5 Ways to Get Over Freelance Impostor Syndrome

5 Ways to Get Over Freelance Impostor Syndrome

Every decision can feel like a make-or-break moment as a solopreneur. You’re wearing multiple hats, making tough calls, and constantly stepping into uncharted territory. It’s no wonder so many of us struggle with anxiety and self-doubt.

You’re probably familiar with the concept of impostor syndrome. It’s the feeling that you don’t truly belong or deserve the success you’ve achieved — that you’re actually just fooling everyone into believing you’re legit. Most people experience it at some point or another. And for some, it can be a tough hurdle to overcome. When the fear creeps in, it can stop you from taking confident steps that might grow your business, like pitching a client, promoting your work, and asking for the rate you deserve.

Fortunately, impostor syndrome is so common, there are lots of proven strategies to combat it. Below, we’ll share our top five favorites.

How to Kick Impostor Syndrome to the Curb

Focus on the Facts

Impostor syndrome thrives in ambiguity — the foggy place between perception and reality, where we can take a neutral observation (like “they haven’t replied to my email”) and turn it into a damning narrative (“they think my work is terrible and my rate is too high”). The stories you weave when you’re anxious are usually rooted in scarcity and unworthiness. Recognizing that they’re not facts, but rather distorted self-perceptions, can be a helpful way to prevent a spiral.

The truth is, unless you’re a literal con artist or part of a royal family, you didn’t stumble into your success by chance. You’ve most likely worked hard, developed valuable skills, and overcome countless challenges to get where you are today. But when we’re facing impostor syndrome, we tend to minimize and overshadow our accomplishments. The way to stop that? By focusing on your accomplishments instead. Keep an actual track record of what you’ve achieved. Save the positive feedback you receive from clients and refer back to it. Note all the ways you’ve grown your business. By focusing on the facts, we can kick the illusion that we’ve faked our way to where we are, and embrace our strengths and accomplishments.

Connect with Members of Your Community

We all need people to mirror our gifts back at us sometimes, or just remind us we’re not alone. Strong, supportive peer relationships can be incredibly grounding, especially when you typically work solo. Freelancers don’t get annual reviews or everyday affirmations from colleagues and managers. So connecting with your freelance community can be a powerful way to counteract the nagging feelings of impostor syndrome that thrive in the echo chamber of your mind. Chatting about your struggles will often remind you how common they are, which can take the power out of the impostor monster too. Plus, you gain a sense of belonging, and who doesn’t want that?

Whether it’s through networking events, freelancer associations, or online spaces, building relationships with your community is worth the effort. You’ll likely discover that many of the people you admire have moved through the same fears and insecurities at some point in their journey.

Learn How to Quiet Your Mind

There’s a reason Buddhist teachings frequently refer to the “monkey mind” — the frazzled, distracted, anxious state so many of us are accustomed to living in. It’s the source of so much of our modern suffering. But there are ample (free!) tools that can help you quiet your mind, soothe your nerves, and counteract your inner critic. Mindfulness practices like meditation, body scans, and deep breathing can help, and so can basic actions like going for a walk or listening to uplifting music.

Anxiety tends to take hold when we get stuck in the past or the future instead of being present. So learning what helps you stay in the now — and building up your toolkit of coping strategies for when you get lost — is an absolute game-changer. It will benefit you in all areas of life. Quieting your mind is not about denying your doubts or invalidating your feelings. It’s the practice of acknowledging the fear and insecurity that’s rising up within you, while refusing to let it define you.

Celebrate Your Wins

As a small business owner, it’s easy to downplay your achievements, attributing them to luck or external factors rather than your own skills and efforts. And without colleagues bearing witness to your everyday wins, it can be easy to overlook them. But regularly acknowledging and celebrating your successes is essential for solopreneurs. It not only motivates you to keep going, but it can act as a powerful confidence-booster, reinforcing a positive self-image. So treat yourself to a coffee after you send that email. Share your wins with your community. Honor your milestones, big and small. And do it on a regular basis. These celebrations become affirmations of your power. And over time, they outweigh the false belief that you’re not enough.

Accept It

Instead of resisting or denying your feelings of self-doubt, try acknowledging their existence. It can be incredibly relieving to turn around and face your fear instead of running from it. Like the monster in your closet that turned out to be a coat, impostor syndrome is built on misperceptions — but we can’t see that until we turn on the light and look. The second you pause and get present with your insecurity, you begin to take away its power. And recognizing that impostor syndrome is a common experience shared by so many helps to normalize it too.

Self-doubt is a natural part of being a solopreneur, especially when we constantly push ourselves beyond our comfort zone. But acceptance opens the door to self-compassion. And the more you practice it, the easier it’ll be to find your footing again when impostor syndrome comes knocking. The goal isn’t to make it go away forever. It’s to get more skilled at counteracting it when it does show up.

Remember, you are not alone! I don’t know a single business owner who hasn’t struggled with self-worth, doubted their abilities, or diminished their experience. Impostor syndrome is a widespread struggle that so many face. And, ironically, it’s often successful, brilliant people who deal with it the most. So, know you’re in good company. But you don’t have to stay there. You’re deserving of your success, and all the magic that comes from seeing yourself as you truly are — a talented, worthy, creative powerhouse who’s only getting stronger with time.

7 Conferences for Freelancers to Attend

7 Conferences for Freelancers to Attend

Attending conferences can be a great way to stay up-to-date on industry trends and connect with potential clients and other solopreneurs in your industry. No matter what type of freelancer you are, there’s a conference out there for you. 

Here’s a list of 7 in-person and virtual conferences that should be on your radar if further developing your skillset and growing your network is a focus for you.

Best Conferences for Freelancers

General Conferences

Creator Economy Expo: This in-person conference is the go-to event for content creators of every type – including coaches and freelancers. Creator Economy Expo was organized for those interested in building and growing their content businesses without relying on social platforms. During this conference, you’ll learn from 40+ creators on how to build and grow your content business.

ConvertKit Conference: Created for creators, by creators, this 3-day conference is chock full of keynote speakers, workshops, creator meet-ups, and more. If growing your business and building relationships with other creators is on your to-do list, this conference is a must-attend. From leveling up financially, using AI to assist in content creation, niching down, and more – this conference covers all the basics and then some. 

Marketing and Social Media Conferences

State of Social: Crafted for those who work in social media, this annual conference dives into the current and future trends in both social media and digital marketing. If you’re looking to connect with other social media strategists, find inspiration, and learn from thought leaders in the space, this conference is for you. From keynote speakers to workshops covering everything from organic social to audio branding – this is a must-attend conference for all who touch the ever-changing world of social media. 

Digital Summit: Digital Summit is the nation’s largest conference series for digital marketers and has multiple yearly events taking place in cities across the United States. These events feature industry leaders discussing all aspects of digital marketing – from SEO to branding and everything in between. With former keynote speakers including Gary Vaynerchuk, Mark Cubin, and other thought leaders from leading global brands like Google and Microsoft, you’ll not only walk away from this conference with a deeper understanding of all things digital marketing, but with a cup full of inspiration.

DigiMarCon: DigiMarCon (Digital Marketing Conference) is the world’s largest marketing, media, and advertising conference and exhibition series hosting 40+ events annually in cities across the globe. Network with thought leaders, gain insight into the latest innovative technology, and hear from some of the most thought-provoking speakers in the industry on topics ranging from emerging digital strategies to the latest tech innovations. This conference will leave you feeling inspired and challenged.

Writing and Journalism Conferences

Chicago Spring Fling Writer’s Conference: From webinars to keynote speeches, networking, a silent auction, a book signing event, gala ball, and more, this romance writing-focused conference is perfect for both published and unpublished writers looking to network and level up professionally. The conference’s masterclasses cover timely and culturally relevant topics like Ted Lasso as Romance, and The War of Art – to name a few!

ASJA: ASJA (American Society of Journalists and Authors) is an annual virtual conference featuring keynote speakers and expert sessions led by some of the United State’s most successful freelance writers. This conference is perfect for those of you who want to connect with other freelance writers, gain confidence in your craft, and get inspired to take your career to the next level. With keynote speakers and workshops covering topics like 9-5 freelancing and making six figures as a freelancer, this is a conference all of you freelance writers won’t want to miss.

15 Freelance Newsletters to Subscribe To

15 Freelance Newsletters to Subscribe To

Want to stay ahead of the curve in the world of freelancing? Whether you’re new to the game or looking to take your freelance career to the next level, subscribing to industry newsletters is a great way to find the tools, inspiration, and insider tips you need to succeed.

Here’s a compilation of the best freelance newsletters to help you stay up-to-date on the latest trends, tips, and strategies.

The Top 15 Freelance Newsletters

The Writer’s Job Newsletter scours the internet to bring you the best freelance writing opportunities, delivered straight to your inbox every week. Whether you’re a seasoned pro or just starting out, this newsletter helps you stay on top of the latest writing gigs.

Content Connect by Ashley R. Cummings delivers valuable tips, strategies, and expert advice to help you improve your writing skills and grow your career. This weekly newsletter is packed with actionable tips, case studies, and examples to help you create more engaging and effective content.

Kaleigh Moore’s Weekly Newsletter is a free bi-weekly newsletter for writers. Each edition is filled with valuable tips and resources to help you improve your writing process, find new work, and cultivate new ideas. This newsletter covers a wide range of topics, from crafting compelling pieces to pitching to editors and more.

Freelance Bold by Marijana Kay is for you if you want to earn more by working with better clients, plan your freelance writing projects with boundaries (and without burnout), and get organized with strong processes. It’s delivered to inboxes weekly.

Peak Freelance’s Newsletter is designed specifically for writers looking to work with bigger and better clients, build a personal brand, and increase their rates. The weekly newsletter features the best freelance writing opportunities, along with tips and strategies to help you improve your writing skills, build your portfolio, and scale your business.

The Word by Dave Harland is a weekly marketing and copywriting newsletter that hits inboxes every Friday. Each edition is packed with valuable tips, techniques, and real-life stories to help you improve your marketing and copywriting skills.

Harlow’s Newsletter is a monthly newsletter that tackles the topics that matter most to the freelance community. From planning for an upcoming recession to navigating the ups and downs of freelance life to compilations of resources created to help you grow your business — we’ve got you covered.

Soloist Sundays by Winning Solo provides subscribers with valuable content and actionable insights that will help you thrive as a freelancer. And the best part? Each edition, delivered to inboxes twice a month, can be read from top to bottom in just five minutes.

Kat Boogaard’s Newsletter delivers freelancing tips, helpful advice, and freelance gigs straight to your inbox on a weekly basis. As a bonus, you’ll also receive Kat’s top ten tips for getting started as a freelancer directly after subscribing.

Kaitlyn Arford’s Newsletter is great for freelancers on the hunt for new clients. With 100 freelance opportunities delivered directly to your inbox every Friday, you’re guaranteed to find your dream gig.

Dear Freelancer by Brooklin Nash is a brand new newsletter chock-full of answers to top freelancing questions. You’ll get insight on Brooklin’s personal experiences as a freelancing pro, and more. If you want to learn from the best, we couldn’t recommend this newsletter more.

The Gazette by Freelancing Females is a weekly newsletter serving up top tips, freelancing gigs, and conversations for the world’s largest community for freelancing women.

Freelance Flow delivers leads, job opportunities, and freelance business tips to your inbox every Monday through Thursday. This newsletter is perfect for freelancers looking to take their biz to the next level!

Opportunities of the Week Newsletter by Sonia Weiser is a great resource for freelance writers who are tired of searching for new gigs. Sonia does the work for you by sending writing job postings to your inbox every Tuesday and Thursday.

Freelance Feels is a monthly newsletter full of coach and writer, Jenny Holliday’s, thoughts and experiences surrounding solopreneurial life. Subscribe for advice, camaraderie, mental health transparency, and more.

4 Tips for Breaking Up Your Day to Prevent Burnout + Maximize Productivity

4 Tips for Breaking Up Your Day to Prevent Burnout + Maximize Productivity

One of the greatest perks of freelancing is flexibility. You get to decide when and how you work. But, without a manager to keep you accountable, it’s easy to take on way too much work or let things slip through the cracks — especially if you’re new to the game and still learning what “manageable” really means.

Whether you’re procrastinating, burnt out, or just overwhelmed by tasks, here are four simple tips to help you optimize your productivity and operate as your best self.

How to Break Up Your Day to Beat Freelance Burnout

Tip 1: Determine when you work best.

As a business owner, flexibility is your greatest tool. You have the freedom to set your own hours, so why not make your schedule work for you? The key here is to determine when you’re feeling the most energized throughout the day. Are you most creative in the morning or after lunch? Practice tuning in with yourself, and use your most productive hours to knock out the projects that require the most brain power. Daniel Pink’s novel When is a must-read if you’re looking to optimize your days.

Tip 2: Make a daily plan.

As a chronic procrastinator, one of the greatest tips my therapist ever gave me was to plan out every day in its entirety. This sounds tedious, I know, but trust me. It’s a super easy lift and it makes a world of a difference.

Towards the end of your work day, pull out your favorite notebook and write down what you want the following day to look like. Start with what time you want to wake up and continue throughout the day from there. Here’s an example to help get you started:

Wake up: 7:00am
Feed dogs and make coffee: 7:15am
Take dogs for a walk + listen to podcast: 8:00am
Sign on for work + focused work session: 9:00am
Make breakfast: 10:00am

You get the idea. This visioning exercise helps you get ahead of tomorrow by laying out a practical plan today.

Tip 3: “Eat the frog.”

Hear me out… Imagine you have to eat a frog today. Yes, an actual frog. Would you do it first thing in the morning or would you wait all day long, slowing building more and more dread? Probably first thing, right? It’s like ripping the bandaid off.

The same thing goes for your tasks. Knocking out the toughest, most annoying item on your to-do list at the start of your day alleviates stress and helps you build motivation and momentum to carry you through the rest of your day. If there’s a blog post you’ve been putting off writing or clerical work you’re avoiding, try tackling it first.

Another method we love is called task stacking — you pull together related tasks and knock them out sequentially. For example, you might tackle all of your administrative tasks first, then move to your more creative tasks, then spend your afternoon conducting outreach. We like this system because by keeping related tasks together, you’re completing an entire section of your to-do list rather than going at it task by task.

Tip 4: Not feeling productive? Step away.

Sometimes the best thing you can do for your productivity is to take a break from it. If you’re sitting at your desk and you’re just not getting anything done, it might be time to take a break. Pick up a book, take a walk outside, or make your favorite lunch.

While this switch can take some getting used to, especially if you’re still stuck in that hustle culture mindset, we promise it will help you create some of your best work. By stepping away when you’re not being productive, you’re making space for yourself to do other things that fill your cup. Your work will still be there when you get back.

Freelance Lessons Learned: The Co-Founders of Harlow Share All

Freelance Lessons Learned: The Co-Founders of Harlow Share All

As freelancers, we’re always learning. (Cue “the journey never ends…” quotes.) But in all seriousness, Andrea and Samantha know this first-hand having been on all sides of the freelance journey.

Not only have they been freelancers themselves, and are very familiar with riding that freelance roller coaster, but they’ve also hired freelancers while working in-house. Now they’ve taken all those lessons and turned them into Harlow, an all-in-one freelance tool designed to help freelancers streamline their business and alleviate stress.

Today they’re sharing all their biggest lessons. But, before we jump into the interview, here’s what you need to know about these two freelance queens.

Andrea Wildt has freelanced three different times in her career. She was an early Salesforce employee, the CMO at Campaign monitor, and is an expert in operations and demand gen.

Samantha Anderl was a first-time freelancer after leaving Campaign Monitor, where she was Head of Marketing. She spent four years freelancing before building Harlow with Andrea.

As you can tell, these ladies have a lot of experience to share, so let’s skip to the good part… (All our Instagram Reels junkies know this reference!)

We're always learning on this winding road we call freelancing.

1: What’s one important lesson you learned while trying to figure out who your ideal client was?

AW: Early on in my freelance career, I would take on almost any project that came my way. I know so many freelancers can probably resonate with this. My ideal client was one who had a job to be done and could pay me! The challenge with that approach, as easy as it was, is that I wasn’t necessarily applying my learnings from one client to the next since they were so different and every project was bespoke.

When Samantha and I founded Interimly, we found that by focusing on a specific type of client, we could deeply immerse ourselves in that stage of growth and bring more to the table for future clients. And this was SO much more fulfilling. While each project still had a very custom deliverable, we deeply understood the stage they were in and the unique challenges that they faced being an early-stage company with high growth targets.

Nailing down an Ideal Client Persona (ICP) like this, rather than just taking what hit our inbox, helped us to create some repeatable processes and frameworks that better served our clients—and us too. If you’re like us, you love processes and this was a big part of creating those juicy workflows.

SA: When Andrea and I first started Interimly, we knew the services we wanted to offer, but weren’t sure about the size of the company we wanted to work with. We had just come from a 200M company and knew we could help an organization of that size, but quickly realized something incredibly important: we didn’t actually want to.

Too many stakeholders made it difficult to get things done and we wanted to be nimble so we could have a greater impact for our clients. So then we went the other direction: working with brand new companies that didn’t have any marketing structure set up at all.

This brought its own set of problems (insert face palm emoji) because we didn’t always have a point of contact or a person on the team who understood the value of marketing or the resources to get things done. If you’ve been there before, you know this makes it very hard to do your best work.

Luckily, we found that our sweet spot was actually right in the middle: working with early-stage companies that had a marketing lead already. This gave us the right point of contact so we were able to have the impact we knew we could.

Overall, we had to learn from projects that weren’t as fulfilling to figure out what an ideal project and client looked like. #Alwayslearning, right?

2: What did you learn about communication in your years of freelancing?

AW: I learned early on that the best way to make a client happy is to do what you say you’re going to do. It sounds so simple, but not all freelancers (or employees, for that matter) do this. For me, this means being crystal clear in the statement of work about the parameters of the project. Putting everything on paper is key!

Actual deliverables and timelines, along with how and when you will meet with them, should be documented upfront and agreed upon before you start the project. This provides you with a very clear document that you can reference if things start to go sideways and get out of scope. It also acts as a handy reminder to keep you on track!

SA: One thing I had a difficult time with was figuring out the communication channels that worked best for me. With email, Slack, other chat tools, meetings—it can be so overwhelming managing it all! I made the mistake early on of always meeting my clients where they wanted to communicate.

That often meant being in my client’s Slack channel where the expectation was quick and immediate responses at any point during the day—which I was not here for. I had to remind myself that I was in control of my path, and could restructure how and where I communicated with clients based on what worked best for me.

So I shifted to outlining communication channels up-front and discussing expectations with clients so we were aligned out of the gate on where and how we would be communicating.

I also learned easy responses when communication was too frequent or difficult to manage. Phrases like, “Let me get back to you on this” or “This would be more productive to chat through in-person, here’s my availability” became staples.

3: Pricing is SO hard! What have you learned about pricing?

AW: The biggest learning for me here is that it’s okay if you’re “too expensive” for some clients. Even more importantly, it’s okay to not take every project. Honestly, as you progress in your freelance career, your expertise and value do become greater and that means not everyone is going to be able to afford to bring you on. That’s a good thing, it’s how you grow and scale your business!

I also want to remind you of another important lesson I had to learn: it’s okay to get pushback on pricing. If you don’t get push-back, that probably means you’re not charging enough. (If you’re struggling with this, check out our guide on how to figure out your pricing!)

SA: When we first started out, we charged hourly for our services and that was a nightmare. We had to keep track of our hours closely, and worse, do a lot of justifying around what we were spending our time on.

So we made a big decision in our first year of freelancing to switch over to project-based pricing. What a relief! This switch not only allowed us to sell our value early on—and not fight for our pay by the hour—but it also allowed us to charge more for the services we were offering. And to be honest, we got WAY less push-back!

It may be hard to shift to project-based pricing if you aren’t confident in the value you offer, or are worried about clients fighting it. We totally get that! But we really learned to trust our gut on this.

Remember that pricing is a journey. You may not get it right the first time, but you can always tweak as you go.

P.S. We also created a pricing guide to help you along the way!

4: How did you learn to own your schedule and manage your time (and boundaries!) as a freelancer?

AW: I’ll be the first to say, this is not my strong suit! I’m very much a people pleaser and have a tendency to agree to meetings even when they’re not convenient for me, just to make sure the client is happy. (And it’s exhausting!)

Having a child during the pandemic really forced me to create stronger boundaries since I couldn’t be available all the time. A great tool for creating these boundaries with clients upfront is the statement of work that I talked about earlier. Letting clients know when and how to communicate with you upfront really does reduce a lot of the issues with scheduling during the engagement.

SA: I went into freelancing because I wanted more flexibility and greater control of my schedule. Yet my schedule quickly got out of hand when I started freelancing. As I mentioned earlier, I was often letting clients dictate when and where we connected and that left my calendar scattered.

To fix this problem, we started scheduling all of our meetings on one day of the week. This sounds so simple (and it is), but scheduling all our calls on Tuesdays gave me the rest of my week to strategize and execute on client work. More importantly, it gave me space for self-care, and time with friends—more opportunities to truly fill my cup so I could be a better freelancer for my clients and myself.

The best part is that anyone can do this. Try scheduling all of your meetings on one or two days of the week and see how much more you can get done when you have uninterrupted work and free time.

5: Generating new business is so important. What have you learned about drumming up new clients?

AW: Our business, Interimly, was based largely on referrals and our network. Specializing in early-stage SaaS also allowed us to build relationships with some VC firms that would introduce us to their portfolio companies when they had needs we could solve.

I would also like to stress that a lot of our business came from referrals from other freelancers—the power of community is immeasurable as a freelancer! Creating a mutual referral relationship with your peers can be wildly beneficial.

SA: Don’t be afraid to ask for referrals! We always asked our clients at the end of projects to please recommend us to anyone they knew in their network looking for a similar project. We know this can be so hard to do—cue that squeamish, uncomfortable feeling of asking for something! Trust us on this: it’s worth it. Sometimes you have to remind people to refer you out, and at the end of a project, especially when it ends on a high note, is always the perfect time to do that!

So Many Lessons Learned—and Still Learning

Andrea and Samantha have learned so much during their freelance careers. As we all know, it’s an ever-evolving journey—and there are still plenty more lessons for them to learn along the way. If you want to accompany them as they navigate the ups and downs and turnarounds, follow along on Twitter, @meetharlow, @samanthaanderl, @thelittlestflea, on Instagram, @MeetHarlow and @samanthaanderl, or on LinkedIn, Harlow or Samantha’s profile.