Fully Booked VA Blog

Making the Leap: How to Successfully Navigate a Mid-Career Change to Self-Employment

If you’re considering making a change mid-career to self-employment, you’re not alone. It’s a big consideration, and many people are starting that journey, especially following the “return to work” mandate.

But it’s not easy… We’ve done what we thought we were “supposed” to – we dug in and embarked on careers in the traditional 9-5 model and in most cases, made a commitment for the long term. 

But then… life sets in. We start asking ourselves things like, “Is this really all there is for me?” Unfulfilling, understimulating work; a lack of autonomy and time freedom; and a disconnection with what we’re showing up for every day to support our families results in inevitable mid-career burnout.

So, we begin to acknowledge that voice that’s telling us – there has to be a better, more aligned way to work and live.

Making a mid-career change can be an intimidating prospect, though. Having said that, for those who dream of breaking free from the traditional 9-to-5 career and embarking on the journey of self-employment, it presents an exciting opportunity for personal growth and professional fulfillment. In this article, we’ll explore the key steps to successfully navigating a mid-career change to self-employment and making the leap into entrepreneurship.

We’ll take a closer look at each of these, however, those steps are:

1. Assess your skills and interests

2. Research viable business ideas

3. Develop a business plan

4. Begin to build your brand and online presence

5. Plan your finances

6. Begin part-time

Whether you’ve been in your current career for five years or fifteen, transitioning to self-employment requires careful planning and a strategic approach. And yet, with that planning and strategy, it’s completely achievable for anyone to replace a full-time income with the valid, established model of freelancing and service-based business ownership. 

In that context, we’ll delve into the steps just outlined, including how to assess your skills, identify viable business ideas, and develop a plan to set yourself up for success. Additionally, we’ll share insights on overcoming challenges, managing financial considerations, and building a network to support you throughout your entrepreneurial journey.

If you’ve ever dreaded Monday mornings, or have ever resented spending more time with your career than you do your family or other interests, take heart as we guide you through the process of making a mid-career change to self-employment.

Fully Booked VA List of 275 Services


Assessing your skills and interests: Identifying your strengths and passions

With the right mindset, preparation, and determination, you can pursue your passion, create a thriving and well-paying business, and find fulfillment in your work. Don’t let fear and self-doubt hold you back – instead, embrace the possibilities that come with venturing into self-employment. Your first stop on this journey is to assess what it is you’d truly like to do when it comes to your work.

If that’s unclear to you right now, that’s okay. Part of this process is taking inventory of where you’ve been and currently are so that you can cast a greater vision for your career and financial future.

To be clear, the optimal path for new freelancers making a mid-career change is to get started with the skills and experience you already have. This contributes to the “simple transition” out of being an in-house employee to continuing to work – but for yourself, and completely on your own terms.

Getting started with skills you already have is also a way to decrease your learning curve, begin earning income quickly, and create momentum in your new service-based business.

Before embarking on a mid-career change to self-employment, it’s valuable to assess your skills and interests. This will help you not only identify what kind of services you can begin offering immediately, but also what potentially more stimulating and interesting areas you’d like to pursue in the future as you’re growing and scaling your business.

Your strengths and passions will be a good guidepost for your new venture and will help ensure that you’re creating a business you enjoy, versus continuing to “just show up” for work that isn’t fulfilling or meaningful for you.

When it comes to choosing services to get started with, consider the skills you’ve acquired throughout your career and how they can be leveraged in a new business. Additionally, think about the activities or tasks that bring you joy and fulfillment.

Identifying your strengths and passions will help you align your self-employment journey with what truly matters to you. It’s time and thought well spent, and good material to recall later as you’re in the process of growing your business.

Mid-career change to self-employment: Making the transition successfully.

Researching self-employment opportunities: Exploring different industries and business models

Once you’ve identified your skills and interests, explore how they can be applied in a self-employment setting. It may feel challenging, at first, to identify how your current skills can translate into freelance services, however, if you’ve had any work experience at all (or even home-management experience) you absolutely have at least one skill, right now, that other business owners need.

This list of 275+ Services workbook can help you identify some of those.

As you’re casting a vision for an ideal business, you can also consider things like whether there are any gaps in the market that you can fill with your expertise. Research different industries and business models that align with your skills and interests. This exploration phase will help you identify viable self-employment opportunities that have the potential to be both personally fulfilling and financially rewarding.

The most important thing to note in this stage of your journey is to not get stuck here in the “research phase.” While it can be exciting to start exploring and considering the possibilities, it can often become a way of subconsciously procrastinating or avoiding taking action. Remember – you have the skills you need to begin earning income independently right now.

When it comes to clarifying and growing your business, it’s an ever-evolving process and you’ll be continuously gathering information about what you enjoy, what works, what doesn’t work, etc. It’s all just information and there’s always an opportunity to adjust accordingly – nothing is set in stone in your freelance business. But, it’s information you won’t have until you get into motion and actually find out.

Developing a business plan: Setting goals, identifying target market, and creating a marketing strategy

Once you’ve identified an idea of where you can get started with your services and where you may like to head in the future with your business, it’s time to develop a business plan. This plan will serve as a roadmap for your self-employment journey and provide clarity on how to achieve your goals. Start by setting clear and measurable objectives for your business. What do you hope to achieve in the short term and long term? Setting goals will help you stay focused and motivated throughout the transition.

In addition to setting goals, it’s valuable to identify your target market. Who are your ideal clients? What are their needs and pain points? Understanding your target market will help you find those initial clients more quickly. When you know who you’re looking for, it’s easier to locate and connect with them.

Once you have a clear understanding of your target market, develop a marketing strategy to reach and engage with those prospects. Inside our flagship freelance business training course, VA Foundations, we teach various methods for doing this when you’re just getting started. The most accessible, simple way initially is through social media. This is by no means the only way, but it is a quick and effective way to initially establish an online presence with a profile or profiles dedicated to your business.

This is another stop in your journey to making your ideal, best mid-career change however it’s also another place to avoid getting overwhelmed or even worse – stuck. The phrase “marketing strategy” can feel intimidating, but it’s really just a way to identify how you’ll present yourself to the marketplace and connect with quality clients.

As you progress in your business, you may consider more “long game” strategies, like content marketing, or email marketing. Again, there are a variety of ways to let people know about your business and what’s most valuable is to pick a method (or methods) that resonates with you and that you can follow through with consistently.

With time, experience, and information, a well-defined marketing strategy will help you attract and retain customers as you transition to full-time self-employment.

Making the leap: How to successfully navigate a mid-career change to self-employment

Building your personal brand: Establishing an online presence and networking

As your business develops, it’s an energizing undertaking to create a compelling brand message that resonates with your target market and differentiates you from competitors. This business is you. People engage with people, not services, or titles, or websites. Your brand is your unique opportunity to communicate to the marketplace what values you hold and who you are in your business.

Particularly in today’s digital age when we’re craving human connection, building a strong personal brand is essential for self-employed professionals. Establishing an online presence will help you showcase your expertise, connect with potential clients, and build credibility in your chosen industry. 

Again, there are a variety of ways to do this simply and fairly quickly as you’re starting your service-based business, like creating a dedicated LinkedIn profile, a one-page resume PDF, or a simple services page (which you can also do on LinkedIn).

As you progress in your business, creating a professional website that highlights your skills, experience, and offerings is a way to further establish and legitimize your online presence. It is not necessary to have a website to get started by any means, and we don’t recommend focusing on this task initially. 

Why? Because it’s too easy to get hung up here and wait several months before your website is “just right” before getting started.

When it comes to leveraging social media platforms to develop your personal brand, choose the platforms that align with your target market and industry. If you’re interested in health and wellness, for example, Instagram would be an ideal platform. If your background is in personal finance, LinkedIn would be a more appropriate choice. 

Engage with your audience by sharing valuable content, participating in industry discussions, and showcasing your expertise. It’s important to “show up” on social media with an attitude of authenticity and service, versus being “on the hunt” for clients.

Have conversations. Connect. Develop relationships. This is how the best networking opportunities are nurtured, and with time and consistency, the outcome can be very fruitful.

Aside from social media, other kinds of networking are also valuable for self-employed professionals. Attend industry events, join online communities, and seek mentorship from experienced entrepreneurs. Building a strong network will provide support, guidance, and potential business opportunities throughout your self-employment journey.

Lastly, keep in mind that the best working relationships don’t come from some convoluted, fancy marketing strategy. They come from simply having conversations.

Financial considerations: Budgeting, saving, and managing cash flow during the transition

Transitioning from employment to self-employment often involves financial adjustments. It’s essential to prepare for this transition by carefully and intentionally managing your finances. Start by creating a budget that takes into account your current expenses and ideal, projected income as a self-employed professional.

As you’re looking to replace a full-time income from your former career, keep in mind that you’ll now be responsible for things like health insurance and self-employment taxes (depending on your region). For that reason, we recommend setting your service rates 25% higher than your current income rate to cover those kinds of costs.

During the transition period, it’s crucial to have a financial buffer to cover any unexpected expenses or income fluctuations. Identify areas where you can streamline and save money to ensure a smooth transition and consider saving a portion of your income while you’re still employed to build a financial safety net.

Managing your cash flow effectively will help you navigate the financial challenges that may arise during the mid-career change to self-employment.

Making the leap: How to successfully navigate a mid-career change to self-employment

Overcoming common obstacles: Dealing with fear, uncertainty, and self-doubt

Making a mid-career change to self-employment can be (and often is) accompanied by fear, uncertainty, and self-doubt. It’s important to acknowledge these emotions, accept that they’re a reality and are just part of this, and develop strategies to overcome them.

Surround yourself with a positive support system that believes in your abilities and aspirations. Seek guidance from mentors or coaches who have successfully transitioned to self-employment. Avoid conversations with well-meaning but misinformed friends and family who ask you things like, “When are you going back to work?”

Surrounding yourself with the right support and energy during this process can provide valuable insight and help you navigate challenges along the way.

In addition to seeking support, focus on building resilience and developing a growth mindset. Embrace failure as an opportunity for learning and growth – because there really is no “failure” in this. It’s all just information, remember? 

When we can adopt an attitude of curiosity versus judgment about our efforts, it’s a far more productive and healthy place to grow from versus the cycle of anxiety and beating ourselves up because something didn’t work exactly as we’d hoped.

Celebrate small wins and milestones to stay motivated. Even better, share them with a community or group of supportive, like-minded individuals like the one you’ll find inside Fully Booked VA. Remember that the journey to self-employment isn’t always smooth, but it can lead to personal and professional fulfillment beyond anything you can imagine right now. In this venture, it’s not as much about the “results” you achieve, but rather who you become in the process.

Taking the leap: Steps to smoothly transition from employment to self-employment

Once you’ve assessed your skills, started formulating a business plan, considered the personal brand you’d like to develop, and have begun to establish a support network, it’s time to take the leap and transition from employment to self-employment. Start by creating a detailed transition plan that outlines the steps you need to take to make the switch. This plan should include a timeline, action items, and contingency plans.

Consider starting your self-employment journey as a side hustle while you’re still employed so you can build up your business with the safety net of your current income. While this may sound daunting at first, it’s completely achievable and has been accomplished by countless numbers of our members inside Fully Booked VA.

Working within this safety net allows you to test the viability of your business ideas and build a customer base before leaving your full-time career. As your self-employment venture gains momentum, if possible, gradually reduce your hours at your current job until you are ready to make the leap full-time.

Keep in mind that transitioning to self-employment requires patience, perseverance, and adaptability. But, it’s also incredibly energizing and motivating to say goodbye to the mid-career slump – permanently.

Embracing the challenges and opportunities of a mid-career change to self-employment can lead to a fulfilling and rewarding professional journey. Remember to manage your finances effectively, overcome obstacles, and take calculated risks. 

With the right mindset, preparation, and determination, you can make the leap into self-employment and create a thriving business that brings you joy and fulfillment. Don’t let fear hold you back; instead, embrace the possibilities that come with venturing into being a freelancer.

We know, making a mid-career change to self-employment can be daunting. Fear, uncertainty, and self-doubt often creep in when contemplating leaving the stability of a regular paycheck and venturing into the unknown. However, these obstacles can be overcome with the right mindset and strategies.

1. Acknowledge and confront your fears

It’s natural to have fears when embarking on a mid-career change. Identify the specific fears that are holding you back, confront them head-on, and most importantly move through them. Remember that these are thoughts and beliefs – not necessarily truths. 

You get to write this story. Develop a plan to address fear when it arises, because it will resurface as you continue to grow professionally and personally.

2. Take calculated risks

Transitioning to self-employment involves taking risks, but it doesn’t mean you have to jump blindly. Conduct thorough research (but don’t get stuck here), gather information, and make informed decisions. By taking calculated risks, you can minimize uncertainty and increase your chances of success.

3. Develop a growth mindset

Cultivate a growth mindset that embraces challenges and views failures as learning opportunities – because that’s exactly what they are. Understand that setbacks are a part of the journey and can help you grow both personally and professionally. Stay adaptable, open-minded, and willing to learn from your experiences.

Fully Booked VA List of 275 Services


Conclusion: Embracing the challenges and opportunities of a mid-career change

Transitioning from employment to self-employment requires careful planning and strategic execution. To summarize where we’ve been so far, follow these steps to set yourself up for your best mid-career job change.

1. Assess your skills and interests

Identify your strengths, transferable skills, and areas of interest. Reflect on what you enjoy doing and what you are passionate about. This self-assessment will help you align your career change with your passions and increase your chances of long-term success.

2. Research viable business ideas

Explore various business ideas that align with your skills, interests, and market demand. Conduct some research to identify potential customers and trends. Think about the feasibility and profitability of your ideas to both narrow down your options and ensure you’re creating something you’ll enjoy and are fulfilled by.

3. Develop a business plan

Create a simple business plan (one page is fine, and some have even been written on paper napkins, although we don’t recommend that!) that outlines your goals, target market, marketing strategies, financial projections, and operational plans. A thoughtfully crafted business plan will serve as a roadmap to guide you through the initial stages of your self-employment journey.

If you need guidance and direction with this step, a simple Google search for “one-page business plan” can inspire some ideas.

4. Build your brand and online presence

Begin to formulate a strong personal brand and create an online presence to attract clients and showcase your expertise. In the future, it’s valuable to develop a professional website (but not necessary for getting started). It’s initially quicker and simpler to optimize your social media profiles where you can share valuable and relevant content in your niche and develop your network.

A longer-term digital marketing strategy can help you expand your reach and attract potential customers in the future.

5. Plan your finances

Carefully analyze your financial situation and plan for the financial challenges that may arise during the transition period. Create a budget, save an emergency fund, and consider seeking financial advice to ensure your financial stability as you make the leap to self-employment.

6. Begin part-time

Consider starting your self-employment journey on a part-time basis. This allows you to test the waters, gain experience, and build a client base while still having a steady income from your current job. As your self-employment venture grows, you can gradually transition to full-time entrepreneurship.

Again, making a mid-career switch is achievable for anyone with the right information and mindset. These last few years have taught us that there truly is a better way to work and live, including the increasing numbers of businesses that are contracting out for services versus hiring in-house employees. It’s a model that just makes sense and is anything but new.

Rather, the current climate of our economy and world workforce have brought freelancing to the forefront as an established, proven model for earning income. When you consider the advantages of complete autonomy and limitless potential for service providers, and the extensive cost-savings for businesses who hire freelancers, it’s truly a win-win scenario.

The question is quickly becoming less, should I honor this voice that’s telling me there has to be more than this and make a mid-career job change… and more, how can I make the best mid-career change for my unique goals, desires, and circumstances?

After all, why not you? Why not now?

If you’re ready to take your next, actionable step in your career journey, enroll in VA Foundations for everything you need to start, build, and scale a successful, long-term service-based business

Laura Nicholls


Laura manages the VA Leads Community, the blog and does a ton of other things for Horkey HandBook behind the curtain! She’s also an alum of both 30 Days or Less courses (VA and freelance writing!). She started off as a writer and branched out into building her VA business focusing on executive management and content creation. Laura is in love with her life in Northern California taking care of horses and being full-time single mom to her daughter.

Not sure which services to offer as a Virtual Assistant?

Enter your email and we’ll send you a full list of what you can sell, how valuable those skills are and where to find clients to serve!