6 Freelance Lessons Learned from The Successfully Self-Employed

freelance lessonsThis past Saturday, I learned a lot of freelance lessons at Hustle Fest, a ‘summit for the self-employed’ hosted by New Women Space (NWS) and Jillian Richardson, a freelance writer and emerging event producer.

Hustle Fest brought together a community of freelancers, consultants, and solopreneurs to learn about and discuss work/life balance, building community, authentic networking, and business practices.

The day was absolutely bursting with information and insight, but here are my top six freelance lessons learned:

1. Develop a Sales Mentality

I didn’t study sales or marketing, and the first keynote speaker, Chris Gillespie, made me remember that. Chris is a former salesperson and the CEO of Find A Way Media.

Chris recommends developing a sales system—as opposed to committing ‘random acts of sales.’ In other words, creating a sales funnel that works for you and your specific needs and goals.

The way Chris sees it, freelancing has four parts: product, marketing, sales, and service. Most freelancers spend the bulk of their time honing their product and end up neglecting the rest. But product is only one part of the many interconnected pieces that make up a business.

Chris suggests freelancers and business owners spend some time identifying, assessing, and working on the parts they have neglected. This way, we can begin driving more leads into our sales funnel. Chris goes into depth about this in his e-book, Freelancer Sales Strategy.

2. Create a ‘Third Space’

I struggle a lot with creating a work-life balance—and I know I’m not alone. Ironically, part of me knows what I should be doing to live a more balanced life. Yet, in my mind, it can feel like I just don’t have the time to put these wellness habits into practice. Oh, the irony.

Rachael Ellison, an Executive Coach specializing in Work-Life Synergy, spoke about the freelance lessons like creating a ‘Third Space.’ For some of us, our work-focused selves and life-focused selves exist in two different spaces and transitioning between the two can be hard. For this reason, Rachael recommends developing transitional practices between these two spaces.

A ‘Third Space’ serves as a period of mental transition between work and home. Rachael recommends creating specific transition rituals, such as changing music, changing clothes, or taking a walk. By utilizing these ritual practices and creating a buffer zone, we can allow ourselves to transition more smoothly and healthily between our work selves and our—well— self-selves.

3. Identify Your Limiting Belief(s)

One of my favorite parts was Jillian and Melissa of NWS sharing limited beliefs they have had about themselves. Whether it’s insecurities about personality type, talent, or ability, the reality is: all of us have limiting beliefs about ourselves that get in the way of us reaching our full potential.

One of the most important freelance lessons we can learn for ourselves and our careers is to take time to identify what these beliefs are, so we can catch ourselves when we’re succumbing to self-doubt.

As an artist and creative, I still struggle with believing in myself. This can affect my ability to ask for what I deserve in the professional world. Speaking with fellow Hustle Fest-goers, I know I am not the only one with these issues. All of us struggle with insecurities or dreaded ‘imposter syndrome’ that tricks us into thinking we are somehow not enough.

So, next time you are nervous about meeting with a new client or find yourself in a spiral of negative self-talk, take a moment to think about the internal narratives you tell yourself about your limits—chances are, they aren’t even true.

4. Know Your Worth

Figuring out your worth is a huge struggle for freelancers, particularly for women and marginalized people. This is why Hillary Black of Kay & Black Talent Management recommends getting real with yourself.

“What’re you willing to get out of bed for?” Hillary asked. Though it’s tempting to jump on any offer—especially as a fledgling freelancer—Hillary recommends setting mental hourly, day, and project rates that you won’t dip below. (However, she also recommends being flexible with yourself; if business is slow, you might have to dip below these guides. But make sure to develop criteria to figure out if and when you can make exceptions.)

Another of her freelance lessons is to develop a squad of friends, colleagues, and hopefully even an ex-client or boss who you can consult about rates while helping you to craft one that makes sense for you.

Beyond this, Hillary recommends figuring out what you need to feel good and what you need to feel great.

As you move forward with your business, frame Y as your starting point—”I make upwards of Y, but I’m open to hearing your thoughts”—that way if they negotiate you down, you’ll still be in a great place.

5. Create Your Signature Story

The day’s second Keynote speaker was Steve Roller, founder of Copywriter Café. Steve spoke at length about how to stand out in the freelance economy and—bottom line—it isn’t always easy.

However, out of the several things Steve recommended, one stuck out the most: taking the time to craft your own ‘signature story,’ an expanded elevator pitch that explains who you are, why you do what you do, the type of people you work with (and won’t work with), and why you are different (and better).

Steve’s freelance lessons include being as transparent as possible about your so that clients know and understand how you work.

Start by writing out a document that outlines all of these things in depth, then use it as a guide for client negotiations and business development. “Clients have a hard time sorting through all the noise,” Steve said. A well-crafted signature story is a way to connect and build trust with your clients.

6. Remember: You Aren’t Alone

After spending the day surrounded by a diverse room of people of different races, genders, careers, and crafts, I left with a wealth of information, a renewed sense of purpose and determination.

I also left with notion welcomed by any lone wolf creative: that, perhaps, I’m not alone after all.

Events like this serve as a crucially important reminder that we’re not in this by ourselves; there are countless people out there who have faced the same struggles as you—from client non-payment to imposter syndrome. It’s important to keep this in mind as you find your footing.

Though networking is important in any career. Taking the time to invest in real relationships and community can make all the difference.

In fact, it might be one of the most worthwhile freelance lessons you can learn.


For this post, we’d like to thank our friends at Levo.





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