Entrepreneurs often live in the gray area of homelife/worklife - in fact, that is the reason many of them start their own business! They want freedom and independence from a Monday-Friday 9-5 job. What this means is that their boundaries often don't take the form of traditional workplaces. Right Hands must learn to follow this - if your entrepreneur needs a prescription picked up but is on their way to an early morning meeting, it’s on you. If their car needs gas, you can do it. They’re late to pick up their kiddo from school - step up.
From my experience, this is not something that they make a habit of (generally, they have hired you for more business, less home) but if you can fill in that gap, do it. I promise it will trickle down into other areas of your job, where you reap the benefits of relieving stress in other areas of their life.
Of course, there is always a possibility of them taking advantage of it - this is one of those moments of honesty you need to have with them. Know where your boundary is and stick to it. It will help to mentally walk through various scenarios ahead of time and see what you’re comfortable with. Before you respond, ask yourself a few questions in these situations:
What is my initial reaction to this request?
How would my entrepreneur respond to that reaction?
If I am uncomfortable with the request, what would a professional and helpful response be?
How can I make it clear in the future where my boundary is with this type of ask?
Now, try it out with some real-life situations and see where you fall.
“We’re leaving tomorrow on vacation. Can you take my car, get an oil change, and a new set of tires on it?”
“I totally forgot it’s my anniversary. Can you go grab my husband a present?”
“My kid forgot his lunch at home - would you drop it by the school for me?”
“I need to send out an evite for my high school reunion today - would you mind designing and sending that for me?”
Being mentally prepared for at least a portion of the curveballs you’ll be pitched every day is a way to be a solid and trustworthy Right Hand that your entrepreneur knows they can lean on. And boundaries are ways to keep yourself ready for any business issues that may threaten to derail the day.