Tips for Surviving & Thriving in the Gig Economy

It’s all fun and games until someone owes you $30,000.

My MacBook is as well traveled as I am.

Two and a half years ago I quit my job as a newspaper reporter and started freelancing.

About a year ago, I shifted to introducing myself as the owner of a copywriting agency, because legally, there’s no difference between the two, and you get a lot more respect from the second introduction.

That’s just one of the lessons I’ve learned in the last 31-ish months of freedom.

I have also learned that it’s not exactly freedom either. I exchanged a job I could leave at the office every evening, every weekend, and 19 working days per year, for a job that follows me to remote Vietnamese islands, world-class climbing destinations in Mexico, primitive campsites in South Dakota, and the tops of mountains in Wyoming.

Now, my biggest struggles are finding a balance between being accessible and dedicated to my clients and having a life, and saying no to good opportunities that come up at bad times. I recognize that these are good problems to have.

I recently shared some of my experiences as a business owner at a panel in Madison put on by Women in Tech, and it inspired me to share some of the insights I’ve gained about surviving and thriving in the gig economy. I share these with the caveat that I am still learning how to put all of these tips into practice, and I’m still making mistakes every day (especially when it comes to saying no).

Before I dive into the tips, let me start with two disclaimers:

ONE: I’m going to assume that you have a marketable skill (it doesn’t have to be writing, just look at the awesome variety of professions we get at the Madison Freelancers meetup) and you have a reason to believe you are skilled enough to make it on your own. The things that made me believe this were the four years of experience writing professionally and thousands of published articles I gained in my first two jobs out of college. It will be different for you.

TWO: I cannot overstate the importance of having a decent amount of savings. I recognize that it is a privilege to be able to save money. It’s a privilege that I took advantage of, which allowed me to quit my job and start experimenting with a minimal amount of stress, knowing I had enough to last me at least six months if I earned nothing from freelancing (I also sold my car and moved in with my girlfriend to cut my expenses).

How to Get Started in the Gig Economy

Don’t let a website become a barrier

Branding is an awesome tool in marketing. A sleek website, a cool logo, a memorable business card — these are all things that can take your business to the next level, if they have the right business strategy behind them.

But here’s the thing: creating that business strategy is really tough when you’re first starting out. You can’t just pick a niche out of thin air. You don’t really know what your value proposition is because you haven’t worked with any real-life clients yet. So the chances of you nailing the branding on your first try are slim.

I’ve experienced this and watched many of my fellow business owners struggle with this: when you’re first starting out, you don’t know what your brand is supposed to be. You spend hours reading Start With Why and other similar books, and you’re hell-bent on building the perfect foundation for your business. You don’t want to build a website until you know EXACTLY what it needs to say, and you’re not ready to put yourself out there as a business owner until you have that awesome website.

My advice, learned the hard way? Don’t worry about the website or the logo until at least Year 2 of making a profit. All you really need is a basic portfolio site. This could live on your LinkedIn profile (a simple headline, summary, and three links to your published writing), on a super basic website like my friend Rachel’s, or a portfolio platform like Contently.

Keep it super simple, and change it as often as you need to, testing out each version on your new and prospective clients.

Pick a product niche, not an industry niche

Apart from a handful of industry-specific words and concepts that you can probably master in a day’s Googling, ALL INDUSTRIES ARE THE SAME. You’ll get clients asking if you have any experience in the construction industry, or the manufacturing industry, or the legal industry, or real estate. And while it’s certainly a plus if you do have that experience, at the end of the day, if you present the image of a highly competent professional who brings an established process to your work, then the customer will realize you are certainly capable of getting up to speed on a new industry.

So how do you make sure you always present that professional image? For me, the key has been to focus on a few kinds of products. As a copywriter, I call deliverables like “White Papers” or “Pitch Decks” or “Blog Posts” products. I prefer that over the word services, because “writing” can touch literally every aspect of a business, and if you’re not careful, you can end up offering ALL KINDS of writing “services” that make it impossible for you to define one established, repeatable, measurable process.

Here are some products I see a lot of demand for:

  • White papers (An in-depth article, typically 10+ pages, telling a company’s story, or answering clients’ most complex questions, in an in-depth format. A client might want to introduce the world to their business model, or present research results, or introduce a new product or service.)
  • Case studies (A case study is an in-depth client testimonial created to help attract more of your client’s ideal customers.)
  • Pitch decks (The Powerpoint presentation a startup would use to convince investors to give them money. Slides should communicate clearly even without the speaker, but should also be simple enough that the speaker can use them during a presentation.)
  • Weekly or monthly blog posts, with a newsletter to distribute them
  • Website copy (WARNING: Writing website copy is a dangerous, slippery beast. I have officially decided that it is not a good fit for my agency, and I will no longer be accepting this kind of work unless I have a long-held working relationship with the client and I know that I can produce what they are looking for. But literally everyone wants to hire you to write their website. Proceed with caution.)

How to get clients

Let your curiosity be your guide

I’m an extrovert (although sometimes I ring up as an ambivert), so my tips will skew towards more direct interaction with strangers. There are other ways to get clients, so if you have social anxiety and these tips are useless to you, look for other tips written by introverts. They are out there! Do not be discouraged!

Even though I live for human interaction, I still hate the idea of going to a business networking event where everyone is trying to get new clients, and I just need to work the crowd. So instead, I attempt to remember to carry business cards with me everywhere (I mostly forget), and I just go to events that spark my curiosity at all times of day, on all kinds of subjects. And when I’m there, I talk to people. I like to find out why other people are interested in the topics of the event (whether it’s sustainability, or racial justice, or science writing, or rock climbing, or running, or emerging technology, or whatever).

In the course of our conversation, if they ask me what I do, I either say that I’m a copywriter or that I own a copywriting agency (remember the intro of this post? I DON’T say I’m a freelancer.) Often, this leads to the follow-up question: “Oh, what kind of stuff do you write?” And then I recite my elevator pitch: “I write marketing copy — like blog posts, white papers and email marketing campaigns — for a variety of organizations, and currently I’m doing a lot of work for cryptocurrency startups.” Frequently this leads to an email introduction to a friend or colleague who is in need of a copywriter.

Write and publish often

One of the keys to my early success was my LinkedIn page (it is dusty and covered in cobwebs now but you can look if you like). Back in 2016, I had an awesome platform on LinkedIn because when I hit “publish” on a blog post, almost 10,000 people got a notification, and often, thousands more saw my post in their LinkedIn news feed, thanks to a lot of support from LinkedIn’s editorial team at the time. I wish I’d been smart enough and coordinated enough to really use this platform to its full advantage. But I published a lot of rants about marketing and “insights” about freelancing, and I got a lot of attention. For many people, my writing was proof that I could write well, and that I had strong opinions that I wasn’t afraid to share. Many people are attracted to that, and decided to hire me because of it.

Your platform doesn’t have to be LinkedIn (in fact, it’s not a great place to publish longform content anymore). Maybe it’s YouTube, Instagram, Medium, or a small email list made up of your friends and family. Or maybe you can find a local magazine that’s hurting for contributors and strike up a relationship (they’re unlikely to pay you, but this is one case where exposure can help you eventually pay the bills).

Here are two copywriters on LinkedIn who use the platform very effectively to draw attention to their ability to write, and then start conversations that lead to a lot of great gigs.

Sara Rosinsky

Laura Riley

Volunteer strategically

Don’t give away your work for free, UNLESS you have a good reason. There are several good reasons.

One, maybe you haven’t figured out your processes around creating a certain kind of product (or providing a specific service, but again, I like to think of it as a product). If you get an opportunity to test out those products on a nonprofit client who can’t afford to pay you, and you believe in their cause, then don’t be afraid to try it out. I perfected one of my products over the course of six months working for a nonprofit as a volunteer, and when my workload got so busy that I couldn’t continue to offer that service for free, the nonprofit stepped up and agreed to pay me.

Two, maybe you are really passionate about a particular community or cause, and you can see how much they could use one of your products/services, but they’ll never be able to pay you. But if creating that product or providing that service for that community will give you a lot of chances to interact one-on-one with influential members of that community or leaders in that cause, then you never know where those interactions will take you in the future. I wrote a series of blog posts telling the stories of various members at my coworking space, and it has turned into several leads or paid gigs when those community members came back and asked me to work for them or connected me to a potential client.

How to stay sane from the first interaction to the final invoice

Know your minimum price

The best thing you can do for yourself as a freelancer or agency owner or whatever you call yourself, is to decide what is the minimum price you’re willing to work for. Without a minimum, you will spend hours staring at your screen wondering which number to pull out of thin air for this proposal. Seriously. And then hours doubting yourself after you press send. And then, potentially, days or months wishing you had said a different (higher) number after the client accepts your proposal.

Avoid all of this pain by deciding on your minimum price, and then sticking to it. If people can’t afford you, be ready to send them a list of other contractors in your area that they could reach out to.

My friend Laura lists her minimum prices directly on her website. I think that’s awesome.

Don’t do any work until you get 50% up front

This is the rule I break the most often, and regret breaking the most often. There is really no excuse for a client not paying you 50% (non-refundable) up front. And it changes the whole relationship. With 50% of the money in hand, you’ll be super motivated to do an awesome job, and you won’t be worried that the client will flake out and stiff you. They could still stiff you 50%, but you’ll likely get wind that that’s going to happen halfway through, so you’ll be able to sever the relationship without losing much. Also, your clients are WAY less likely to try to back out or flake out if they’ve already paid 50%. They’ll be more attentive, and more motivated to get you what you need to succeed.

Also, you should consider putting some careful language in your contract about how and when the final 50% is due, or what happens to the work you create if the final 50% never gets paid (i.e., you don’t give up the rights to the work, or you don’t hand over the password to the website, or whatever).

Set limits on the number of revisions and the timeline for revisions

I’ve gotten into trouble a lot for not making this clear up front. If you don’t specify how many revisions you include in your fee, and what the appropriate timeline is for a client to ask for those revisions, your client simply won’t know what to expect. They might ask for fewer revisions than they truly wanted because they’re being polite, but then they’ll end up disappointed with your work, or they’ll ask for a million revisions because you didn’t make your boundaries clear, and then you’ll be super frustrated with them.

Here’s my current policy:

“I will provide up to three revisions on each piece within the first 30 days after submission of the draft.”

Simple, but effective.

Seek out community

Whew — I didn’t really set out to write 2,500 words on this subject, but there you go. Working in the gig economy can be a great experience, or a terrible experience, or both at the same time. You can save yourself from a lot of heartaches if you apply some of the tips I’ve outlined here. And, when you inevitably break these rules, it helps to have a community of other gig-economy types to vent your frustrations and air your grievances to. There are dozens of online communities (just search Facebook), and hopefully your city has a thriving coworking space like 100state in Madison, or a Freelancer meetup like ours. If not, do like Matt Nelson did here in Madison and start one yourself!

Feel free to email me with questions. I love to talk about this and do what I can to help others get started because, for all of its new stresses and challenges, working in the gig economy has been an overwhelmingly positive change in my life.