October 20, 2023

Taking the Leap: Your Guide to Going Self-Employed and Thriving

Business Tips

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I’m an executive coach and accomplished business consultant who brings experience as a two-time start-up Chief Operating Officer, small business and entrepreneurial expert, and coach to my work. Learn more about me here!

Meet Brandi Keiser

Well, hello there, goal-getter!

Are you ready to take the plunge into the world of self-employment? If you’re itching to break free from the 9-to-5 grind and carve your own path, you’re not alone. I have been there myself and am here to guide you through transitioning from a corporate job to becoming a successful self-employed individual.

1. Self-Reflection and Goal Setting

Before you hand in your two-week notice, it’s essential to engage in some serious self-reflection. Ask yourself: What are your goals? What’s your vision for your future as a self-employed professional? Consider not just the financial aspects but also your personal and professional aspirations. For me, goal setting was not a “one-and-done” activity. I revisited my goals and aspirations multiple times over many months (years, actually). This helped me sort through what was on my mind due to current circumstances versus what was on my heart as my life’s passions. Once you gain clarity, clearly defining your goals will help you stay on track, especially when you inevitably lose your way for a period of time.

2. Financial Preparedness

Financial stability is key when making the switch to self-employment. Assess your current financial situation and create a detailed budget that takes into account your monthly expenses, potential business costs, and a safety net for unexpected circumstances. Ideally, you should have at least three to six months’ worth of living expenses saved up before making the leap. Now, I recognize this may not actually be possible. If you can’t wait to take the leap, consider augmenting your self-employment with a part-time gig or side hustle while you ramp up your income level. The first few years can be challenging to gain traction and consistency when generating revenue. Finding another way to fill the gaps will prevent you from quitting on your dream. (True story: I worked part-time at a popular fitness studio for several months in my second year of business!)

3. Business Plan (maybe…)

Conventional wisdom tells you that every successful venture starts with a well-thought-out plan. Your business plan should outline your niche, target audience, services/products, marketing strategies, and financial projections. It’s your roadmap to success and a crucial document for securing any necessary funding. While this is all true, do not let the lack of clarity around a true business plan prevent you from starting your entrepreneurial journey. Your plan can be a simple one-page document or table that captures your initial intentions and forces you to think through the key elements. Don’t over-complicate it or let the process of creating a business plan intimidate you or slow you down.

4. Networking and Building a Brand

Your professional network is invaluable, both in the corporate world and as a self-employed individual. If you are like how I was before making the leap, your brand is centered around the people you work with in person over the life of your career. When pursuing self-employment as a business owner yourself, start building your personal brand and online presence through social media, a professional website, and networking events. Consider attending workshops or hiring a coach to help you refine your personal brand and marketing strategy. You may even want or need to pursue new credentials to aid you in redefining your brand and separating yourself from your former role.

5. Timing Your Exit

When should you give your two-week notice? The answer varies from person to person. Ideally, you want to wait until your new venture is generating enough income to cover your basic expenses and, ideally, more. A good rule of thumb is to have a consistent income stream for at least three to six months before saying goodbye to your corporate job. Again, this is not a one-size-fits-all approach. If you have the flexibility to leave without a consistent income stream, then you may give your notice sooner so that you can fully focus on your new venture.

6. Health Insurance and Benefits

Don’t forget about healthcare and other employee benefits you may be leaving behind. Research your options for health insurance and any retirement plans you’ll need to set up as a self-employed individual. I highly recommend consulting with a financial planner and accountant when it comes to retirement planning, in particular. There are options available to you as a business owner that you likely have not heard of if you were part of a corporate benefit plan throughout your career.

7. Legal and Tax Considerations

Consult with a legal and tax professional to understand the legal structure that’s best for your business (e.g., sole proprietorship, LLC, corporation) and ensure you’re compliant with local regulations and tax requirements. I know… this is not necessarily the fun part of starting a business. However, it is super important. I utilized Legal Zoom to help me establish both my coaching and my consulting firms. The process was super easy with their support! Once you get the official paperwork in the mail stating that your business is a reality, take time to celebrate. This is a big deal!

8. Resilience and Adaptability

The journey to self-employment can be challenging, and setbacks are inevitable. Develop resilience and adaptability to weather the storms. Keep learning, adjusting your strategies, and staying committed to your vision.

Believe in yourself, take the leap, and thrive in your self-employed career!

All my best and more,


For more tips, join my community and receive my free guide to starting your own coaching business- The Coaching Kickstart: Unleash Your Business Potential!

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