I wish I could say I set out to start my own business intentionally… but truth be told, it just sort of happened. I feel really lucky that my professional stars have aligned over these past few months and provided me with the opportunity to branch out on my own into the world of consulting and freelancing—but it was definitely more of an accidental stumble than a carefully planned decision.
And so, inspired by my friend Lauren Drell—who wrote an excellent Medium piece on the questions she’s been asked most since starting her freelance journey, and another on the 11 things she learned in her first year as a freelancer—I thought I’d round-up the essential tools and resources I couldn’t have done without over my first quarter as an independent worker.
I should also preface all of this by saying I am by NO means an expert on taxes, finances, or any of the advise I’m casually dishing out below. These are all personal opinions and suggestions, and I absolutely recommend consulting with professionals in the space before getting started.
1. ZenBusiness
First things first: Setting up an LLC. There’s tons of great information online about the differences between LLCs, S-Corps, and C-Corps (case in point: this guide from Inc., which is an oldie-but-goodie), so I won’t get into too much detail here, but my first order of business (so to speak) was deciding what kind of entity to form—and where.
Several friends who’ve set up their own businesses before recommended I register my company in Delaware because of the tax structure, but for the sake of simplicity and logistics, I opted to keep my business affairs local in Colorado. To be totally honest, the complexities of filing in both Delaware and Colorado and assigning a registered agent in two places overwhelmed me; I’d suggest consulting with a professional about tax implications before deciding which state to register in. (Full disclosure: something I didn’t do but wish I had.)
Anyway. Back to the company formation process. There are so many websites that offer LLC registration, with ZenBusiness, LegalZoom, and Northwest among the companies recommended most often. After some VERY deep Google rabbit holes, I went with ZenBusiness, and I’m so glad I did. They handle everything for you: preparing and filing your LLC, annual report services, operating agreements, EINs, DBA services, and so much more. I already had a business website and email address set up, but for those who are new to that as well, ZenBusiness also helps with domain name purchase and email integration. There was excellent, prompt customer service support when needed (though the process was pretty seamless.) Truly can’t say enough good things about them.
(Side note about the business address: I ended up renting a mailbox through UPS since USPS doesn't allow you to legally use their street address for business purposes and I didn’t want to make my home address public.)
2. Wingspan
Once I got past the name (IYKYK), I realized Wingspan is a freelancer’s godsend. Their tagline is “Everything you need to freelance” and that TRULY couldn’t be more accurate. It’s a one-stop shop for sending client invoices and tracking payments, bookkeeping (who knew taxes as a freelancer were so complicated?), health insurance benefits and retirement savings, and so much more.
They also have tools like an hourly rate calculator (more on this in a future blog post!), a quarterly tax calendar you can subscribe to so you never miss a payment deadline, and a robust resource hub with helpful template forms to create everything from NDAs to consulting agreements to contracts.
You can register for a demo here, and you decide to sign up, here’s my referral code. (After the 14-day free trial, we’ll both get $50.) I swear I’m not being paid to say any of this—I just can't recommend it enough.
Note: There are comparable platforms and services out there, like Bonsai and HoneyBook, both of which I’ve heard great things about, but from the peers and fellow freelancers I’ve spoken to, Wingspan is by and far the winner. My vote is not to bother with QuickBooks—you can get that same functionality from any of these three alternatives.
3. Calendly
I’m pretty sure Calendly has saved me at least five hours of back-and-forth email scheduling in the last quarter—and that’s probably a conservative estimate. Like, I’m sort of unclear on how I functioned before using Calendly; It’s SUCH a game-changer for scheduling meetings. All you have to do is link your calendar(s) (the premium plans let you integrate multiple, which is so helpful), set your available hours (you can vary them by day), choose the event types you’d like to offer, customize your personal link, and voila.
You can take it up a notch with Zoom and Google Meet integration (a must!); there are also automations for custom workflows (think meeting reminders, thank-you emails, text confirmation, surveys, etc.) and lots of helpful integrations (e.g., Stripe, Salesforce, HubSpot, Mailchimp, etc.). I can safely say Calendly’s pro plan has been worth every penny.
4. Toggl
I’ve used Toggl for years—even in my non-freelance jobs—and it remains one of my favorite productivity tools. On the freelance front, I’ve found Toggle Track essential for calculating time spent on each client and project. Sure, I could just use a regular old clock or timer, but is that as organized or visually appealing? Nope.
Like so many of the other tools featured here, Toggl offers tons of integrations and premium add-ons, but truth be told I only really use the timer feature and regular analytics reports, and have found that the free version is more than sufficient for my solopreneur needs.
5. Notion
People having been raving about Notion for a few years now, but until recently, I was a bit skeptical. Getting used to a whole new interface sounded like an adjustment I didn’t have the patience for. After all, what was wrong with Google Docs and Google Workspaces?
Everything, as it turns out.
After a bit of a learning curve, I’m officially on the Notion bandwagon and can safely say I’m never getting off. (Unless, you know, the platform ceases to exist.) It’s SO beautifully designed and sophisticated and intuitive with its note-taking capabilities and nested pages. It’s not that the tool is critical for freelancing, per se, but not even two months into using it, I can’t remember how I stayed organized without it.
Notion calls itself an “all in one workspace,” which feels 100% accurate. From organizing notes and documents to managing projects and tasks, building out content calendars and style guides to mapping out approvals and to-do lists, it’s truly a powerhouse. And there are beautiful (free!) templates to help you get started. One of my favorite things about Notion is that it’s just as effective for personal use as it is for professional use.
6. IndeCollective
Last but not least, IndeCollective. This one’s a long one, but please bear with me.
When Sam Lee, a former WeWork colleague and overall rockstar of a human being, reached out to me a few months ago about a new startup he’d created, I had no idea it was going to change the course of my career—quite literally.
Some background for those who don’t know me: I left my role at WeWork in May of 2020, after 5+ years at the company (more on that decision here). I was fortunate enough to take some time off afterward to recharge and do some soul-searching—a privilege I don’t take lightly. I told myself I’d use a full six months to regroup before even approaching the job search, at which point I’d be refreshed and energized and have a newfound sense of clarity and purpose.
Things I didn’t take into consideration: Reality. A global pandemic. The toll that 2020 took, both mentally and emotionally, even though I was fortunate to be safe and healthy and to say the same for my loved ones. By the time my self-imposed six-month grace period drew to a close, I hadn’t had a single breakthrough or a-ha moment. And so I procrastinated, setting Q1 2021 as my new deadline for landing a job.
But, as they say, man plans and God laughs. By mid-April, I was in my fourth straight month of job-searching and interviewing and take-home assignments (which… more on that another time). As the founder of The MarketHer I felt a little silly—here I was running a newsletter aimed at helping other women find meaningful work, and yet I was struggling to even figure out what I wanted for myself. None of the full-time opportunities I’d had my heart set on were panning out: I was either too senior or too junior, or the recruiter didn’t find my skill set transferrable, or I realized way late into the process that the role I was chasing was causing more anxiety than excitement.
And that’s when Sam reached out—somewhere in the space between stuck and discouraged, still yearning for a strong gut feeling or magical sign from the universe about what I was “supposed” to be doing.
Sam’s new company, IndeCollective, was born from his desire to help fellow independent workers translate their specialized skills into successful businesses and achieve better balance. Through the program, he brings together a curated group of talented independent practitioners and agency-builders, and, over a carefully planned 10-week course comprised of workshops, breakout groups, and programming, provides the cohort with the education, expert guidance, and supportive peer group they need to take their independent work to the next level.
Sam and I hopped on a call on a Thursday, and by Friday, I was unstuck—maybe not in the way I’d envisioned in May of 2020, but he helped spark something that excited me: the prospect of pursuing my own path instead of going back in-house full-time. And with that, my new plan began to crystalize. I took Sam up on his offer to join the IndeCollective Spring cohort in exchange for helping with their social media strategy and content—and oh. my. goodness. I’m so glad I did.
I truly can’t say enough good things about the program. (And I’m not being paid to say them—I just wholeheartedly believe in it and in the work Sam is doing.) The foundational basics (pricing, productization, scaling, networking, developing a bulletproof psychology, and so much more), coupled with the incredible people I met through the workshops, breakout sessions, and our weekly (A) Team meetings, made my transition into independent work at LEAST ten times easier than it would’ve been had I started down the path alone. As many others before me have pointed out, freelancing can be lonely—but as Sam likes to say, “independence doesn’t have to come at the cost of community.” I’m beyond grateful to have had the support of the IndeCollective community as I set about my new chapter.
If you’ve read this far, THANK YOU. Have any recommendations for other tools and resources you’ve found essential as a freelancer or independent worker? Leave ‘em in the comments below!
