If you're checking emails, you're not on vacation
- Randy Pausch, Author of The Last Lecture
This quote came from Randy Pauch (RIP), who became famous for his book and Oprah appearance as a dying professer who spent his last year on this planet in a true state of reflection. He gave a separate talk called Time Management, which is one I revisit from time to time as it contains a lot of good tid-bits of information worth retaining. I recommend it to anyone and everyone!
There are many benefits to being a soloprenuer. I've been doing it for the majority of my near 25 year-long career. As a soloprenuer, you can set your own schedule, choose your best clients (and fire your worst clients), and really be regarded as an expert in your field. Of course every scenario in the world has its advantages and drawbacks and one of those major drawbacks of being a soloprenuer is that, a soloprenuer can never really take a full vacation, but there are ways of making it so that if you do go away on holiday, you can make the most of it all while still keeping a finger on the pulse of your business.
Over the many years of being a soloprenuer, I have been able to go away on several vacations and there be no incident whatsoever. Sure, on occasion an emergency or circumstance will happen where I'll have to work to fix something, but if that happens, being prepared is key to being able to resolve the issue as quickly as possible so that I could return to my vacation.
Effective planning is key to a stress-free vacation. Start by identifying your business's slow season and schedule your vacation during this time. Work ahead on projects and meet all deadlines before you leave. For time-sensitive tasks, consider scheduling them to be published or delivered while you're away. If disconnecting for more than a day at a time is not practical or responsible, consider vacation destinations where a stable internet connection is available where you are staying or near-by. Cruise ships are often not a practical choice because Internet packages are often exorbonant. You might have to put on hold any ambition to be too far away until you have partners or employees to cover for you while you are gone.
Set expectations with your clients well in advance. Inform them of your upcoming vacation and provide clear instructions on who to contact in case of urgent matters. This transparency helps maintain trust and ensures your clients aren't caught off guard.
Clearly outline what constitutes an emergency with your clients. Establish a special rate for dealing with these emergencies while on vacation. This approach discourages non-essential interruptions and compensates you fairly if you need to work during your time off.
Even as a non-soloprenuer, when you go on vacation, you usually have someone you trust stop by to feed the pets, water the plants or pickup your mail. Similarly as a soloprenuer, you may have a small network of trusted colleagues, one of whom that you could give termporary access to your network to subcontract for you and field support calls. Give them temporary access to the systems or git repositories that they may need access to while you are gone. That said, while trust is a good thing to have, it's probably good to have at least a mutual non-disclosure agreement or even better a subcontractor agreement in place with any subcontractors that you might have as your backup.
Make your work network accessible via the Internet via a secure VPN connection. My main development machine is a headless virtual machine (VM) on my network that I connect to using Remote Desktop from any other machine on my network. Since I work out of my home, I use an inexpensive Raspberry Pi and WireGuard to give myself secure access to my VPN any time I am away. The PiVPN Project makes setting this up as easy as it can get. It will be important for you to observe your home's IP address. My IP address is dynamic but rarely changes. If you are worried about your IP address changing while you are away, you could consider some sort of dynamic DNS service.
TIP: Don't directly expose RDP to your machines from externally mapped ports. This is one of the single biggest risks in the cyber security space for which you could be denied cyber liability insurance coverage.
When traveling, you need to do a little extra due-diligence to make sure you stay connected and keep yours and your clients' data safe.
Don't keep anything on your laptop that is sensitive or important. If you do, make sure it is encrypted in case your laptop gets stolen or lost while you are traveling. It's also good to make use of built in file system encryption such as BitLocker if you are on Windows or FileVault if you're on macOS. Sometimes you might anticipate periods of disconnectivity and still want to work. In these cases, I would recommend that you only copy what is needed to your laptop (e.g. cloning a git repo) to be able to work on. For added security, I would store these files in a local VeraCrypt valut. VeraCrypt is an open-source, cross-platform application that allows you to mount encrypted volumes that are protected by a password of your choosing. Between that and an encrypted file-system, I would think you could be considered to be pretty safe, but you might consult a security expert to double-check this if the data you carry is extra sensitive. For example, HIPPA regulations may prohibit you from carrying sensitive patient data on a portable device.
Personally, I don't travel with a laptop anymore. I use an older iPad Pro and keyboard to connect to my work network using a mobile hotspot on my phone, a VPN and Remote Desktop to connect as described previously. The fact that the device is older and contains nothing sensitive makes me worry a little less about theft, damage or loss. Cellular data or public WiFi hotspots are increasingly abundant and in-flight WiFi support is more commonly supported than not if you are flying (and RDP has worked fine in-flight for me as well).
If you're traveling internationally, research SIM card options so that your tablet or phone's mobile hotspot can connect to your destination country's cellar data services. I recently traveled to Portugal and I was able to get a data-only SIM card from Vodafone for about 20 Euros (1 Euro at the time was exchanged the the US Dollar at $1.09, so about $22 USD) for the entire 2 weeks I was there. If you bought / financed your cell phone or tablet through a carrier, it's likely that your device is locked and any outside SIM from another carrier will not work. Make sure to call your carrier at least a month before your trip in to ensure your device is unlocked. For some reason, it takes a while for an unlock application to go through. If your device is newer than a year old, it's likely your carrier could deny your request to unlock the device, in which case your carrier probably offers an International plan, currently at approximately $10 per day. If you want to avoid the high cost of an international plan, you can always use an older unlocked phone as your hotspot. If your old mobile device was purchased through a carrier it is likely still locked, but if it is paid off, your carrier has to unlock it (or at least are willing to unlock it, in my experience).
Afterthought: Make sure to pack your chargers and portable battery charger. You'll have to carry anything containing a battery in your personal bag or carry on since it's against FAA regulations to check any luggage containing lithium-ion batteries.
Another Afterthought: If you had to enable an international plan on a locked cell phone, make sure that your celluar provider turns this feature off. My parents accidentally forgot to turn this off after a trip to Europe and got charged unnecessary overages for which they had to call their carrier to get the charges reversed.
BEFORE YOU LEAVE test your mobile setup. Give yourself ample time in case you need to debug any connection issues if it doesn't work on your first attempt. If you're using a laptop or non-cellular table, disable your home's WiFi and connect to your phone's mobile hotspot. If your tablet is cellular enabled, skip this and just disable wifi on your tablet. From there, connect to your VPN using the WireGuard App (available on all major mobile and desktop operating systems) and then use a Remote Desktop App (built into Windows or available for macOS here) to connect to your network's resource(s). If you can successfully connect, you're ready to start packing.
Notice this section is short. Hopefully by this point you'll have done all your preparation and if you're lucky, you won't even need to open a laptop...
Dedicate a short period each morning to check in on your business. This could involve reviewing emails, ensuring automated systems are functioning correctly, or addressing any urgent matters. Limit this time to as little as possible to get off your device and back to your vacation.
To truly disconnect and enjoy your time off, turn off non-essential notifications on your devices. This helps prevent constant interruptions and allows you to focus on relaxation and rejuvenation.
IN CASE OF EMERGENCY - As a soloprenuer, you really need to have a way to connect in the rare occurrence that an emergency is taking place. Have a way for your client or backup contact to reach you. Again, it's very important that you and your clients have a true understanding as to what the definition is of "an emergency" in order to avoid any unnecessary interruptions.
If you must work during your vacation, try to balance it with relaxation. Consider working early in the morning to minimize disruption to your vacation activities.
You've undoubtedly earned it. Cheers!
Show appreciation to the person who helped manage your business while you were away. A sincere thank-you note or small gift can go a long way. Offer to return the favor when it's their turn to go on vacation if you can.
After returning, review and adjust any temporary access you granted to your systems or accounts during your absence.
Take time to review how your business performed in your absence. Identify any areas that need improvement and consider implementing changes to make future vacations even smoother.
Ask yourself: Is what I'm doing a developer task or an administrative task? If the answer is the latter, build a feature so that your customer can do it themselves next time. This approach not only saves you time in the long run but also empowers your clients and makes your product more user-friendly.
Regularly assess and improve your business processes, automation tools, and delegation strategies. The more efficient and self-sustaining your business becomes, the easier it will be to take time off in the future.
Remember that taking time off is crucial for your well-being and the long-term success of your business. As John Branch IV, a successful solopreneur, advises, "We need to prioritize ourselves first before our business, because we are our businesses' greatest asset".
By implementing these strategies, you can create a more vacation-friendly solopreneur business. While you may not be able to completely disconnect, you can certainly enjoy a more relaxing and rejuvenating time off, knowing that your business is running smoothly in your absence.
If you found these tips useful, check out my web application template and developer toolset called LymeStack. I built LymeStack as a single soloprenuer to serve my own needs by allowing me to build the foundation for my client's web applications in a very short amount of time. The toolset also helps me to eliminate hours-upon-hours of repetivive CRUD coding and allows me to get to more interesting tasks that my clients are excited about. The template contains lots of built in self-service administrative functionality and automated error reporting features, making it easier for my clients to fulfill most of their own requests and reduces phone calls and emails, allowing me the bandwidth to actually take a vacation! To find out more about the types of problem our LymeStack Template solves, check out the blog post Getting Started is the Hardest Part. LymeStack is free to evaluate for 30-days. For more information check out our Getting Started guide to get a working app up and running on your local computer in about an hour.
Thanks for reading!