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Entrepreneurs on Vacation: Strategies for Making It Happen

The tattoo on my forearm reminds me to “Pause. Be. Connect to joy.” It’s my personal mantra created by me, for me, at a time when I wasn’t doing any of the above.

But it speaks to the value of vacations. Now, I won’t spend pages and words talking about the health and personal benefits of vacations. Let’s all just agree that intentional time off is good for us.

Yet, so many owners and entrepreneurs don’t take time off. They tell me this is because:

  1. They are “too busy.” They are the brains, the braun, the doer, the visioner, the everything. No work means no business.

  2. They “can’t afford it.” A week off means a week of no (or low) revenue.

  3. They have no “backup.” Their business is not organized in a way that transfers responsibility in their absence. Having a senior person to “take over” is expensive.

If vacations are good for us, but we are “too busy, too broke, and too unstructured” to make them happen, what are the solutions? Here's how entrepreneurs can make it happen:

Plan

Get it on the calendar and give yourself time to make it happen. A few months to a year might be needed to prepare your business and your team for you to be away, so start planning early.

Automate

Consider how technology can help you be away. Auto responses, redirect voicemails, or setting up processes and pipelines so your customers are looked after.

Delegate

Asking someone to cover for aspects of your job not only gives you a break, but gives them leadership opportunities to show you other skills and abilities they may have.

Make a Point Person

Someone needs to be between you and the business while you are gone. Who is that, and can they be trained or prepared for this?

Budget

If you know you taking 2 weeks off a year, do your budget under a 50-week cycle. Then all expenses and revenue are represented based on real numbers. Being “off” won’t seem like revenue loss because you have planned for it.

Organize your Cash Flow

If your bank account is feast or famine like your business, that will make vacationing difficult. Pay yourself regularly based on your budget, and don’t let that fluctuate when you are away.

Check in?

If you can’t be “away” completely, decide how to “check-in.” Will you look at emails in the morning before shutting down for the day? Look at your phone at the end of the day before you venture off for dinner? One email can mentally ruin your vacation, but if you have delegated and assigned the right point person, you shouldn’t need to check in often.

Bucket List-it

Make your vacations a true achievement of a goal. You work hard, show yourself your own achievements by going places on your “list” or ticking off the boxes of fun and adventure that hard-work can bring.

Commit

Decide what you and your family need and what and how the business can handle it. Then, commit and be consistent. Don’t overpromise to yourself and then underdeliver. Then even you won’t believe you.

Prioritizing vacations is crucial for maintaining well-being and business success. Implement these strategies to enjoy guilt-free time off and return to work recharged and motivated.