SYS 159: Overcoming Fear of Remote Work: When to Hire Your First Virtual Assistant

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🎙 In this episode, Dr. Steve Day discusses the common question of when to hire your first assistant or virtual assistant. He addresses the fears and reservations that often arise when considering this step, whether you are a solopreneur or an established business with an in-house team.

Steve shares his insights and experiences from helping numerous business owners overcome these barriers and embrace the benefits of working with remote workers. He also offers practical advice on preparing for the arrival of a virtual assistant and delegating tasks to maximise productivity and time freedom.

Overall, this episode provides valuable guidance for those considering hiring their first assistant and highlights the transformative impact it can have on business success.


💡 Hiring a virtual assistant can benefit both solopreneurs and established businesses looking to go remote.

💡 The fears and reservations about hiring a virtual assistant are similar for both groups of people.

💡 Working with remote workers has challenges but also advantages, such as access to a larger job market and more affordable talent.

💡 It is important to overcome the fear of working with someone remotely and focus on building trust and effective communication.

💡 The right time to hire a virtual assistant is when you feel overwhelmed and need more time to focus on higher-value tasks.


00:11 – 💬 “When should you hire your first assistant or virtual assistant?”

12:36 – 💬 “If you don’t have a need to hire somebody, don’t hire them. But if you’ve identified that your existing team is overworked or that you want to put more energy and time into creating systems and documenting your work…then it’s just a case of actually pulling the trigger and doing it.”

17:13 – 💬 “Creating an operation manual for the sake of creating an operation manual is not even a labor of love. It’s insanity. Unless you have an end game for yourself, this is, of creating an operation manual to hand over the work to somebody else, then there is no point in doing it.”

18:32 – 💬 “The sooner you actually pull the trigger and start that hiring process, the sooner you’ll take it seriously and start thinking about what can I really delegate to this person?”

19:14 – 💬 “As soon as you feel you could do with a bit more time each day, that is the moment you should think I need to hire an assistant because I’m currently doing lower value tasks than my worth.”


00:00 Hiring virtual support has challenges but benefits.

03:56 Global interest in working remotely requires adaptability.

08:26 Trust-based approach fosters remote and local success.

10:50 Apps can monitor activity and location. Overcome fears.

15:49 Prepare and communicate to achieve successful delegation.

17:41 Delegate tasks, hire assistants and create more systems.


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Steve used to be a slave to his business, but when he moved to Sweden in 2015, he was forced to change how he worked. He switched to running his businesses remotely. After totally nailing this concept, he spent his time helping other small business owners do the same. Steve’s been investing in property since 2002, has a degree in Computing, and worked as a doctor in the NHS before quitting to focus full-time on sharing his systems and outsourcing Methodology with the world. He now lives in Sweden and runs his UK-based businesses remotely with the help of his team of Filipino and UK-based Virtual Assistants.

Most business owners are overwhelmed because they don’t know how to create systems or get the right help.

Our systems and outsourcing Courses and coaching programme will help you automate your business and work effectively with affordable virtual assistants. That way, you will stop feeling overwhelmed and start making more money.


Steve Day

About the Author

Since 2016, Steve has helped hundreds of business owners to systemise their businesses and outsource their work. In doing so, he has helped them regain control of their lives and create the businesses they set out to build.

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