Six Tips for Freelancing Your Way to a Full-Time Gig

girl working on freelance marketing

When I graduated from Startup Institute Chicago, I had two problems that loomed over me in my job search:

  1. I didn’t know what type of marketer I wanted to be.
  2. I didn’t have a large portfolio of work.

Startup Institute gave me a great background in the different marketing functions; from email marketing, to content strategy, PPC campaigns and social media. I even had the opportunity to work with two different partner companies and add that work to my resume and portfolio. However when I graduated, I realized that I had enjoyed most functions equally and as a career switcher, after just eight weeks of marketing immersives, I didn’t have a large body of work to show for my abilities.

Then I discovered the beauty that is freelance marketing.

Freelancing, or doing part-time contract work for multiple clients, is the perfect way to not only get experience and build your business portfolio but– more importantly– to give you a taste of the different types of opportunities in your field. Contract work is a fantastic way to figure out what you want to do and what type of company you would like to join (check out oDesk and Elance for help finding freelance work).Freelancing is a great way to get experience and build your portfolio says @care_oh_liine Click To Tweet

However, if you’re someone like me who has always had a structured, full-time gig, freelance marketing has it’s own set of unique challenges. It requires a totally different mindset and skill set. Here are some of the lessons I learned the hard way from my time as a contractor in the Chicago startup scene:

Freelancers have to stay organized.

Managing multiple clients with multiple needs on multiple deadlines was far more challenging than I had imagined. At one point, I had up to four clients who were using different email platforms and vendors, plus had different content needs, writing styles and Google Adwords accounts. It got overwhelming. Be sure to utilize a project management tool to keep yourself organized. Whether it’s Google Tasks, Asana, Trello, or others, there are many free project management software options availableUse @asana to keep #freelance work on track, says @care_oh_liine Click To Tweet

Don’t be afraid to talk about money.

Money matters! As a new freelancer with limited experience, I struggled with understanding how much to charge clients. Though it may be intimidating for many beginners, this is a necessary part of the game.

Unsure of how much to charge? Do some research. There are various online resources (such as this freelance rate calculator), but be mindful that company-size and your professional experience will yield different rates. Network with other freelance marketing professionals to get an idea of the market rate. I reached out to a fellow student who had been freelancing on the side for over five years and she gave me a ballpark range. Every organization is different. Some will prefer to pay an hourly rate. Some may prefer to get an estimation of the cost of the content piece upfront– charging by blog post or eBook. What’s important is that the terms are very clear upfront.

Which brings me to my next point…

Always get a business contract in writing.

The startup community in Chicago is very welcoming, open and friendly. My first jobs in freelance marketing were obtained from introductions to instructors at Startup Institute, or from acquaintances at networking events. As a naturally trusting person, I tended not to put too much in the written business contract and put more in the verbal agreements.

But I learned the hard way that even that founder-friend-of-a-friend may not have the best intentions. And, even if they do, young companies can sometimes be… let’s just say… not the most organized. For these reasons, it is crucial that you have a clear, written business contract that is agreed upon and signed by both parties. No exceptions. Check out this free contract template for some ideas on how to create your own. Although most of these contracts are quite simple, if you have a lawyer as a friend, now is the time to call in that favor and have them glance over the contract.Create clear, written contracts for #freelance jobs. No exceptions, says @care_oh_liine Click To Tweet

Although the high majority of my experiences were positive, I wasn’t alone in having contract woes. Remember that this is still business and having concise paperwork benefits all parties.

Don’t be afraid to show off.

Starting as a freelancer, I realized that I had a lot more relevant experience than I had given myself credit for. During my two years as a Peace Corps Volunteer, I had run successful crowd-funding campaigns on two different platforms, written blog posts, managed social media accounts, and acquired a lot of project management experience. Freelance marketing opened my eyes to the types of skills that I had to offer and helped me tie together my previous experiences.

Freelancing is all about being able to demonstrate your work, so don’t be afraid to show it off on multiple platforms. A resume is the old standby, but be sure to have your work and contact information displayed on your own personal website. There are so many free options out there today (here are some that don’t include foreign advertising). Although it seems like an obvious tip, you would be surprised at how many people (especially marketers) don’t have their own websites. Additionally, LinkedIn now has great features, such as a “Projects” heading where you can list specific pieces of work and even link with different collaborators and companies. If you’re unsure on where to start, take a look at this list of advice on how to make a portfolio.Don't be afraid to show off what you can do on different platforms says @care_oh_liine Click To Tweet

Small companies aren’t for everyone. Neither are big ones.

When I graduated Startup Institute, I had the nagging feeling that I wanted to be at a larger growth-stage company or scaleup, and on a marketing team. Many of my peers, however, had their sights set on small, early-stage companies where they could come in as either the sole marketer or lead a very small team. Despite what my gut was telling me, I found myself drifting towards small companies and taking on full-stack freelance marketing roles. And it was not for me.

That’s the beauty, again, of freelance work; you get to experience a taste of what it’s like to take on different types of roles in different sized companies. Although I learned a great deal from being the sole marketer in one of my larger contract positions, I also learned that I was not yet ready to take on that role as a full-time position. It helped me steer my job search in the right direction and landed me at Signal, where I now happily serve on a marketing team of ten. Freelance for different types of companies and then trust your gut.Follow your gut. If you're not sure, #freelance to explore work options @care_oh_liine Click To Tweet

Say yes!

When I got my first contract offer, I was terrified. Sure, I knew I was a good writer. And sure, I had run email campaigns for our partner project during Startup Institute. But to take on the management of the marketing program for an entire startup – it was intimidating. I almost turned it down as my confidence faltered and I began to doubt myself.

But, after a meaningful talk with the staff at Startup Institute, I realized that I had all the tools at my fingertips. “What’s the very worst that will happen? They’ll end the contract.” So I accepted and dove right in.

I’m not saying that you should sign up for things that you honestly do not feel equipped to do. What I am saying is that you should believe in yourself and give yourself the chance to perform. The best thing about being a Startup Institute alum was that I had the support and backing of the community. The personal recommendations and introductions I got from the staff helped me obtain my first clients and built my confidence. I never felt alone; I always knew I had fellow alumni and instructors to ask questions and receive guidance whenever I struggled.Believe in yourself and give yourself a chance to perform says @care_oh_liine Click To Tweet

Freelance marketing was never my long-term goal, but without it, I wouldn’t have been able to narrow in on where I wanted to work and what I wanted to do. So whether you’re a current student, or recently graduated, don’t turn down the opportunity to pick up contract work and let it steer you in the right direction.

Photo credit: Startup Stock Photos

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Caroline is graduate of the SI Chicago Fall '13 class in technical marketing. A life-long adventurist, she found her home in the Chicago tech community after returning from the Peace Corps in 2013 and is currently Marketing Manager at Signal. When she's not plotting her next adventure, you can find her writing at her blog or singing Beyonce in the shower.


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