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How to Travel Stress-Free While Freelancing

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Preface: in this article I share the major changes I made to my client communication and project management that made my epic travels possible. I then dive into the mechanics of actually going away and keeping your freelance business or agency running…

“Oh god, I don’t want cactus needles in my crotch!”

I climbed up the cliff in a terrified sweat. Normally there would be no reason to panic; we had chosen a climb that was relatively easy and the climbing rope would prevent me from dramatically splattering my brains at the bottom of the cliff.

BUT there was a giant cactus growing out of the rock directly below me.

And it was waiting to impale me if I missed clipping the next bolt. In that moment I had only one care in the world: keeping a firm hold on the rock as I reached for safety.

The cactus in question...
What fear looks like. It's pointy.

So I don’t exactly avoid stress while traveling. From traveling around countries where I don’t speak the language, to riding a rickety bike with bad brakes down a rainy mountain path in Jamaica, to wandering through Pripyat in Chernobyl, there have been some tense moments.

But inevitably when I share these adventures, usually over a few beers, I get asked by fellow consultants: “How on earth do you travel without getting stuck working all the time?”

Today I’m going to share exactly how I avoid that particular stress. Beer not included.

But let’s rewind...

A few years ago any type of travel while running my web agency was demoralizingly difficult.

Such as when I spent Christmas Day glued to the computer for hours fixing spreadsheets and export scripts due to a last minute client request.

Or when I drove 6 hours each way with my girlfriend to visit her parents for Easter weekend, only to spend it completely stressed out and ignoring her family so I could deal with an utterly unreasonable client. Not sure why she still married me...

“Taking time off” was a delicate balance between trying to stay in the moment and wondering what work crisis was about to derail everything. There was no such thing as “off the clock”, and with every passing year, it became harder to reconcile my desire to enjoy life with the workaholic business model that I had built.

Turning that around wasn’t easy. But after much experimentation I fixed the key things wrong with my consulting business, learned some crucial tricks to being able to travel and keep the business running, and earned my travel freedom.

Freeing Your Time and Your Mind: Eliminating The Barriers to Taking Time Off as a Consultant

As part of the brutal process of deconstructing my agency, I identified all the barriers that made “not being at work” impossible. Both in the sense of being able to travel, and in being able to enjoy a normal evening without worrying about work.

These barriers centered around two schedule-invading sources of friction: Client Communication and Project Management

Friction Point #1: Client Communication and Expectations

  • Expectation of constant availability: frequent unscheduled client calls
  • Expectation of tight turnaround requirements (“we need this by end of day tomorrow”)
  • Expectation of constant email responses
  • Frequent false “emergencies” (client feels it is urgent)

Friction Point #2: Project Management

  • Never-ending project work
  • Urgent questions from the team
  • Frequent true emergencies (things breaking unexpectedly)
  • Overtime due to late work

These can be cured by one of two major changes:

Major Change #1: Handling Client Communication the Right Way, Without Being Reachable 24/7

A symptom of a bad client relationship is the expectation that you are reachable constantly, on and off work hours. This is not necessarily the client’s fault:

  • You may be imagining this expectation even though it doesn’t exist (this is probably the top cause).
  • You may have set this expectation with your past behavior.
  • You may have never communicated to the client how to best communicate with you or how the project will run.
  • You may have given the client good reason to be concerned, such as late deliverables.
  • You chose a truly mission critical service (time to rethink your business model).
  • And yes, sometimes people are just unreasonable beyond fixing.

Whatever the reason, eliminating this expectation gets you 50% of the way to stress-free travel as a consultant. Luckily it’s very doable:

Give the Impression of Constant Email Availability… Without Checking Email Constantly

You probably know that you shouldn’t be checking email constantly, and that it becomes impossible to get work done when barraged by email. But how do you break email addiction and still deliver stellar client service?

You can give the impression of fast response times just by following four simple "rules of email engagement”:

  • Commit to checking your email only 2 or 3 times a day, such as at 10am, 1pm, and 4pm (credit to Four Hour Work Week for this breakthrough).
  • For shorter vacations or business travel, you can get away with checking email once a day and setting an autoresponder (“due to travel my responses may be delayed from ___ to ___”). I have done this several times, such as a recent 1 week Jamaica vacation where I dealt with business first thing in the morning then drank scotch and Jamaican beer the rest of the day. More on this further down in “What To Tell a Client When You Go Away”.
  • Respond to all client emails each time that you do check email. If an email requires more than a couple minutes of your time, reply that “you are on it” along with when the client can expect completion. Clients can be very reasonable when they know that they aren’t being ignored.
  • Get rid of the email on your smartphone. If you really need to check your inbox, use webmail. I haven’t had email on my phone since 2007 and the world has yet to end.

Answering email on the schedule above works really well to create the illusion of “constant response” because most clients are used to dealing with other office workers. It’s perfectly normal for an office worker to be in meeting for a couple hours, on the phone, etc. It’s also reasonable for them to be unable to get around to your email after 4pm (meeting, had to pick the kids up from school, or just plain didn’t get around to it).

Detach From After Hours Calls and Email With Peace of Mind

Dealing with work when you’re not working is absolutely toxic.

Email after hours simply shouldn’t be handled until the next business day. By definition, an email isn’t an emergency. This can be easily trained into most clients, and the few that insist otherwise are relationships you need to run away from.

Phone is handled in a similar fashion. Thanks to a virtual PBX service (Network Telsys), calls to my extension hit voicemail outside of predefined hours. No getting woken up at 3am.

Of course the reason we are tempted to check email and answer calls is that true emergencies can happen. I solved this with the phone menu for my company’s phone system: after hours calls receive an option for emergencies that will dial my phone (or someone else) 24/7 and display “Emergency” as the caller ID name.

There’s a subtle psychology with this approach that keeps it from being abused: it throws callers out of the regular contact process and requires them to actively consider whether this is really an emergency rather than dialing blindly. The net result is that the emergency line rings a handful of times a year, usually for good reason (or a telemarketer but that’s another story…).

Use Calendly to Schedule Meetings Instead of Taking Ad Hoc Calls

I strongly discourage unscheduled phone calls in favor of email, and will deflect unscheduled phone calls to a request to book time with me instead to give the issue the time it needs.

I use Calendly to allow clients to easily schedule phone time on my calendar. This serves two amazing functions:

1) It’s very easy to enforce when I’m available, batch calls together, and make travel days simply unavailable for meetings.

2) It removes the mountains of back-and-forth email and accidental double-bookings/time-zone errors that occur with manually trying to agree on a time that works.

Consistency is the Key

Remember, every communication that you make with your clients sets the precedent for future expectations. Once you start to answer emails at 10pm, your clients will start to expect it. If you need to catch up on email during odd hours, use a plugin like Yesware to schedule it to be sent during business hours.

Major Change #2: Rethinking Project Management to Avoid a Constant State of Last-minute Work

Fixing your client communications is half the battle. The other half is projects: far too many freelancers and agencies are locked in a state of perpetual crisis.

“Projects are constantly late, there is too much work, the requirements are out of control, and something is constantly broken.” (Not my words by the way… this is a direct quote from an agency owner who wishes to stay anonymous.)

It’s hard to enjoy travel when you’re battling 10 different fires at any given time.

Fixing this completely goes far beyond the scope of this article, but subscribe to the Freelance Transformation newsletter and we’ll tackle that in time.

However, there are two breakthroughs that have allowed me to focus on the cactus that I’m about to fall on, rather than worrying about what could be going wrong in my business.

#1. Better Project Planning
Solo operators: this applies to you too!

I used to wing projects by the seat of my pants. I was already super busy, so how on earth could I find the time to plan anything?

But a lot of fires stem from wretchedly poor project planning and cost time and stress in the long run. This is a skill that takes time to develop and the only way to build it is practice.

My simple project planning rule: With any project at any time it should be crystal clear, to you, your team, and your client:

  • What major phases are left between now and completion
  • What is currently being worked on, by whom
  • Any client deliverables holding things up

This information makes it easy to spot and deal with problems and delays well ahead of time, instead of facing last-minute crisis situations and crunch time. Yes planning is real work, but the payoff is sleeping well knowing that everything is taken care of and on track.

Notice that I included the client in the list of people who need to be clear about project status. You can avoid a lot of “check-in” emails and unexpected phone calls just by proactively keeping your clients abreast of where things are now and clarifying the next step.

#2. Take a Proactive Approach to Quality Control

The more times you have to go back and forth with revisions for a client, the more your travels will be interrupted by “unexpected changes” you suddenly have to make.

A major cause of this is sending “rough draft” quality work to the client. I get it, testing and review is only slightly less painful than cutting off your toes. But over the years I’ve come to greatly respect the importance of quality control and the major lifestyle improvements that this creates.

Before sending out your work, make sure that it’s correct (or if you have a team, have someone else do it). Make sure software functionality actually works. Make sure that your design fits the agreed upon guidelines and business goals. Make sure that your spelling and grammar are polished at every stage.

It’s not the client’s fault if your work is riddled with spelling errors or that new import script you wrote crashes terribly if there’s an apostrophe in the data. It’s your fault for not doing proper review, and yes you’ll be stuck fixing it instead of relaxing on the beach with a mojito.

Logistics: What to Tell Your Clients When You Go Away

During honeymoon. Clients had no idea I was ice climbing up a mountain. Nor was there any need for them to.

I like to eat my cake and have it too. So my favourite approach is to dangle off cliffs and enjoy Jamaican beer without giving my clients a lower level of service.

This means that most of the time when I am on vacation and/or traveling, my first choice is to say nothing, and simply make sure they are taken care of.

This may seem impossible to do without spending all your time on your computer, but by timing your travel and making the changes that I described above, it’s very realistic to scale back to 1-2 hours of work for shorter trips.

But what if you really truly want to just unplug?

In 2012 I took an epic 2 month trip with my wife through Poland and Ukraine. This was the first true vacation I had in almost a decade and it was legitimately work-free and life-changing. I put my younger brother in full charge of the business, I checked e-mail once every two weeks (to pay payroll) and got a SIM card that only 3 people knew the phone number for. In short, I was free.

I highly recommend that you try this “fully unplugged” approach at least once, particularly if you feel overworked and can’t remember what time-off even feels like. You have two great options to make this a reality:

Option 1: Put Someone Else in Charge

When I decided to take two months off for my Poland and Ukraine trip, I had several people working for me, many clients to keep happy, and a very complex project that was launching several weeks after my return.

Documentation was the key to being able to leave all of this complexity in the hands of my brother. For several months I undertook the painstaking effort of really truly documenting everything about the business: our processes, what to do when things go wrong, the state of all projects, and of course, all passwords and access information. This process was grueling, but it did pay off. In addition to buying my freedom, this type of intense documentation forced me to review and refine every part of how I run my agency.

Of course you don’t have to be operating at my scale or hiring someone full-time to pull this off. A friend of mine is a sole proprietor, and when he goes away a friend who has a very similar business takes over for him for that week and simply sets an email autoresponder with this information. My friend returns the favour when his friend needs to go away, creating a very simple buddy system that works great for short-term trips.

Option 2: The Responsible Vacation Notice

I know many freelancers, including those that work for me, who simply give their clients notice that they will be away and provide ample time to prepare. This is perfectly fine and expected if you have branded your business as being “you”.

A good notice should be personal, sent sufficiently in advance, and clarify exactly how this will impact each client’s work.

A simple but effective template to use when contacting each client:

(Sent 4-6 weeks ahead of your holidays)
Subject: Important Vacation Notice (Feb 1-15th)

Dear Stacy,

I hope the latest changes on XYZ project are treating you well.

I just wanted to give you a heads up that in four weeks I will be heading off on holiday from February 1-15th.

I will make sure that project ABC is done well ahead of time so that you have time to review it and request any changes.

I also wanted to know if there was any other work that you were needing to get done before I return on February 15th? If so please let me know by January 15th so that I can make sure it is taken care of for you before I leave.

I appreciate your understanding and happy to help in any way I can before then.

PS. I will send a reminder email a week before I leave with an emergency contact in case something urgent comes up.

The PS is optional and depends on the nature of your work (software developers: I’m looking at you). It could be the contact information for a colleague who can take over, or an emergency contact such as a friend or virtual assistant who in turn knows how to reach you (I don’t recommend providing your direct information).

If you give clients the right notice and make sure that they are taken care of, you won’t receive any pushback. If someone does raise hell over it, it’s time to end that relationship.

But whatever you do, DO NOT leave your clients high and dry.

The advice above doesn’t give you carte blanche to do whatever you want. For some reason there are freelancers out there who have no problem committing the following relationship-destroying mistakes. I know these folks exist because I’ve fired some of them:

  • Not giving sufficient notice: to build amazing client relationships, clients need to know that they can depend on you. If you can’t offer your services for a period of time, make sure that your clients know well ahead of time and can plan accordingly!
  • Disappearing during a big project, software launch, etc: if you are in the end stages of a complex project, this is not the right time to go away. Your clients need to feel that you are there for them in their big moment, and your disappearance could legitimately be disastrous (no matter how well you plan, last minute changes and glitches always happen).

Getting Going: Small Hacks For Getting the Most Out of Your Trip

Time Your Travels with Your Business Cycle

I don’t believe in making life harder than it needs to be. Yes with the proper planning, virtually any trip you imagine is possible. But it’s far easier to leave work behind when it’s slow, such as June-August and after December 10th (when the business world starts shutting down).

If You Have a Team… Communicate Your Plans to Them

If your travel plans will change your communication with your team at all, make sure that they know what response times they should expect from you. It’s not just clients that you have to take care of, randomly disappearing on your people with no explanation is not cool either.

Take Advantage of Modern Phone Technologies

Managing the phone can be a pain when traveling, but luckily phone technology has come a long way.

There are numerous ways to make and receive calls outside of a traditional phone. Some carriers now let you answer your cell phone calls directly on your computer via VOIP. Using a Virtual PBX service for your business number, you can forward calls to your “extension” to any phone number you please. Long distance calls can be made for cheap using the surprisingly reliable Skype service (the bad old days of terrible calls are mostly gone).

Perhaps best of all, more and more clients are getting comfortable with tools such as GoToMeeting and Skype, bypassing the need for a phone conversation altogether.

Make Timezones Work in Your Favour

When my wife and I spent a month rock climbing in Croatia, I didn’t want to disappear from work for a month (too much planning). Instead we took advantage of timezones to enjoy Croatia during the day, and get to work around 4pm (10am for most of my clients). This allowed me to still work 4-5 hours a day with most clients none the wiser about my travel.

Get Your Mental Game in Order (takes practice)

It’s helpful to remember that most of us don’t do work that is a matter of life and death. No one will die if a marketing campaign comes out late, or if some corporate data entry system goes down.

It’s not that we shouldn’t care (I care deeply about the success of all my clients), but is it really appropriate to have panic attacks over making sure that people will hear about the latest soft drink flavor?

Problems happen. Most mistakes are reversible, and if you focus on building an honest trust-based relationship with your clients, most will be surprisingly understanding if you do mess up. And if they insist on reacting out of proportion, it’s time to re-evaluate working together.

A Word of Caution on Client Service… or How to Royally Screw This Up

It’s easy to mistake the premise of the article as “stop worrying about clients”

The entire basis of your client relationship is based around your clients’ ability to depend on and trust you. It’s how I’ve turned $10,000 website projects into six figure relationships, and it’s probably the #1 way that freelancers sabotage themselves… by being unreliable.

Let me be perfectly clear on what this article is not: the advice above is not an excuse to deliver terrible service or to be anything other than the best damn consultant your client has ever worked with.

The strategies here are based in building clear expectations around how you work together at the beginning, and then consistently delivering on those expectations. If implemented correctly, they should increase client satisfaction thanks to providing a more dependable service level.

How do I take afternoons off for no reason yet get constant compliments on my high commitment to service? I’m consistent in how I communicate and deliver, and clients have come to trust that.

Getting Started on a New Life of Epic Adventure (or even an afternoon in a hammock)

This escape artist lifestyle took me years of experimenting and evolving my business to figure out. Understandably you might not be ready to implement all of this advice today, in fact I don’t recommend it because you will be overwhelmed!

The good news is that you should start seeing lifestyle results with each business improvement that I outlined above.

Consider how nice it would be to not have your phone ringing off the hook all day. Or being stuck in your inbox. How much more could you get done?

Pick one step right now (the easiest for you to implement) and commit to testing it over the next 30 days. Let me know in the comments what you are going to do (and feel free to share any cool travel stories too!)

PS. I did avoid impaling myself on the cactus. Although I still managed to brush my hand against another one…

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