questions to boost your freelance business
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Freelance Business Review: 5 Questions to Boost Your Freelance Mojo

Even though spring cleaning has always been a ritual of every lap around the sun, with the trend of the Marie Kondo method, it’s even more popular in 2019. Most people naturally glance at their closet to rid of items they haven’t worn in many seasons or to their kitchen, with plastic wear falling out of their cabinets. Some will tackle their junk drawer — or if you have the space — junk room. A tidy home might bring joy indeed — but maintaining a bustling, lucrative and successful freelance career definitely sparks glee.

Freelancers need to continually evolve

In addition to juggling various clients, staying on top of invoicing, managing your calendar and countless other responsibilities, remaining fresh is also part of the solopreneur gig. In a competitive marketplace that relies heavily on the freelance community, being on the top of your game means constantly evolving, adapting and pivoting.

“The 1099 workforce continues to gain momentum, controlling our success with the freedom to decide how, when and where is a liberating, non-traditional approach to working,” executive coach and author, Nancy Capistran explains. “However, as independent contractors, or freelancers, we need to continually evolve. We need to be intentional in our efforts to remain fresh. This means not getting stuck in a rut. Instead of being proactive and self-motivated to search out and learn new skills while continuing to grow our relationships, knowledge and experiences.”

If you’ve been in the pitch, write, submit and invoice dance for a few years, there’s a chance you could be falling behind on your professional development without realizing it. This is when it’s time to give yourself a hard — yet honest — review of your business, your day-to-day productivity, your process and your performance. Since no manager will hold you accountable, it’s up to you to set the bar higher. It won’t be easy, especially since Capistran notes most people are highly resistant to change. Being in charge of your own self-critique makes it that much more intense.

“Most people lack objectivity in assessing their own skills and abilities. No one is perfect. Being real and crystal clear with ourselves about the reality of our performance, on a regular basis, will expand our achievements,” Capistran continues. “It is just as important to know where you have gaps in your abilities, as it is to know where we are brilliant in our work. Career development is crucial for those that want to nurture their aspirations.”

So how do you begin the process of freshening up your freelance career? Start by asking yourself these questions, straight from career experts:

is my work challenging me

1. Is my work challenging me?

As every freelancer will tell you, some publications are more demanding than others. Some are more tedious with edits or demand faster turnarounds. Corporate blogs for brands can be time-consuming and a bit mind-numbing — but the paycheck is stellar.

Though some easy-and-out-the-door work is great to have, it’s also important you’re continuously challenged, career expert and CEO of Wethos, Rachel Renock stresses. “Consistently pushing yourself outside of your comfort zone can help you continue to get better, as an independent worker it can be easy to get a few consistent clients and get comfortable,” she explains. “Adaptability quotient is one of the most important traits that we’ve seen on our freelance teams, the ability to react quickly to changing environments, circumstances, or new information is one that can be strengthened by putting yourself into more situations where you’re focused on solving for a problem rather than delivering a solution.”

If you feel as if everything is currently status-quo, smooth-sailing and brainless, consider signing up for a course to expand your proficiencies. Or tackle a larger story or client you were intimidated of. When you push yourself with one client, you elevate your work with all.

2. What motivates and stresses me about my work?

For some, dealing with edits or implementing stories into a CMS. Others, finances. Whatever the perk and the pitfall, Capistran urges freelancers to get nitty-gritty about what motivates — and stresses them out. “It’s important to understand both your strengths and your areas of development. Being intentional about strategically improving your areas of deficiencies while also focusing your energy in areas you feel most inspired and fulfilled,” she explains. “This will drive your achievements forward.”

strong community to help raise the bar

3. Do I have a strong community who can help me continue to raise the bar?

Much like having a workout buddy or enlisting a friend to join you on your dream two-week trek through Europe, there’s strength found in numbers. And inspiration, since freelancing can sometimes be a lonely existence. Joining networks of fellow solopreneurs or writing communities not only provides a sounding board — digital or otherwise — but it teaches you valuable skills as others lead by example.

“Surrounding yourself with other people who are working with similar lifestyles but complementary skills to yours can be really useful as a freelancer who’s looking to grow and remain fresh,” Renock shares. “The better you can understand what you bring to the table when thinking about more complex initiatives the more thoughtful you can be in delivering to your client and your relationship will deepen.”

4. Is my routine and workspace allowing me to be productive and creative?

If your workspace is whatever corner of the couch your child hasn’t stained, or the comfort of your bed where you alternate between watching an episode of Netflix and then writing an article — consider this your reality check.

Entrepreneur, business writer and speaker Mandy Gilbert explains a bit of spring cleaning where you file away your stories, pitch ideas and answer emails can go a long way in developing your mindset. And it’ll keep you on track. “Procrastination is one of the hardest obstacles to overcome for freelancers. From doing the laundry to making a snack, your home is full of distractions. Without a proper home office setup, you could be pulled away from focusing on the task at hand,” she shares.

Considering it’s a valuable tax write-off, it’s worth looking into joining a co-working space if there’s one near you. Here, you have a built in network of other 1099ers, and you can upgrade to have a personal seat every time you stop in.

what does success look like to you

5. What does success look like to me?

To make money and never work for anyone ever again — right? Well, answer it for yourself.

Still thinking? The truth is many freelancers are terrified when they first leave the comfort of full-time employment and spend the first few years prepared for the bottom to come crashing out of their careers. For those who are successful and ride the ebbs and flow of work, it’s important to take a second, pause and consider your goals. If you don’t have quarterly, yearly and multi-year aspirations, you’ll feel as if you’re treading water, instead of enjoying the lifestyle you built for yourself.

“Without helping yourself define what this means, you can end up getting lost in the world of ‘hustle-porn.’ You become susceptible to burnout, constantly reaching for something intangible and feeling like you’re never improving because you have nothing to ground you in reality,” Renock explains. “It’s hard to celebrate a ‘win’ when you don’t know what a ‘win’ looks like, and therefore it’s hard to grow and remain fresh.”

So right now, while you’re munching on salad (or let’s be real, hummus and carrots because you had four deadlines today) — take a minute and define what success means to you. Let this guide your decisions — and help shape your progress.

Lindsay Tigar

About Lindsay

Lindsay Tigar is an experienced, established travel and lifestyle journalist, editor and content strategist. Since uprooting from Asheville, North Carolina in 2010 to Manhattan, Lindsay's work has appeared on several websites, including Travel + Leisure, Vogue, USA Today, Reader's Digest, Self, Refinery29 and countless others. While she is always up for the challenge of any assignment, her main areas of focus include travel, wellness, career, psychology, love and healthy living.

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