Freelance Interview Series – Getting Into a Business Owner Mindset with Ashley Cummings

Freelance Interview Series – Getting Into a Business Owner Mindset with Ashley Cummings

by | Oct 14, 2022 | Blog, Resources

Ashley Cummings is a freelance writer and content marketer with experience in DTC, SaaS, and more. She recently shared 11 lessons learned over her decade of freelancing in her newsletter, and we wanted to dive deeper and share her knowledge with you!

Thinking Big as a Small Business Owner

1. What are 1 or 2 of your top methods that helped you get into a true business owner mindset?

Thinking big is primarily what helped me get into a business owner mindset. We often limit ourselves sometimes by thinking small.

For example, we may think $250 for a long-form article is a lot of money, because we can buy a lot with $250, and it may be a lot of money to us personally. But, it’s not a big expense for your client. Instead of thinking what $250 means to you, think about what it means to a big company (nothing), and consider how much expertise and value you’re providing. That one article you write could bring your client several new customers worth thousands and thousands of dollars each. Charge accordingly.

Also, thinking big isn’t limited to how much you charge. It can also mean thinking about growing your business. What are other ways you can scale and diversify your income? Can you start and monetize a newsletter? Build a community? Create software? Partner with other professionals on cool projects?

When you think big, you create and earn big, too.

2. How have you leaned on your network to grow your freelance business?

Networking with other freelancers and content marketing professionals has been the single most important thing I’ve done to grow my business. When I started freelancing, the first place I went to get new clients was to my network. I did some work for previous companies, marketing friends, and even some of my dad’s advertising friends.

As I’ve grown as a freelancer, I’ve made it a priority to make friends with freelancers who have similar clients and who work in the same niche as me. It’s also essential to meet up in person and develop real friendships. These are the people who I refer work to and who refer work to me. Not only do I refer work to these other freelancers, but I’ve partnered with several of them for new business initiatives.

I always say people can’t hire you or refer you if they don’t know who you are. Carve out time to introduce yourself and build relationships.

    3. Talk to us about some important boundaries you’ve set with clients over the past 11 years.

    One of the adjustments I had to make moving from a 9-5 job to freelancing is to realize I’m the boss of a business and not an employee of my client’s business. This significantly changes how you interact with clients.

    Before I start any project, I take the lead and set expectations of how my processes work, how/when I respond to emails, what my turn around times are, what project management processes work/don’t work for me, and what my payment terms are. I also reinforce this by making sure my clients sign my contract.

    I think the most important boundary I’ve set is defining my payment terms before I start a project. If I’m working with a large organization that has an accounting team, I am flexible with their processes. For example, I like to get paid Net-0, but sometimes it’s not possible if you’re working with a huge SaaS company. The important thing is to communicate your expectations, what is realistic for them, come to a mutually beneficial agreement, and write it into your contract.

    Another boundary I set is when I need assignments and turn around times. I juggle 10+ clients every month, so it’s rare that I can take on a last minute assignment (sometimes, I can, but it’s rare). I ask my clients to send all the assignments they need in a month by the last week of the previous month. Then, we schedule due dates throughout the month that work for me, them, and my other clients. By planning a month in advance, it gives me and my clients enough time to realistically meet deadlines.

    4. Logistically, what were the most valuable things you did when first setting up your freelance business?

    The most valuable thing I did was set up a website and consult an accountant and a lawyer. It’s really difficult to stand out as a freelancer if you don’t have a website where you showcase your work. It adds credibility and shows clients you know how to write. In terms of setting up a business, there are a lot of things I do know how to do, but writing a contract and accounting aren’t part of my skill set. It was invaluable to hire professionals to handle my taxes and write my contract.

    5. What advice do you have for those at the beginning of their freelance journey?

    I would say make networking a priority. Join Twitter, LinkedIn, communities, and go to events IRL. The more friends you have, the more opportunities you’ll have to learn and grow. I also advise new freelancers to establish systems and processes to keep their business organized.

    Freelance Interview Series – Growing Your Freelance Business with Alexandra Frost

    Freelance Interview Series – Growing Your Freelance Business with Alexandra Frost

    by | Sep 13, 2022 | Blog, Resources

    Alexandra Frost is a journalist, freelance writer, and mother who has a passion for teaching and training young journalists. Her self-motivation and ability to achieve work-life harmony are just a couple of ways that she inspires us. She’s also grown her freelance business from $300/mo to $25,000/mo in just three years!

    We asked her to share her experience growing her freelance business and building her dream career.

    Building a Dream Career and Business

    1. What were your goals when you first started freelancing?

    My first article was published in my local paper at age 18 for $15, and it was a news brief about a local American Idol competition. Through college and my 20s, while I pursued a career in education, I used freelance writing as a side hustle, a passion project, and something to do for fun.

    While I loved teaching, especially teaching journalism, I still had a hunger to write more. When a news event would flash across the TV, I’d feel out of the loop that I wasn’t covering it. So I started freelancing with our city’s news station and newspaper, taking a story per week.

    My goals expanded and I started my own business doing freelance journalism and eventually content marketing. I wanted to cover the news and feature stories/trends, but I also wanted to get involved with the company’s missions, help them achieve their content goals, and feel like part of their direction and success.

    During the pandemic, when I switched to virtual teaching, I had much more time and greatly expanded my business- helping other businesses pivot their content to be pandemic-relevant. Shortly after, I had my fourth son and quit teaching, going full-time freelance, thriving in the flexibility of my new schedule and the creativity it allowed.

    2. Did your freelance goals shift over time?

    Yes. As my sons grew, and joined sports and needed cool shoes, and as I save for their colleges and prioritize date nights and short trips with my husband, money became a much larger factor. I went from making $300 per month freelancing a few months ago to my first $20,000 month this August while working part-time hours.

    I continue to be shocked and excited about how my business can support my growing family and the security it provides, in spite of the bad rap writers and other small business owners have for not having financial success (a myth!). Making more money than I could as a teacher was always a goal, and is now a reality.

    Many people think money is not an indicator of success, and while that is true, it’s wildly helpful in supporting my family and doing things I want to do in my life. Additional indicators I pay attention to, and prioritize as goals alongside that, include:

    • Working with companies and publications I believe in, who I think are making a difference or have strong ethics
    • Working with editors and project managers I find pleasant, challenging, and excellent to collaborate with
    • Finding a variety of interesting work that keeps me looking forward to sitting in the chair each morning and opening my computer
    • Proposing stories that matter personally to me

    3. You work part-time and have seen your business grow exponentially, do you have any scheduling tricks and tips to share?

    I set my schedule around the amount of time I prefer to work and parent, which for me is 50/50. I work Monday through Thursday, after spending time with my kids for breakfast, from 9 AM-12 or 1 PM. Then I have lunch with my kids and put them down for nap time.

    Having that time to run my business without them at home is essential to being able to Zoom and interview in peace. From 2-4 PM I do tasks that don’t require phone calls, such as writing articles, responding to publicists and sources, pitching, and research. Sometimes on busy days, I work until 5 PM.

    I reserve Fridays for fun outings with my family or professional development for my business that I don’t consider work, such as learning through reading my favorite writers’ articles, listening to a podcast while on a walk, or following interesting leads on social media. This results in approximately 20-25 ish hours of work, depending on the week.

    My biggest tip is to combine your availability for calls into a narrow window to give the rest of the day more flexibility. I also have a pretty hard rule against working weekends, evenings, or during vacations, though if I decided to go to the pool all afternoon with my kids, sometimes I’ll fit an hour in later in the evening instead.

    4. Were there any pricing and packaging shifts you made as your business grew?

    I have raised my rates throughout my career, as I am able to offer more prestigious clips and work experiences to new clients. I went from that original $15 story to recently a branded content piece for $3 per word. I believe in constantly reassessing rates (we have to pay our bills, after all).

    A mentee in my earliest years taught me to always negotiate, and that’s a rule that has served me incredibly well over the years. There have been a handful of times I didn’t negotiate rates, but overall it’s a process for me that ensures there’s no money left on the table for the work I’m providing.

    I also expanded to offer media consulting to publicists, helping bridge the gap between publicists and journalists. I realized they often feel they are shooting out pitches without much information on what would most benefit journalists, so I decided to work with them.

    I also provide freelance and business coaching to new and mid-level writers, helping them pursue this career path, and I mentor young journalists. This is one of my favorite parts of my job, as I still love teaching.

    5. What advice would you give freelancers just starting out who can’t clearly see a path to more money and a sustainable career?

    First I would identify what barriers you perceive to be in the way. Here are a couple of challenges the writers I coach and mentor talk about and some I’ve been through myself.

    “There aren’t any clients/publications interested…”

    This is very tough. I’d look at this as a five-year goal rather than something that will be solved next month. And every year within that five years, you will be surprised to have more clients coming to you than the previous year. Make pitching a hobby, a way of life, and a go-to activity that you do when you need a break from your other tasks.

    I truly believe my business’s success is because I love the chase, I love reaching out to new clients or publications and learning what they want and how to pitch that, or provide that to them. Constantly pursuing new opportunities (daily, weekly) will result in many no’s, but eventually many yes’s.

    “I don’t know how to do XYZ…”

    Fake it til you make it has never been more true. If you know how to communicate, research, and write, you can figure out a lot more than you think. I didn’t know the first thing about medical devices, and now I contribute copywriting to a major health tech company. I didn’t know much about fashion, but then I was writing blogs for a top NYC stylist and a well-known fashion line.

    If you are confident you can do the work, do a ton of research to educate yourself, and make it happen. I’ve also built a community along the way, from freelancing friends I text with regularly to online communities, chat boards, and coaches I’ve paid to learn from. All of these help along your journey of self-education and collaboration.

    “I don’t know my niche.”

    Well, neither do I. I highly disagree with people who say you have to have a single niche, because I don’t, nor do I want to. I definitely have areas I focus on and am passionate about, such as health and wellness, parenting and kids, and education. But I’ve also written about dog food, medical claim denials, camping, and sustainability this month. While it helps to narrow down your passions, don’t count yourself out for projects that aren’t your typical path. This also helps keep every day fresh and exciting – ultimately preventing burnout.

    “I’m not sure where to find opportunities.”

    Sign up for newsletters where people post jobs, such as Sonia Weiser’s and Write Jobs Plus, along with following editors and marketing leads on Twitter and LinkedIn. Every piece of junk mail you receive via mail or email came from a marketing team. Reach out to them and introduce yourself, and share a few relevant links to projects you’ve worked on.

    Finally, consider the connections sources themselves have. They might have a friend at a similar company looking for a blogger, copywriter, etc. Ask editors and marketing professionals you love if they’ll pass your name along to others in their network. Gather testimonials as you go to display them on your website/portfolio. Finally, speak confidently about yourself, your business, and your services, and others will be attracted to that confidence.

    How to Track Business Expenses & Why It’s So Important

    How to Track Business Expenses & Why It’s So Important

    by | Sep 13, 2021 | Freelancer 101, Guides

    When tax season rolls around, so does freelancer dread. It’s time to count up all the expenses you forgot to log and figure out how to calculate your home office deduction. The process is filled with obscure questions and hazy requirements. Does the bathroom count in my home office square footage? Can I write off my vacuum cleaner? What about that label printer I bought when I was procrastinating on filing my taxes last year?

    Filing taxes as a freelancer can be anywhere from hellish to mildly inconvenient, depending on how diligent you are about tracking your business expenses and how educated you (or your accountant) are in tax law. Because the process is confusing and aggravating, many freelancers are less than thorough when it comes time to claim business deductions. In fact, 73% of freelancers overpay their taxes because they don’t claim any deductions at all.

    That sucks. That means loads of freelancers are losing out on money that they could have in their pockets right now. And we don’t want that. So in this post, we’re going to show you how to track business expenses seamlessly and keep more of your income. Here are the five key steps to doing it right.

    73% of freelancers overpay their taxes because they don’t claim any deductions at all.

    1. Educate yourself.

    The biggest challenge with filing taxes is that most of us just don’t know the rules. That’s no fault to us—people spend years learning this stuff. But even without a degree in accounting, you can get by with a little basic knowledge on tax regulations. Learning what qualifies as self-employed expenses is step one. The IRS says that any “ordinary and necessary” expense can be deducted from your taxes. That essentially means any expense that is necessary to run your business, like your software, cell phone, WiFi, and any subscription services you use for work.

    If you’re working from home, be sure to factor in all of the hidden expenses that come with managing your home office. You can deduct office furniture and essential equipment, like a new computer, chair, or printer, as long as you’re using them for work. And (importantly!) you can factor in the basic costs of living that contribute to your work. For example, if your office area is 30% of your total living space, you can count 30% of your living expenses (like rent and utilities) as business expenses.

    What else? Insurance premiums and certain types of retirement savings are also deductible. There are likely a whole host of other deduction opportunities for you too, depending on where you live and what kind of work you do. For example, if you use your car for work, you can typically deduct the cost of gas, so logging your mileage is smart.

     

    Hot tip: The app MileIQ is great for logging mileage because it automatically tracks your trips and creates a comprehensive record that you can reference come tax time and, if necessary, submit to the IRS for proof.

    2. Open a separate bank account.

    This one is so easy to skip over as a freelancer if you’re only paying yourself. Why not just deposit everything into your personal checking? Well, it makes everything a whole lot easier come tax season if you have a dedicated bank account for your business. Even if you don’t have an LLC, we highly recommend opening a checking account. Seriously. It’s a huge relief when you can view all of your income and expenses in one place, and just download an account statement to submit along with your taxes.

    If you’re spending more on your business than you’re earning and you’re worried about overdrafting, you might want to consider getting a business credit card to pay your expenses. There are loads of credit cards for small businesses that offer cash back rewards and low annual fees (or none at all). Again, having a dedicated credit card for your business instead of mixing personal and business expenses will save you many headaches down the line.

    3. Keep all of your receipts.

    I know, I know. It’s a hassle. But even freelancers can get audited by the IRS, and sometimes that bank statement just isn’t enough. Shove your receipts in a shoe box and let it gather dust in the closet for four years. Or, just use a tool like Expensify to snap a picture of your receipts so you can go paperless. The IRS will accept photos or physical copies.

    4. Stay organized.

    It will make your life infinitely easier if you spend 30 minutes a month organizing your expenses rather than waiting until the end of the year to scour your statements and figure out what all of those random charges were from. Plus, reviewing your finances regularly helps you catch erroneous charges and forgotten subscriptions when there’s still time to cancel them.

    Reviewing your finances regularly helps you catch erroneous charges and forgotten subscriptions when there’s still time to cancel them.

    If you’re not a log-expenses-as-you-go kinda person, try putting time on your calendar once a month to do this. Create a recurring monthly event in the first week or so of the month to review last month’s finances and log your expenses in your system of choice. You can use something as simple as a Google Spreadsheet or something more sophisticated. At Harlow, we’re working on bringing all of your bank account expenses into a single place, so you can easily categorize and organize your finances from one dashboard. Stay tuned!

    5. File your quarterly taxes!

    Finally, don’t forget about those four dates a year when you owe the IRS. As a freelancer, you aren’t just responsible for paying your income taxes. You also owe self-employment tax, which is 15.3% of your net income. (This is another good reason to log and deduct expenses!) The IRS expects you to pay taxes on a quarterly basis, so be sure to mark those tax dates on your calendar now, before you forget.

    If you have all of your business expenses in a separate bank account, it’s easy to prepare for quarterly taxes. A little recommendation: Link a savings account to your checking account and transfer 25%-30% of your income into that savings account each month, so you have more than enough cash on hand to pay your quarterly taxes throughout the year. Trust us: There’s nothing worse than getting stuck with a huge tax bill and late penalties come spring. Save as you go and you’ll save yourself the stress.

      Trust us: There’s nothing worse than getting stuck with a huge tax bill and late penalties come spring.

      We know managing finances can be one of the most overwhelming parts of freelance life. But with a little practice and a good system, it can be pretty painless (or dare we say… fun?). Like any other unpleasant activity, tracking expenses and filing taxes is a whole lot more pleasant when you focus on the ‘why’ (e.g. planning for the future) and do whatever you can to make it more pleasant. So when it comes time to scour your statements each month, grab your beverage of choice, put on a great playlist, and channel your inner accountant. You got this.