The Freelancing Comeback: A 10-Step Plan for Women Returning to Work Post-Sabbatical

Deciding If Freelancing Is Right For You

Freelancing offers many potential benefits compared to traditional employment, but it also comes with challenges. As you consider reentering the workforce, take time to reflect on whether freelancing aligns with your interests, skills, lifestyle needs, and desired work-life balance.

Pros of Freelancing

• Flexibility to set your hours and work location
• Ability to choose projects you’re passionate about
• More control over your income and career path
• No office politics or corporate bureaucracy

Cons of Freelancing

• Irregular income and lack of benefits like health insurance
• Need to spend time on non-billable tasks like marketing yourself
• Potentially unpredictable workflow and financial instability
• Lack of structure and community of a traditional workplace

Assessing Your Needs and Skills

Think about your ideal work arrangements in terms of schedule, work location, project diversity, income needs, and work-life balance. Consider your existing skills and experience. Identify any gaps that may require further development before freelancing.

For example, do you have expertise in your chosen field but need to strengthen your project management, marketing, networking, financial planning, and productivity skills to thrive as a freelancer? Be realistic about the time investment required.

Envisioning Your Lifestyle as a Freelancer

Imagine what a typical week of freelancing could look like for you. Would the flexible schedule and autonomy allow you to better support your lifestyle? Or do you value the structure and social connections of an office environment?

Consider practical factors like childcare needs and your ability to work productively at home. Run through scenarios of fluctuating income and irregular workloads. Ensure freelancing aligns with your personal and financial goals before making the leap.

Building Your Freelancing Skillset

When reentering the workforce as a freelancer after a sabbatical, it’s important to identify and build up the key skills you’ll need to succeed. Start by taking an inventory of your past professional experience and identifying transferable skills that are relevant to freelancing. For example, skills like communication, time management, multitasking, problem-solving, and organization are valuable in any work arrangement.

Next, research the types of freelance jobs you’re interested in pursuing and determine if there are additional skills you should learn or improve. Many freelancers invest time in building skills like writing, graphic design, web development, digital marketing, and more based on their freelance niche. Consider taking online courses, watching tutorial videos, reading books and blogs, or joining communities of practice to expand your knowledge. Gaining mastery in specialized, in-demand skills can help attract clients and enable you to command higher rates.

Finally, explore professional certifications that could give you a competitive edge. For example, freelance writers can get certified in SEO, project managers can get certified in popular methodologies like Agile or PMP, and designers can get certified in leading design or photo editing tools. The right credentials can go a long way in instilling client confidence. Continuously developing your skills as a lifelong learner is key to sustainable success as a freelancer.

Creating Your Personal Brand

Your brand is your reputation, image, and identity as a freelancer. It’s how potential clients perceive you and makes you stand out from competitors. When reentering the workforce, focus on defining your niche, ideal clients, and crafting your story and unique value proposition.

Define Your Niche and Ideal Clients

• Consider what services you want to offer. Choose an area you have expertise and interest in.
• Research the target market, competitors and industry trends. Identify gaps you can fill.
• Create an ideal client profile based on demographics, needs and pain points.
• Position yourself as an expert in your niche with a focused brand identity.

Craft Your Story and Unique Value Proposition

• Determine the key strengths, skills and experience you bring to clients.
• Reflect on your background, passions, values and purpose as a freelancer.
• Develop your origin story and what makes your approach special. Communicate why clients should work with you.
• Summarize your unique value proposition – the differentiation you provide over competitors.

Design Your Brand Assets

• Create a logo and tagline that reflects your brand identity and niche.
• Build a website showcasing your services, work samples and value proposition.
• Produce business cards, email signatures,s and templates with consistent branding.
• Curate social media profiles to highlight your expertise and personality.

With a defined personal brand, you can establish credibility, connect with ideal clients, and communicate the value you offer as a freelancer.

Setting Your Rates

One of the most important steps when starting out as a freelancer is determining how much to charge for your services. With no previous clients or reviews, it can be tempting to undervalue your work, but pricing too low can undermine your perceived expertise. At the same time, you don’t want to overprice yourself compared to industry standards.

Do thorough research on typical rates in your field and area of expertise. Look at job postings to see what clients are willing to pay. Check industry reports like those from the Bureau of Labor Statistics. Search profiles of freelancers similar to you on freelancing sites like Upwork and Fiverr to find common pricing tiers.

In general, more experienced freelancers can demand higher rates. However, newer freelancers shouldn’t undersell themselves either. Take into account your unique skills, education, credentials, and the value you provide. Consider specializing in higher paying niche skills. Recognize that some skills are simply more in demand.

When first starting out, an hourly rate structure may provide more flexibility. You can adjust the number of hours as you become more efficient. Hourly also simplifies tracking time for tax purposes. However, project-based pricing becomes preferable as you establish your expertise. Estimate the number of hours required and provide a fixed project quote. This transfers time management risk to you, but allows capping maximum hours.

Reevaluate your rates every 6-12 months as you gain experience, reviews, and proficiency. Never be afraid to raise prices for stellar services. But keep rates modest until established. With smart pricing, you can build a steady freelance income after your sabbatical.

Finding Freelance Job Opportunities

When starting out as a freelancer, finding your first clients can be challenging. However, there are several effective strategies to tap into new opportunities:

Leverage Your Networks and Referrals

Don’t underestimate the power of tapping into your existing networks! Let friends, family, colleagues, and acquaintances know that you are taking on freelance work. They can connect you with potential clients or provide referrals. Attend industry events and network to meet new contacts. A personal referral goes a long way in landing your first freelance gigs.

Join Freelance Job Sites

Online freelance job platforms like Upwork, Fiverr, and Freelancer can be great places to find your first freelance clients. Create a strong profile highlighting your skills and experience. Bid competitively on projects to get those initial 5-star reviews. As you build your reputation, you’ll start receiving invitations for higher-paying, long-term projects.

Attend Networking Events

Look for local networking meetups, conferences, and industry events to connect face-to-face with potential clients. Come prepared with business cards and an elevator pitch. Share that you’re taking on freelance work and looking for new projects. Events focused on entrepreneurs, startups, freelancing, and your particular industry can be great for meeting prospective clients.

The key is casting a wide net through both your existing networks and new connections. Tell everyone that you’re open for business. With persistence and by delivering great work, you’ll secure those critical first freelance jobs to build up your portfolio and client base.

Building Your Portfolio

Your portfolio is one of the most important elements for landing freelance jobs. It allows you to showcase your skills and experience to potential clients. Here are some tips for building a strong portfolio as a freelancer:

Curate Examples of Past Work

• Gather examples of your best work from previous jobs or clients. This could include writing samples, design projects, photos of artwork, etc. Make sure you have permission to use these pieces.
• Organize your work samples neatly into categories or showcase different skills.
• Only include your strongest pieces that demonstrate your abilities. Quality over quantity.

Create Sample Projects

• If you have gaps in your portfolio, create mock projects or samples that highlight your expertise. These could be blog posts, logo designs, financial plans, etc.
• Come up with realistic examples that are specific to the type of freelance work you want to do.
• Ask friends/colleagues to provide sample projects/problems for you to solve. This creates real-world examples for your portfolio.

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Get Testimonials From Past Clients

• Reach out to past employers and clients and ask if they’d be willing to provide a testimonial.
• Testimonials should highlight specific skills, positive experiences working with you, and reasons they’d recommend you.
• Include a mix of testimonials from different roles to show well-rounded abilities.
• Display testimonials prominently on your website or portfolio. They help build trust and credibility.

Managing Your Finances

Transitioning to freelance work means your income likely won’t be as stable or predictable as a regular paycheck. Here are some financial considerations as you reenter the workforce as a freelancer:

Set Up Systems For Invoicing, Taxes, and Records

• Obtain an Employer Identification Number (EIN) from the IRS if working as a sole proprietor. This establishes you as a business entity for tax purposes.
• Set up an invoicing system to bill clients and get paid. Free tools like Wave or Freshbooks make invoicing easy. Send clients clear invoices and follow up on overdue payments.
• Consult an accountant about quarterly estimated income tax payments you may need to make as a freelancer. An accountant can also advise on business deductions you can take.
• Track income and expenses carefully. Retain receipts and records in case of an IRS audit. Consider using accounting software to simplify record-keeping.

Budget and Manage Irregular Income

• Create a budget to understand your basic monthly living expenses. As a freelancer, your income may fluctuate. Budget to build savings so you have a cushion in slower months.
• Try to maintain 3-6 months’ worth of living expenses in an emergency fund. Don’t rely on a predictable biweekly paycheck.
• During busy, high-earning times, set aside portions of income for the slower periods. Look for ways to reduce expenses if work is slow.
• Arrange access to liquid funds like a line of credit as a safety net for income volatility. Avoid racking up high-interest credit card debt.

Get Healthcare and Insurance

• Research plans on the Health Insurance Marketplace if not covered by a spouse or family member’s plan. Individual plans may be tax deductible for freelancers.
• Look into affordable catastrophic health insurance plans to protect yourself from major medical expenses. Pair this with an HSA or FSA.
• Consider supplemental insurance like disability, life, and liability policies. These provide protection if you’re hurt, sick, or sued.
• Handle your own retirement savings. Freelancers are not eligible for employer-based plans. Open an IRA or solo 401k to save for retirement.
• Track any mileage, equipment, home office, and other business expenses. These are often deductible on your annual tax return, reducing your freelance taxes owed.

Maintaining Work-Life Balance

As a freelancer reentering the workforce after a sabbatical, it’s important to set boundaries and maintain a healthy work-life balance. This will help you avoid burnout.

Set Clear Boundaries with Clients

• Be upfront with clients about your availability and set expectations. Make your working hours clear.
• Don’t feel pressured to be available 24/7. Push back if clients expect immediate responses at all hours.
• Block off time in your schedule for non-work activities. Don’t sacrifice self-care or family time.

Create a Routine and Schedule

• Structure your day with set working hours and break times. Avoid working in a frenzy.
• Plan out your week in advance and block off time for each client project.
• Give yourself set hours to be “off work” where you disconnect and focus on non-work activities.

Watch: WorkLife Balance: A New Perspective

Practice Self-Care to Avoid Burnout

• Make sure to take regular breaks during work to stretch, rest your eyes, or grab a snack.
• Don’t neglect exercise, healthy eating, and proper sleep. Carve out time each week for self-care activities.
• Set aside time for hobbies, friends, and fun. Don’t let work take over your whole life.
• If you start feeling burnt out, take time off and reset. Don’t overwhelm yourself with clients.

By setting healthy boundaries, sticking to a routine, and making self-care a priority, you can avoid burnout as a freelancer. Protect your work-life balance.

Networking and Marketing Yourself

As a freelancer reentering the workforce, networking and marketing yourself effectively is crucial to build your client base and continuously generate new leads. Here are some tips:

Identify Networking Opportunities

• Attend industry events, conferences, meetups, and trade shows in your city. These are great for meeting potential new clients and collaborators face-to-face.
• Look for relevant professional associations and organizations you can join, both in-person and virtual groups. These provide excellent networking amongst your peers.
• Let friends, family, and former colleagues know you are freelancing. They can connect you with people in their networks seeking your services.
• Consider informational interviews to build connections, seek advice, and learn about opportunities.

Consistently Reach Out To New Leads

• Set aside dedicated time each week to find and contact potential new clients. Create a spreadsheet to track your outreach efforts.
• Look for businesses in your area or industry that could use your services. Send customized pitches explaining why you’d be a great fit.
• Follow up with leads consistently, not just once. It often takes multiple touchpoints before converting a lead to a client.
• Offer free samples or discounted initial work to secure those first few clients and build up reviews.

Use Social Media and Content Marketing

• Create a strong social media presence on platforms popular with your target clients. Share examples of your work and industry insights.
• Write blog posts and create portfolio samples that demonstrate your expertise. Optimize them with relevant keywords so they can be found by potential clients searching online.
• Publish helpful content and engage with others consistently on social media and professional forums related to your field. Become a known expert.
• Include links to your website and social profiles when interacting online to drive traffic.
• Use paid ads on platforms like LinkedIn to get your service offerings in front of relevant audiences. Start small to test effectiveness.

Being Productive and Organized as a Freelancer

Freelancing demands working from home, it’s crucial to implement productivity tools, routines, and habits in order to be organized and get work done efficiently. Here are some tips:

Set Up a Functional Home Office

• Dedicate a space in your home as a work-only zone. Avoid working in bed or on the couch, as it’s harder to be productive in leisure spaces.
• Make sure your workspace has strong WiFi connectivity and minimal distractions. Consider a dedicated desk and comfortable office chair.
• Organize your office supplies, computer equipment, files, and paperwork so everything has a place. Declutter frequently.

Use Productivity Tools and Systems

• Apps like Trello, Asana, and Todoist can help you manage tasks and projects. Calendar apps assist with scheduling and time blocking.
• Enable Do Not Disturb on your devices during work hours to avoid unnecessary interruptions.
• Use browser extensions like StayFocusd and LeechBlock to limit time on distracting websites.
• Consider using automated scripts or AI writing tools to help speed up repetitive tasks.

Separate Work and Personal Time

• Define set work hours and stick to them. Avoid the temptation to work too late or constantly check emails after hours.
• Take breaks throughout the day to rest your mind, stretch, and disconnect. Stepping away boosts creativity and energy.
• When you finish for the day, set a clear cutoff time. Shut down your office, devices, and mental work mode.
• Mark work days and off days in your calendar. Give yourself real weekends without work.

Staying organized as a freelancer creates structure and productivity. Implement systems that help you focus on work when needed and unwind when done.