Podcast: Download (Duration: 38:46 — 44.6MB)
The way to take a vacation without your small business falling apart is to build a 3 to 4 week content buffer in advance, delegate one repeatable process to your team every 6 months, and go in expecting to accept that a handful of small things will drop. On this episode of the My Wife Quit Her Job podcast, my co-host Toni and I compared notes after I got back from a family trip to the Olympics in Paris and Toni finished a five-week house renovation while running her client work.
The context is important. This advice is for founders with a small team or no team at all. If you own a 200-person company with layered management, your vacation strategy looks entirely different, and it took the owners we know a decade of hard years to get there. For the rest of us running lean, the plan below is what actually keeps the business intact.
Below is the exact prep we each use to buy time off: buffer building, delegating one process at a time, flipping your work schedule when life forces it, and the honest conversation about what has to be allowed to slide.
Get My Free Mini Course On How To Start A Successful Ecommerce Store
If you are interested in starting an ecommerce business, I put together a comprehensive package of resources that will help you launch your own online store from complete scratch. Be sure to grab it before you leave!
Table of Contents
Key takeaways
- Build a 3 to 4 week content buffer before any real trip. Add one extra piece of content per week for the month leading up to your vacation instead of trying to batch it all in the final week.
- Delegate one repeatable process every 6 months. Film every last little step on video, hand it off, and stop touching that process forever.
- When chaos forces you off your normal schedule, flip your hours instead of fighting them. Working 3 to 7 pm in daylight beat working 4 to 8 pm in a dark house under construction spotlights.
- Book a hotel or Airbnb for a “productivity retreat” when you need to catch up. Removing every household distraction produced more focused output than a full home office day.
- Accept in advance that one YouTube video, one blog post, or one TikTok will not go out. Nobody’s career ended from missing a single upload.
- Take two kinds of vacation each year. The adventure trip (which is exhausting) and the do-nothing trip (which is actually restful). One does not substitute for the other.
Why do most small business owners struggle to take a real vacation?
Most small business owners struggle to take a real vacation because they cannot mentally switch off, they have not documented their systems well enough to hand them to anyone else, and they treat their entire buffer as a reserve they refuse to use. The result is a “vacation” spent monitoring email and putting out fires from a hotel Wi-Fi connection.
An added wrinkle for lean online businesses: every family cruise Toni and I have taken has been derailed by a website hack, a credit card compromise, a domain expiration, or an employee getting sick at the wrong time. Boat internet in 2014 was molasses, and even today’s improved cruise Wi-Fi forces the choice between paying for a package or actually disconnecting.
The mental disconnect is the bigger problem. Working a day job means the brain switches off at 5 pm. Owning the business means it never does. Any real vacation plan has to account for that.
How much content buffer do you need before a small-business vacation?
For a two-to-three week trip, plan for a 3 to 4 week content buffer built up over the month leading into it, not the week of. The math is simple: one extra piece of content per week for four straight weeks gives you a full month of runway without any single week feeling brutal.
Trying to batch a month of content in the final week before a trip is where most small business owners burn out and cancel. Front-load one extra deliverable per week starting a month out and the vacation prep becomes almost invisible in the calendar.
The buffer is meant to be used. If your buffer is topped off when you leave and half-depleted when you return, it did exactly its job. Feeling stressed watching it drain during the trip is a sign you have not internalized what a buffer is for.
How do you delegate work in a small business before you leave?
The most effective way to delegate work in a small business before a vacation is to pick one repeatable process, film every step of it on video, hand it to one team member, and then stop touching that process forever. Trying to delegate everything at once in the two weeks before a trip is how founders end up doing all the work anyway plus training on top of it.
Toni’s rule is to give any real delegation project a full year to stick. Trust the person on small pieces first, expand the scope quarter by quarter, and by the time you take a big trip, most of the day-to-day is already off your plate.
For a physical process, film literally every step. Before this Olympics trip, our print production kept breaking down on us, so we spent a week filming a crap ton of video covering every last little thing about running the printers. We handed the videos to one employee, walked her through the material a couple of weeks before the trip, and now that process is off my plate for good.
How do you flip your work schedule when life forces you off your normal hours?
To flip your work schedule when life forces you off your normal hours, do the location-dependent work when it has to happen and shift your client or content work into the leftover block, even if that leftover block is 3 to 7 pm. Trying to protect a normal 9-to-5 while everything else is on fire wastes the daylight and produces worse work in both jobs.
Toni’s example: renovating a dark house with no lighting made painting from 4 pm to 8 pm impossible without 100-degree construction spotlights. Flipping to house work from 9 am to 3 pm in natural daylight and client work from 3 pm to 7 pm produced more of both.
The pro of running your own small business is that nobody notices when you rearrange your hours. Clients had no idea Toni was working 3 to 7 pm for three weeks. As long as you are responsive on your phone during normal hours, the schedule flip is invisible.
Why booking a hotel for a “productivity retreat” produces more focused work
Booking a hotel or Airbnb for a two-day productivity retreat produces more focused work than staying home because the room strips out every household interruption. There is no broken appliance to fix, no laundry pile in the corner, no neighbor at the door, and no half-finished project across the hall pulling you into a 10-minute detour that becomes an hour.
Toni pulled this off unintentionally by moving into a hotel and Airbnb during the first three weeks of her house renovation. She got a ton of work done and built up enough buffer to absorb the second half of the renovation with no client-facing disruption.
This is worth doing on purpose when you have a real deadline or a stretch of neglected work. Points hotels are cheap, the room forces monkish focus, and two days often produces what a week at home would.
What has to be allowed to drop when you take a real vacation?
The honest answer is that one or two small deliverables have to be allowed to drop when you take a real vacation, and the founder has to decide in advance which ones. A skipped YouTube upload, one blog post that does not go out, a TikTok that does not get published. None of these end a career.
The counter-example most people know is Simone Biles pulling out mid-competition at the Tokyo Olympics for mental health reasons. She came back to Paris as the most decorated American gymnast of all time. Stepping away at the right moment did not ruin her; it reset her.
The trap for a founder is the identity piece. In the US especially, “what do you do?” is the first question at any social gathering, and small business owners feel like every dropped output is a personal failure. Stepping back for two weeks is not the failure. Refusing to step back until you burn out is.
Two vacation types every small business owner needs
Every small business owner needs two kinds of vacation per year: an adventure trip that is exhausting but memorable, and a do-nothing trip that is actually restful. One does not substitute for the other.
- The adventure trip. Every day scheduled, up at 6:30 am, chasing museums and excursions and the “get your money’s worth” mindset. You come home tired, often sick, and needing a week to catch up. Worth doing, but not restorative.
- The do-nothing trip. Beach, pool, 16 books in a week, no schedule. This is the one that actually resets you. Toni does one of these annually; I mostly do the first kind and pay for it.
If you only do the adventure trip, you will come home more depleted than you left and blame vacations in general for the exhaustion. Book the do-nothing trip separately.
Frequently asked questions
How far in advance should a small business owner start prepping for a vacation?
Start prepping 4 to 6 weeks out for any trip longer than a long weekend. Build the content buffer by adding one extra deliverable per week, hand off any recurring process you can film in a day or two, and lock in a backup for customer service. Two weeks of prep is not enough for a two-week trip.
Can you actually take a vacation as a solo entrepreneur with no employees?
Yes, but only by front-loading content and lowering the bar on real-time responsiveness. Batch 3 to 4 weeks of scheduled posts before you leave, put an autoresponder on email, and accept that anything time-sensitive that hits your inbox mid-trip will wait until you are home. If a solo business genuinely cannot survive 10 days without you, that is a systems problem, not a vacation problem.
What is the biggest mistake small business owners make on vacation?
The biggest mistake small business owners make on vacation is refusing to unplug and then not enjoying either the vacation or the work. Checking Slack from the beach ruins the beach without actually solving the work problem. Either be at work or be on vacation; the hybrid ruins both.
How do you handle a business emergency while you’re traveling?
Decide in advance who is empowered to make what call and how they will reach you. For most small businesses, that is one trusted person with a decision-making tree covering the top three likely fires: payment processor issues, hosting outages, and customer service escalations. Everything else waits.
Should you tell clients you’ll be on vacation?
Only for the clients who have real-time expectations, and only for the exact dates you will be unreachable. Most client relationships in a small service business run just fine on a one-day response time, which almost any vacation location can support. Overcommunicating that you will be gone often creates more anxiety on both sides than it prevents.
How do you get back into the routine after a vacation?
Give yourself one full recovery day at home before your first work day back, and do the highest-friction tasks first. Answering the accumulated email backlog before starting real work is a common trap. Do one substantive piece of real work in the morning, then process email in the afternoon.
I Need Your Help
If you enjoyed listening to this podcast, then please support me with a review on Apple Podcasts. It's easy and takes 1 minute! Just click here to head to Apple Podcasts and leave an honest rating and review of the podcast. Every review helps!
Ready To Get Serious About Starting An Online Business?
If you are really considering starting your own online business, then you have to check out my free mini course on How To Create A Niche Online Store In 5 Easy Steps.
In this 6 day mini course, I reveal the steps that my wife and I took to earn 100 thousand dollars in the span of just a year. Best of all, it's absolutely free!
