Jun 12, 2020

Interview with Carolyn Bothwell, Founder of Freelance Founders

We chatted with Carolyn Bothwell, Founder of Freelance Founders, about best practices for new freelancers and the importance of building a community.


Whether freelancing is your full-time job or side hustle, there are so many things to consider (or re-consider!) when embarking on this journey. From learning how to market yourself, to writing your first contract, to chasing invoices, freelancing also offers up lots of growth opportunities, mistakes and rewards. While it’s empowering to take the leap, it’s even better when you have a strong community, or network of people, on your side. To explore this topic a bit more, we sat down with Carolyn Bothwell, Founder of Freelance Founders to understand some best practices on how to get started as freelancer and stay connected.

Kristen: What has been your experience as a freelancer, and what did you wish you knew before you made the leap?

Carolyn: My experience freelancing has been really rewarding. Yes, there’s been bumps in the road and tough clients, but overall, I’ve never looked back. Prior to making the leap to freelance life, I wish I had known how many other people actually do it! It took me a while to find a community of creatives that I could tap into for advice and friendship. If I had known there was such an incredible support system out there, I certainly would have made the leap even sooner.


What are key things freelancers should keep in mind to help them power through their day?

Find your peak productivity time! For me, it’s early in the morning, when I’m not distracted by Slack, email, and client calls. As freelancers, we’re so fortunate that we’re not tied to the 9-to-5 schedule, but we’re usually juggling a million things. So, personally, I’ve found it really helpful to block off time in my calendar to do my client work when I’m most creative. Then, I save my administrative tasks for later in the day. Invoicing always happens during my 3pm slump.

What sorts of apps and tools do freelancers use to help manage their businesses and stay on top of their work?

There’s a lot of great and affordable options out there to make your workday more organized and efficient. I love Asana for project management, Quickbooks for invoicing, and Squarespace for keeping my portfolio up-to-date. But, you have to find what works for you! I’m a writer – and I am terrible with numbers – so I hired a bookkeeper and started using Catch. Now things things are done by someone else or automatically. Highly recommend! 

What do you think freelancers typically miss the most about a traditional job, and what are some things they can do to make up for it?

While I can’t speak for everyone, I know that anecdotally, it seems we all miss having benefits. Whether that’s a healthcare plan or a 401k, benefits are some of the most difficult things to figure out as a solopreneur. (Hence why I’m so glad to have found Catch!) Personally, I’ve always found that the pros of freelancing far outweigh the cons. Most of the freelancers that I’ve spoken to have been able to recreate a steady and stable stream of income, and they’re able to do so while working on projects that align with their personal brand. Freelancing brings a lot more freedom and flexibility.


What can freelancers do to help them feel a part of a larger community? Why is this important?

Slide into people’s DMs. Join networking groups. Ask friends of friends to set you up on coffee dates. When I first started freelancing, I created an Instagram dedicated to my business, and direct messaged a lot of other freelancers and small studios on Instagram. Now that I’ve been freelancing for nearly three years, I understand how much I welcome hearing from other people in my creative community. I’m always looking for people to partner with when a project is beyond my skill set, and I enjoy connecting with freelancers that are also dealing with similar challenges that I am – quarterly taxes, MIA clients, etc. When you have a community, at least you can find the humor in it all together. It makes the day-to-day much more enjoyable.


What do communities and networks do for individuals and how do you see Freelance Founders bridging that gap?

Currently, there’s a lot of great communities and networks out there. I’m a member of the Wing, a co-working space, and I also participate in many of the Facebook groups, such as Freelancing Females, Dreamers & Doers, and Create & Cultivate. Communities and networks can help you crowdsource information and get the occasional gig. I recommend joining as many as you can. 

However, I felt like there was a gap in the market. So many of the current communities rely on crowdsourcing information, even when it comes to important business decisions. Freelance Founders is a community for creatives who are building freelance businesses for the long-term, so our membership model allows members to get access to experts in legal, accounting, and more. We’re also a closed community, so our members can actually reap the benefits of what we’re offering, without being overwhelmed by the number of participants.


How have you seen freelancers thrive in a community (whether it be an app, a social “club”, an organized Meetup?)

As freelancers, it’s easy to feel really siloed. Even when we’re collaborating with our clients closely, we’re still not a full member of their team. I’ve seen many freelancers thrive by tapping into communities. The wider your network, the more opportunities you will have. At this point, all of my clients are referrals from within my creative community. And, I’m hoping Freelance Founders can help cultivate that reciprocity for our members.

What are some things you want freelancers to keep in mind when work - or their days - get challenging?

It’s your business. If you’re having a tough day, week, or even month, think about what tasks are causing your challenges. If a client isn’t a good fit, you don’t have to continue working with them. If you hate invoicing, consider hiring help. When it gets challenging, remember that you have the freedom to change that in some way. That’s the beauty of being your own boss! 


Sign-up for Freelancer Founders here and Catch here.

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