How to Shift Yourself Out of Bootstrap Mode

Hiring Help

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Q: What practical steps can I take to help shift myself out of bootstrap mode, where I am doing everything for myself, and into a position to hire some support help?

A: First, congrats on reaching this transitional milestone. You must be doing a lot right to have scaled your business to this point. The good news is the next phase of your business will help you grow even more.

Of course, I get that this is also a frustrating time. To figure out if you’re ready to hire help (part- or full-time), consider these principles:

Working IN your business is not the same as working ON your business. One will grow your business exponentially, both in the income and the freedom you gain, and one will drive you insane. All of us start out working in our businesses. We handle every facet. When we begin working ON our businesses instead, it’s a powerful mindset and time shift.

Any new hire must generate revenue. Now, this doesn’t mean that your virtual assistant is out there selling your online courses for you. Some hires increase your revenue indirectly by freeing you up to pursue clients.

The right person will do the job right. Here’s the thing: If you hire the right person for the job, they will do that job better than you ever have. Wouldn’t that be lovely?

So here are a few steps you can take to apply these principles right now and step out into the next phase of your business growth:

Step 1: Write down what the next five years of your business could look like if you took your hands off the day-to-day, a little at a time, and allowed yourself to show up only as your best self.

Step 2: Put on your research cap and gather some data to see how much revenue even a part-time virtual assistant could bring to your business. Write down every task you do. Rate each 1-5 based on how much you enjoy it and how good you are at it, with 1 being “I hate this and I’m terrible at it,” and 5 being “This is why I was put on the planet.” When you’re done, calculate how many hours each month you spend on tasks rated 1 or 2. Multiply that by your hourly fee. That’s how much you’re already paying someone (yourself) to do those tasks.

Step 3: Finally, look inward at what is truly holding you back. Is it spending the money and returning to a lower overall bottom line? If you’re budgeting, remember that you can start small with a contractor and $100 a month to get used to the mindset shift. If you’re holding back because you don’t trust anyone else to do the work as well as you can, then it’s time to get clear with yourself on what your strengths really are and are not. There is someone out there who can do some of your tasks way better than you. Let them! Your business needs your best.

Related: This Is How You Run a Business in the YouEconomy


This article originally appeared in the Summer 2019 issue of SUCCESS magazine.

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Amy Anderson is the former senior editor of SUCCESS magazine, an Emmy Award-winning writer and founder of Anderson Content Consulting. She helps experts, coaches, consultants and entrepreneurs to discover their truth, write with confidence, and share their stories so they can transform their past into hope for others. Learn more at and on Facebook.

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