The Freelance Shift

Jennifer F
  • 0.0 (0)
  • Entrepreneurship
  • Updated Semiweekly

Welcome to The Freelance Shift. I’m Jennifer, and I help freelancers simplify their tools and workflows so they can work less, earn more, and avoid burnout. This is your go-to space for practical, real-world freelancing—covering clients, pricing, systems, and the simple tech that actually makes your business easier to run. If you’re tired of feeling overworked and disorganized, you’re in the right place. Each week, I’ll share clear, actionable strategies to help you work smarter, stay organized, and build a freelance business that actually works for you. Follow along for weekly tips.

  1. 2h ago

    Be Your Own Freelance Benefits Department (Ep 136)

    How do you save for retirement, cover healthcare costs, and handle unpredictable income as a freelancer? In this video, I explain four accounts that can help: a Health Savings Account (HSA), a personal IRA, a SEP IRA, and a high-yield savings account.I’m sharing how these accounts fit into my financial setup—and how I’m balancing retirement savings with paying college tuition for my two daughters.We’ll cover:• What each account is and how freelancers and solopreneurs can use it• HSA healthcare expenses, reimbursement, and withdrawal rules after age 65• The differences between personal IRAs and SEP IRAs• Using a high-yield savings account for an emergency fund and cash flow cushion• Making financial decisions when family priorities compete for the same moneyReading Add a Zero by Rose Han encouraged me to rethink how I organize my freelance income. Here’s what I changed—and what I’m still figuring out.What two financial priorities are hardest for you to balance? Share in the comments.Subscribe to The Freelance Shift for practical conversations about freelancing, self-employment, and building a business that supports your life.This video shares my personal experience and opinions, not individualized financial, investment, or tax advice. U.S. account rules and eligibility vary.#FreelancerFinances #SelfEmployed #RetirementPlanningThe Freelance ShiftBe Your Own Freelance Benefits Department (Ep 136)https://thefreelanceshift.com

  2. 4d ago

    How I Handle Health Insurance as a Freelancer (Ep 135)

    Related video: Health Insurance for Freelancers: My Experience & Sticker Shockhttps://youtu.be/Kg-I0ltntcYAlmost $1,000 a month for health insurance—and the pharmacy still asked, “Do you have another insurance?”I’m Jennifer from The Freelance Shift. Losing employer-sponsored health insurance was one of the scariest parts of leaving my professor job. Now, Blue Cross is discontinuing my PPO option for 2027 and moving me to an HMO.In this video, I share what I’m paying for coverage just for myself, why my income makes me ineligible for a federal premium subsidy, and the options I’m considering. My children are covered through my ex-husband’s insurance.I also explain what I recently learned about GoodRx, how its prescription coupons can sometimes cost less than using insurance, and the deductible tradeoff to check.I’m not an insurance specialist. This is my personal experience, and I’m still thinking through my decision.Have you switched from a PPO to an HMO? How do you handle health insurance as a freelancer? Share your experience and suggestions in the comments.Official resources:• Self-employed coverage: https://www.healthcare.gov/self-employed/• Enrollment dates: https://www.healthcare.gov/quick-guide/dates-and-deadlines/• Plan types: https://www.healthcare.gov/choose-a-plan/plan-types/• Federal subsidy eligibility: https://www.irs.gov/credits-deductions/premium-tax-credit-ptc-overview• Prescription price comparisons: https://www.goodrx.com/#FreelanceShift #FreelancerLife #HealthInsuranceThe Freelance ShiftHow I Handle Health Insurance as a Freelancer (Ep 135)https://thefreelanceshift.com

  3. 6d ago

    AI Evaluator Assessment? Don’t Click START Until You Watch This (Ep 135)

    Related videos: Should Freelancers Try AI Evaluation Jobs My Honest Experience (Ep 116)https://youtu.be/fLMgGTbdkcIPreparing for an AI evaluator assessment? Before you click “Start,” learn how to read prompts carefully, compare AI responses, and explain your ratings clearly.I’m Jennifer from The Freelance Shift. In this video, I share practical preparation tips and what I wish I’d known—including why polished answers aren’t always good answers, how to write specific explanations, and what to check before starting timed tasks.You’ll learn:• How to spot missed instructions and requirements• How to evaluate natural, understandable language• How to explain similar observations without repeating yourself• Why attention to detail and following directions matter• A simple practice exercise to build your evaluation skillsAssessment requirements vary by company and role, so always follow your platform’s instructions. Preparation doesn’t guarantee a pass, but it can help you approach the assessment with greater confidence.Which skill would you like to practice most: spotting mistakes, comparing responses, or explaining your ratings? Share below—without posting actual assessment questions.Subscribe to The Freelance Shift for practical advice on freelancing, AI work, and building a profitable business.#AIEvaluator #AIAssessment #Freelancing

  4. Oct 15

    The Career Alternative Most Professionals Overlook (Ep 134)

    Related articles and videos: What I Learned Building a Fractional Executive Careerhttps://www.fastcompany.com/91507342/what-i-learned-building-a-fractional-executive-careerA Day in the Life SeriesMonday: https://youtu.be/X9QUAuC-RzATuesday: https://youtu.be/KTBeAaNFpTYWednesday: https://youtu.be/zYRD9oaIV8IThursday: https://youtu.be/83JRN1jKIIoFriday: https://youtu.be/hEotaqKcPcoWhat if the best next step in your career isn't finding a better job—but working for multiple companies instead?I'm currently working with 7 different clients, and I've discovered something that many experienced professionals overlook: you don't have to depend on one employer to build a successful, rewarding career.More companies are turning to fractional professionals, freelancers, contractors, and consultants to access experienced talent without hiring full-time employees. And this could create opportunities for people who already have valuable professional skills.In this video, I share how I've built my freelance business around multiple clients, why this approach can give you more control over your income, and what you need to know about the growing world of fractional work.Inspired by a Fast Company article about building a fractional executive career, I'll also share practical strategies for finding opportunities that may never appear under the title "freelance."You may already have the skills companies need. You just need to know where to look.Subscribe to The Freelance Shift for practical freelancing strategies, AI tools, and real-world insights into building a profitable independent business.#Freelancing #FractionalWork #CareerChange #FreelanceBusiness #ConsultingThe Freelance ShiftThe Career Alternative Most Professionals Overlook (Ep 134)https://thefreelanceshift.com

  5. Oct 13

    Why More Professionals Are Choosing Freelancing (Ep 133)

    The freelance economy is booming—but are experienced professionals missing out on one of the biggest career opportunities?xI recently came across an Inc. magazine article, "The Freelance Economy Is Booming Right Now," and it got me thinking about why more professionals are choosing to build their own freelance businesses instead of relying on traditional employment.After more than 20 years in education, training, and instructional design, I've built a freelance business working with multiple clients in consulting, training, and AI. And one of the biggest lessons I've learned is that you don't have to start over to become a successful freelancer.In this video, I share four reasons professional freelancing is becoming more attractive, how it can give you greater control over your career and earning potential, and why your existing experience may be your greatest advantage.Whether you're considering freelancing after 40, exploring independent consulting, or looking for ways to earn more using skills you already have, this video will help you see what's possible.📰 Read the Inc. article that inspired this video:https://www.inc.com/brian-honigman/the-freelance-economy-is-booming-right-now/91302893Subscribe to The Freelance Shift for practical strategies, AI tools, and real-world advice on building a profitable freelance business.#Freelancing #FreelanceBusiness #CareerChange #FreelancingAfter40 #IndependentConsultantThe Freelance Shift Why More Professionals Are Choosing Freelancing (Ep 133)https://thefreelanceshift.com

  6. Oct 8

    I Asked Copilot to Find the Risks in My Project Plan (Ep 132)

    Related content to watch next: How I Use Copilot to Build a Project Plan in Minutes (Ep 102)https://youtu.be/NvwywOqk2rMTurn Meeting Notes Into a Project Plan With Copilot (Ep 131)https://youtu.be/qVMt8iRHi2MWhat if your project plan has problems you haven't noticed yet? Can Microsoft Copilot help you catch them before they turn into missed deadlines, delays, or unhappy clients?In this video, I use Copilot to analyze a real project plan for potential risks, unrealistic deadlines, missing tasks, resource conflicts, and bottlenecks. I'll share the exact AI prompts I use to identify problems, evaluate dependencies, create a risk register, and uncover questions I should ask my client before a project begins.Whether you're a freelancer, consultant, project manager, or business professional, discover how to use Microsoft Copilot for project management to work smarter, reduce administrative work, and make better decisions.Subscribe to The Freelance Shift for practical AI tutorials, productivity strategies, and tips for building a profitable freelance business.#MicrosoftCopilot #ProjectManagement #AIProductivity #FreelancingThe Freelance ShiftI Asked Copilot to Find the Risks in My Project Plan (Ep 132)https://thefreelanceshift.com

  7. Oct 6

    Turn Meeting Notes Into a Project Plan With Copilot (Ep 131)

    Turn messy meeting notes into a structured project plan with Microsoft Copilot in minutes.In this video, I show you how I use Copilot to pull action items, owners, deadlines, dependencies, and missing information from ordinary meeting notes and turn them into a project plan you can actually use. I’ll also share the Copilot prompts I use to identify gaps, organize the work, and create a follow-up for the project team.If you’re a freelancer, consultant, project manager, or anyone trying to use AI to get real work done, this is a practical workflow you can use after your next meeting.**In this video:**- Turn meeting notes into action items- Build a project plan with Copilot- Identify missing tasks and information- Organize the plan in Excel- Create a client or team follow-upSubscribe to The Freelance Shift for practical ways to use AI, work more efficiently, and build a profitable freelance business.**#MicrosoftCopilot #Copilot #ProjectManagement #AIProductivity #Freelancing #Excel**The Freelance ShiftTurn Meeting Notes Into a Project Plan With Copilot (Ep 131)https://thefreelanceshift.com

  8. Oct 1

    AI Jobs Aren’t Just for Tech People (Ep 130)

    Think AI jobs are only for programmers and tech experts? Think again.My background is in education, curriculum development, instructional design, training, and evaluation—and those skills have helped me find opportunities working with AI.In this video, I share how professionals from education, healthcare, finance, writing, science, marketing, and other fields may be able to use the expertise they already have in AI evaluation and other AI-related freelance work.You may not need to become an AI expert. Your existing expertise could be exactly what these companies need.Subscribe to The Freelance Shift for real-world strategies for finding freelance opportunities, using AI, and building a profitable freelance business. The Freelance Shift AI Jobs Aren’t Just for Tech People (Ep 130) https://thefreelanceshift.com

See All (57)

About

Welcome to The Freelance Shift. I’m Jennifer, and I help freelancers simplify their tools and workflows so they can work less, earn more, and avoid burnout. This is your go-to space for practical, real-world freelancing—covering clients, pricing, systems, and the simple tech that actually makes your business easier to run. If you’re tired of feeling overworked and disorganized, you’re in the right place. Each week, I’ll share clear, actionable strategies to help you work smarter, stay organized, and build a freelance business that actually works for you. Follow along for weekly tips.

Information

  • Creator
    Jennifer F
  • Years Active
    2026
  • Episodes
    57
  • Rating
    Clean
  • Copyright
    © Jennifer F
  • Show Website
    The Freelance Shift