paid leaves of absence isn’t one of them. It’s a lesson I learned the hard way when I had my first son. When I had my second son, I prepared accordingly and was able to take the US “standard” of 6 weeks paid maternity leave. Being able to take a paid maternity leave as a freelancer is still one of my proudest accomplishments. It would be a good idea to stash a way a small portion of your paychecks for any leaves of absence even if you aren’t pregnant. You never know when sickness, death, etc will strike.

14. Master the art of the pitch

I don’t care if you don’t work in sales. Everyone needs to learn how to pitch. Whether you are a babysitter on, event planner or a freelance graphic designer on, you will need to use a pitch in emails, online profile, etc. As a freelance writer, I spent the majority of my early career writing and sending pitches to potential clients. (Once you master the pitch, you’ll rarely have to write them because repeat customers and referrals can keep you afloat. Unfortunately, it’s a skill I’ve found that colleges don’t typically mention despite it being necessary in almost every industry.

Do some research on how to develop a good pitch. Once you can write a killer pitch, your earning potential is endless. Though she focuses on freelance writing, the blog Make a Living Writing has great tips on writing pitches and letters of introduction for several industries.

15. Refrain from buying all the online courses

Yes, investing in courses can save you time but it can also end up wasting money if you don’t do your research. It seems like everyone wants to sell some online course without having proven results or their own success. Do your research to make sure the person practices what they preach instead of just repackaging information they read in a blog or some library book about business.

What am I missing? Are you a freelancer with a tip for those diving headfirst into the gig economy?

If after reading all of this, you’re still a little lost and want to learn more about freelance life, you can sign up for one of my free “freelance exploration calls” here. 

You can also sign up for some personalized advice with clear takeaways for your freelance writing growth for a one-hour coaching session here. 


TERRIfic Words: Don’t work for money. Work for freedom.

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  1. I somewhat freelance as an artist. This information is solid. I definitely see the freelance bubble getting larger especially on social media.

  2. So much awesomeness in this one post! You really said a word..especially about not getting caught up in enrolling in so many online courses. I have been telling folk that for years.

  3. 15 tips , good stuff! And informative, for example, I was not aware of bidding sites, but I am presently. I am not a solid freelancer, mostly I done a couple of big long-term projects related to marketing, not writing, although I enjoy blogging when time allows. Perhaps I will dive in deeper in the next year or so, meanwhile you listed some interesting sites that I’m looking forward to checking out, and I wish you much continued success with all your freelance endeavors.

  4. Thanks for the heads up! I’m going to keep this in mind because I haven’t ventured into the freelance world but it’s on my list of things to do soon.

  5. This is a great list, very informative and useful tips. I always struggle with pricing. I’m learning to charge my worth especially of others are making money why can’t I.Its super important to have a tribe of people in your circle that have the same niche, so you can help each other out

  6. These are excellent tips, that “Be aware of what the job is costing you” is huge. We are so used to doing things that we forget all the small things that it takes to pull of the big thing. I need to do better at getting testimonials. I’ve been slacking in that area.

  7. Just what I needed right now. This is a very useful and important piece of information. As a freelancer, it’s really important to kanaow your worth, so you don’t get cheated

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