Freelance Interview Series – Being Your Own Best Boss

Freelance Interview Series – Being Your Own Best Boss

by | May 2, 2023 | Blog, Resources

Corrie is a solopreneur with over 22 years of digital marketing experience and 17 years of experience developing social media campaigns. She also has a newsletter, Chaos Freelancer, where she discusses the ups and downs that come along with the freelance career path and being your own boss.

How to Be Your Own Best Boss

Talk to us about what being your own best boss means to you. 

Being your own best boss means being a good steward of the only resource I have as a solo marketing person – me. That means making sure that I’m:

  • Taking on projects that interest me & meet my financial needs,
  • Working a reasonable amount of time on those projects and not letting work overtake everything else,
  • Giving myself growth opportunities by investing in learning & training opportunities – sometimes in my field, sometimes outside of it,
  • Actively prevent burnout by hanging out with family & friends, doing things I like, resting – basically having a life,  
  • Not saying yes to something in my work life (meetings, networking events, tasks, marketing activities, etc.) that take away from what I really need to do,
  • Make sure I get enough sleep, enough to eat, and enough movement in my day. 

How has your definition of being your own best boss shifted throughout your years of being a business owner?

When I started freelancing, I had spent almost 8 years in a marketing agency lifestyle, which left me burned out and overworked. So you’d probably think that would mean I’d actively avoid making the same mistakes, right? 

Wrong. I repeated my agency experience but in my own business. I thought more hours = better. More clients meant more success, no matter what it did to my personal life. 

I thought I was my Best Boss by making myself do all these ridiculous things, but I was my own Worst Boss. It took me about 5 years of work on myself & my business to realize that to make my business sustainable; I had to start prioritizing myself. 

How have your values shifted as you’ve progressed in your freelance career?

I used to value what other people thought of me SO MUCH. So to get more work (or to keep the work I had), I thought I couldn’t “rock the boat,” and said yes to meetings or networking events I didn’t have time for, agreed to deadlines that didn’t work for me, allowing way too much scope creep in projects, or even working through vacations. I let myself be pulled in 1000 different directions not to make waves or disappoint people.

About five years ago, I realized that clients who valued me, my work, and my time would understand if I had to say no, move a deadline, or take time off. By putting myself first – yes, even over client requests – I’ve been much happier (and get so much more done). 

It’s so important to celebrate wins! What are some ways that you celebrate your own wins at work?

Celebrations are one of the things I’m still working on. More than celebrating, I’ll often make sure that I take time off after a big deadline (even if I’ve got other competing deadlines). I also usually celebrate by napping, because in addition to working for myself, I’m also a parent, and naps are gold.

What are some of your best practices for preventing burnout?

  • Take on only what you can handle. Period. This may mean turning away work, but you do yourself more harm than good if you accept more work than you have time or capacity for. 
  • GET YOURSELF A HOBBY & engage in interests outside of work. Have you ever been stuck at a party talking to the one person who only wants to talk about their job? It was super boring, right?  Find something you can engage with that isn’t your job. 
  • Prioritize rest. Rest can mean sleep, sure, but also vacations, time off, WEEKENDS, no-phone days, etc. 

What advice do you have for those just stepping into being their own boss?

It isn’t easy, and it is OK. I’ve been freelancing for almost 15 years, and I didn’t realize until 5 years ago that I was a terrible boss. Whatever point you are at in the journey, if you are taking steps to be a better steward of You, then that’s a better place than you were yesterday. 

What advice do you have for those who want to become their own best boss?

If you are just starting, remember that even though you are working for yourself, on your own, that culture matters and that your freelance business HAS a culture. Think about the kind of workplace you want and then take active steps to make that type of workplace happen. 

Freelance Interview Series – Building Relationships Methodically

Freelance Interview Series – Building Relationships Methodically

by | Apr 27, 2023 | Blog, Resources

Tim Noetzel is a freelance web developer and designer, business coach, and founder of Freelance GPS. Follow along with Tim on Twitter and subscribe to his newsletter to get his top tips for growing a successful freelance business, access to his courses, and more.

A Recipe for Relationship Building

Why should freelancers prioritize building relationships?

The most successful freelancers are the ones who work with top-tier clients, the types of companies that both understand and value the work.

Because these clients understand the work, they don’t require as much hand-holding. They ask smart questions and give good feedback. They don’t change the scope last minute and they treat you like a partner.

Because they value the work, they pay premium rates. They understand the care and time it takes to produce a good result and they believe that result is worth the effort.

Every freelancer wants these types of clients, but they’re hard to find because most of them aren’t on freelance sites and job boards.

Top-tier clients are well-informed and well-connected, so they typically find freelancers through their networks. So to land these types of clients, you have to build relationships, both with the clients themselves and with other freelancers who serve them.

How do you recommend those new to freelancing get started building their community?

I cover this in way more detail in my free course, but the short version is this:

  • Find your local hubs – Look for places where your clients, and freelancers serving your clients, are hanging out. These could be coworking spaces, industry meetups, Slack groups, startup accelerators, etc.
  • Go and participate – Ask for advice from other freelancers. Provide value by teaching about your area of expertise. Ask questions of others and show an interest.

How do you determine the level of energy you put into developing a relationship with a new client or other freelancers?

In his book Give and Take, psychologist and Wharton professor Adam Grant divides people into three groups: givers, takers, and matchers.

It’s a great book and well worth a read, but the headline is that the most successful professionals are people who focus on giving wisely.

Unlike takers who are in it for themselves and matchers who view relationships transactionally, givers are devoted to giving back. But the successful ones don’t do so indiscriminately. Instead, they focus, on giving in ways where they can actually make an impact efficiently and to those who have shared goals or interests.

Essentially, they think about expanding the pie for everyone.

In a freelancing context, this means thinking strategically about your expertise, your target clients, and other freelancers who offer complimentary services.  Prioritize your efforts based on how relevant you are to them and how much of an impact you could make.

If you’re a freelance UX designer, for example, doing an elaborate favor for the owner of a solely brick-and-mortar business probably isn’t a great use of your time.

But running a free workshop for web developers on the importance of UX and how to spot common UX problems could be a fantastic way to give back. The attendees would get tons of value, and you’d demonstrate your expertise to potential clients and other freelancers.

How has prioritizing professional relationship-building impacted your career?

In terms of raw metrics, last year I earned nearly 3x what I ever did at a full time job, and 92% of that revenue was from clients who I met through referrals and other forms of relationship building.

But I think the non-financial impact has been even higher.

I have enough opportunities that I can turn down projects that don’t interest me. The clients I work with treat me like a partner, and I genuinely enjoy working with them. And most importantly, I’ve met some genuinely interesting people I never would have otherwise!

What advice do you have for freelancers who struggle to find the time to build meaningful relationships?

The nice thing about building relationships is that it actually takes substantially less time than many other approaches to marketing your freelancing.

Blogging and content creation are extremely time intensive. The so-called expert advice for freelancers on sites like UpWork is to submit 25-50 proposals per week.

But you can build relationships in just an hour or two per week.

So start small and reconnect with the people you already know and ask for introductions, or attend an industry meetup in your area. You never know who you’ll meet!

7 Conferences for Freelancers to Attend

7 Conferences for Freelancers to Attend

by | Apr 26, 2023 | Blog, Resources

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.

Freelance Interview Series – Freelancing Through a Recession

Freelance Interview Series – Freelancing Through a Recession

by | Apr 5, 2023 | Blog, Resources

Michelle Garrett is a public relations consultant, writer, and public speaker who works with B2B brands helping them secure media coverage and create engaging content. She also hosts #FreelanceChat weekly on Twitter – if you’re a freelancer looking for support, we highly recommend checking it out!

Freelancing Through a Recession

Talk to us about your experience working through past recessions. How did your business shift during those times?

Let’s see, I worked through recessions in 2007-09 and then the brief one in 2020. The recession in 2007-09 nearly put my business under. I wasn’t well-positioned or prepared for it – and it lasted a LONG time. I was also returning from maternity leave after having my daughter, which probably compounded the issue. I had to take work that I normally wouldn’t in order to start rebuilding my consulting business. It was a situation I vowed I’d do my best to never find myself in again.

The recession in 2020 was less severe. I was in a much better position and didn’t see a decline in work during that time. If anything, there was MORE demand because businesses knew they had to focus on communicating online as everything was closed – and everyone was at home, looking at social media and spending time online.

Are there any resources you can share that have helped you plan and prepare for a recession?

This may sound simple, but paying attention to the news is important when you’re running a freelance business. Look for a source you trust (maybe that’s NPR, for example) and follow the economic stories so you’re not caught unaware if a recession is on the horizon.

Also, if you can talk with a financial planner, that person may be able to help you determine how much money you should put in savings or other accounts. I finally hired a financial planner and it really helped me find peace of mind as far as how to distribute funds so that I’d be covered in the event I needed to fall back on my rainy day fund.

How do you manage the stress that comes along with economic downturns?

It’s gotten easier over the years. I think you get used to it, to a degree.

I do believe in having a financial cushion – so I try to work as much as I can during times of economic growth, just in case my business takes a turn when the economy is more volatile.

Having that savings – just in case – helps lessen the stress.

Also, understanding that the economy is cyclical helps. A recession is always coming…they’re cyclical. It may be years away or months away – but the economy goes through its ups and downs.

In what ways do you lean on your community for support during these times?

I think freelancers are lucky when they have each other to support them. It’s great if you can let your community know that you’re in need of referrals – or maybe you just need someone to talk to or to reassure you that whatever is happening currently, won’t last. Things always change, so if your situation isn’t the best right now, your community can help remind you that brighter days are ahead.

What advice do you have for freelancers who want to properly prepare for a recession?

Make hay while the sun shines, as the old saying goes. Work – and save money – when you can.

And NEVER stop networking – by that I mean meeting and talking to people. The more people you know who know what you do – and feel good about potentially referring work your way – the better. Even when you’re busy with client work, you shouldn’t neglect your marketing and networking activities.

The Ultimate Tax Checklist for Freelancers

The Ultimate Tax Checklist for Freelancers

by | Mar 27, 2023 | Blog, Resources

This is a guest post by Varsha Subramanian, of FlyFin. Varsha is a highly experienced US CPA with a background in both tax compliance and advisory.

Working for yourself means you have ultimate control – over your business, your work life, and your future – but you’re also responsible for every aspect of your business, including taxes.

When you understand a handful of the most important tips, and you have the right checklist though, taxes can become another part of your business that you have full control and confidence over. Let us lead you through our comprehensive list of everything you need to know about freelance taxes.

How to pay the lowest tax amount possible

Step 1: Find your net income

It’s important to understand the difference between revenue and net income. Revenue, also known as gross income, is the total amount of money you’ve earned from selling products to customers or providing services to your clients.

Say you’re a freelance web designer charging $70 per hour, and you bill 10 hours in a month. 10 x $70 = $700 in revenue. Net income is what you have left after you have subtracted deductible business expenses. EX: If you sell online courses as well as freelance services, and you make $100K and have business expenses of $5,000 to host those courses, your net income will be $95,000.

It’s net income that you pay taxes on, rather than the payments you get directly from clients. This is great because net income is where tax deductions come in to make the amount you owe a lot lower.

  • Identify your total revenue
  • Identify any business expenses
  • Calculate your net income: total revenue – expenses = net income (also known as taxable income)

That leads us to our next point, how to identify and find those expenses!

Step 2: Don’t miss a single deductible business expense

As we mentioned, deductions reduce your net income and in turn your taxes. In the eyes of the IRS any business expense that is “ordinary and necessary” for the industry you are operating in can be deducted from your taxes.

That leaves a lot of room for all sorts of deductions – 200+ categories, actually, and if you find them all, you can bring the amount of tax you owe way down! Unfortunately, it can be easy to miss deductions if you’re tediously searching through piles of receipts or spreadsheets looking for anything you can write off.

But if you find the right tools and keep track of your expenses on an ongoing basis, you’ll be much more prepared come tax season. The FlyFin app uses A.I. to scan your expenses to find every possible deduction, down to the tiniest write-off. And CPAs specializing in 1099 taxes are available 24/7 in the app for any questions. At tax time, they prepare and file your federal and state tax returns at no extra cost. Easy peasy!

Here are some of the most common deductions that freelancers can make:

  • Take all the home office deductions possible if you work from home.
    • Rent
    • Utilities
    • Internet
    • Office supplies
    • + many more
  • Deduct every business meal when you:
    • Court a prospective client
    • Discuss business with friends in the same industry
    • Get a referral from someone over a meal
    • Have lunch with a client
    • Network with industry experts
  • Write off expenses related to your vehicle if you travel at all for work
    • Car insurance
    • Parking fees & tolls
    • Gas
    • Repairs & maintenance, including tires & oil changes
    • Licensing and registering fees
  • Lesser known deductions
    • The Qualified Business Income Deduction
    • ½ of the self-employment taxes every freelancer has to pay
    • Expenses associated with professional education, conferences and seminars
    • Meals by yourself, if you’re on a business trip, plus other travel expenses
    • Music or video streaming subscriptions, if they’re for your clients

Freelancers can take deductions in over 300+ categories! Make sure you’re doing the work up-front to keep more of that hard-earned cash.

Know which taxes you need to file as a freelancer

Step 1: Calculate federal and state income tax

Knowing how much to pay in tax can be a complicated process. Fortunately, there are online calculators out there that can help. FlyFin’s super-accurate 1099 tax calculator was developed with the help of CPAs trained in 1099 taxes to help freelancers enter their details, find all the deductions they qualify for, and get a result they can rely on.

To pay your taxes accurately, it’s important to choose the right tax filing status and understand where you fall in the IRS’ tax brackets, and there are tools to help with that, too.

Step 2: Calculate self-employment taxes

The taxes that freelancers (and every taxpayer) are required to contribute to Social Security and Medicare are called self-employment taxes, or SE taxes. For employees who work for a company, these taxes are known as FICA taxes because they’re part of the Federal Insurance Contributions Act, and they’re split down the middle between the employer and the employee.

But self-employed people are required to pay both portions of self-employment tax. The rate for SECA taxes is 15.3% on net income: 12.4% for Social Security tax and 2.9% for Medicare tax, paid at the end of the year when you file your 1040 form.

Anyone who practices a trade or manages a business as a sole proprietor, independent contractor, LLC, or partnership and earns $400 or more during the tax year is required to pay self-employment taxes. So, that business your cousin has refurbishing and selling guitars makes him self-employed. As a driver for Lyft, your neighbor is self-employed, too. The freelance work your graphic designer friend does on nights and weekends after his ad agency job? Also self-employment work.

As such, all of them are required to pay 15.3% of their net income as SE Tax. But, there is a silver lining. The IRS allows you to deduct half of the 15.3% from your taxable income. You can find out how much you and much you can save with an SE tax calculator.

Step 3: Know how to file taxes in different states

If you live in one state and work in a neighboring state, how you file your taxes depends on a few things. For example, if both states require taxpayers to pay income tax, and they don’t have a reciprocity agreement that allows you to pay tax in just one state, you’ll have to pay tax on what you earn in each state.

You’ll have to file a nonresident return for the state where you work but don’t reside. You’ll need the information from this return, so you can file another tax return in your home state properly. When you file your resident tax return, your home state will usually give you a tax credit in the amount of the tax you paid in another state.

Every state has different tax rules, so make sure to consult a tax expert before preparing your tax return.

Step 4: Choose the best deduction method

When you file your taxes, you’ll want to save the most possible by making the right decision when it comes to standard deductions vs itemiized deductions. This is an important decision because the method you choose can significantly change how much you save.

The standard deduction is a fixed amount that depends on your tax filing status, for example, $19,000 for head of household. But if you claim itemized deductions instead of taking the standard deduction, you will list those deductions on Schedule A of your Form 1040. The total of all your itemized deductions is then subtracted from your taxable income.

Itemized deductions include things like medical expenses, state and local taxes, and charitable donations.

Be aware of all the documents you’ll need to complete your tax filing

When it’s time to file taxes, you can’t lower your tax bill without having the necessary documentation in place. These documents allow you to verify how much you earned and how much you spent on business expenses:

  • 1099 documents
    • 1099-NEC for freelance work payments
    • 1099-MISC for rental and other self-employment income
    • 1099-K for income processed by third-party payment services
    • 1099-DIV for dividends and distributions
    • 1099-INT for interest income
  • Business expenses
    • Bank records can serve as proof – no need for receipts any longer
  • Mileage logs, if you drive for work
  • Records of contributions to charity and retirement plans
  • 1040-ES copies, so you know the estimated tax payments you made
  • 1098 showing your mortgage interest

Consult a CPA who understands 1099 taxes

IRS rules and regulations grow more complex each year, and navigating them to get your taxes done becomes more complicated every time you sit down to fill out the forms. That’s why the help of a certified public accountant, or CPA, is more valuable now than ever before. But accessing the expertise a traditional CPA can provide is easier said than done.

Fortunately, it’s easier than ever to get CPA guidance online with greater affordability and flexibility than ever before. FlyFin’s CPA team specializes in freelancer taxes and is available through the app for unlimited free consultations 24/7 and to file your tax returns, too.

Phew, that was a lot! But we hope you feel more prepared and confident in filing and understanding your freelance taxes moving forward! Good luck this tax season, and as always, we’re rooting for you and your business’ success!

Dealing with Difficult Clients as a Freelancer

Dealing with Difficult Clients as a Freelancer

by | Mar 27, 2023 | Blog, Resources

This is a guest post by Jenny Han, an email marketing expert, writer and editor who loves sharing tips and insight on successful marketing strategies and freelancing.

How to Deal with Challenging Clients

Freelancing can be life-changing (in the best way) for people who value flexibility and independence. Working remotely on a variety projects is a dream come true for many — there’s rarely a cookie-cutter day. But freelancing isn’t all sunshine and rainbows. Like any job, there are unique challenges to overcome, including difficult clients. Below, we’ll explore practical strategies for dealing with tough clients and maintaining balanced working relationships.

1. Set clear deliverables

Clear communication is key, especially with boundary-pushers. Aligning on realistic expectations early on — from the scope of work to your deadlines — can help you avoid conflict and misunderstandings. From the beginning of the project, ensure that you’re on the same page, and then get it in writing.  Including the agreed-upon terms in your proposal and contract will safeguard you in the event of any disputes.

2. Identify and communicate problems as soon as possible

In an ideal client relationship, everything would go according to plan and both parties would be thrilled with the results. But it rarely goes that smoothly. Life happens. Mistakes are made. Barriers and delays creep up on us. We might miss a deadline or deliver work we’re not proud of. It’s important to communicate these issues with your clients as soon as possible to avoid more complications, especially if they’re challenging to work with. Whether the problem is your fault or not doesn’t matter — the focus should be on getting the project back on track. By flagging issues early, you can work together to find a solution.

“Never sit on information that is pertinent to the job. If an issue arises, whether it is your fault or not, you absolutely must flag it with the client at the earliest stage possible. Keeping the client in the dark never ends well, and will make their disappointment worse later on down the line,” warns Brigitte Sterling, an HR Manager at Essay Service and Assignment Help.

3. Maintain regular communication

Good communication is crucial in any relationship, including the client-freelancer dynamic. On top of notifying the client when problems arise, freelancers should also provide regular updates on the project’s progress. Over-communicating is better than under-communicating, and it helps build trust when you’re transparent and consistent. Regular updates keep you and your client tuned into the project’s current state, requirements, and timelines. And, it gives you the chance to ask for the support you need in order to meet your deadlines. Written records of communication can be beneficial if disagreements crop up in the future too — you’ve got a paper trail to reference.

4. Reassure the client

Sometimes external factors like pressure, anxiety, and inexperience are the true culprits in a freelancer-client relationship. If your contact is under a lot of pressure, that can easily get passed along to you like a hot potato. It can be helpful for your own peace of mind to consider the potential reasons why a client is being difficult instead of jumping to conclusions. It not only de-personalizes it, but it helps you approach them with more empathy, which typically leads to better outcomes. You may need to provide more support and hand-holding to these clients to alleviate their fears and build trust.

“I know a lot of freelancers who object to being asked a lot of questions and dislike having to provide constant status updates. My advice to them is always the same: ‘Do what the client wants or give what the client needs to get the job done the way they want it.’ This isn’t about you, it’s about them, and understanding that will make you a better freelancer in the process,” recommends Troy Chase, a Freelance Writer at UKTopWriters and PhD Thesis Writing.

5. Don’t be afraid to walk away

It’s rare for freelancers to start a project with the intention of quitting halfway. However, in some cases, it may be the best  move for both parties. If the client’s behavior becomes intolerable, freelancers should communicate that continued behavior will result in the termination of the project. (It’s also a good idea to have a pre-determined notice period written into the contract.)

You may first want to have an open conversation with the client to see if you can find a middle ground that works for both parties. If you’re not able to compromise and the situation becomes toxic, it’s time to move on.

Walking away from a project can be a difficult choice, especially if you rely on the income, but it can also be a valuable lesson. You learn how to identify red flags earlier on in the client selection process. Plus, you get a real-life opportunity to hone your communication and project management skills.

Most clients are respectful and appreciative of their freelancers, and while these harmonious relationships are wonderful and supportive, they rarely teach us as much as the challenging ones. Tough projects can help you develop resilience and confidence. They can also strengthen your boundaries and inspire you to advocate for yourself in your professional and personal relationships.

In the end, it’s important to remember that the vast majority of clients are respectful and kind. But freelancing comes with its own set of challenges, including dealing with the difficult ones. By learning from your experiences and approaching them with a positive mindset, you can grow tremendously over time.