Ask Ash: ‘We Want to Go Abroad for a Year, and Need Advice on How to Sustain Ourselves Financially.'

Dear Ash,

My family and I have been in California since 2012. While I love aspects of it here, my husband and I both have felt like we’ve been stagnating. We came to the realization that we’ve been missing a sense of adventure and spontaneity and curiosity and, well, aliveness.

We chose to move here without knowing a soul, so it started to become clear that we could also choose to leave. I’ve had deep cravings for the seasons—for winter and spring and fall!—and my husband, who is originally from the east coast, would kill for snow. So, we’ve recently resurrected our dream of living abroad with the kids, at least for a year, starting this summer once the kids are out of school.

We want to eat ALL the pasta in Italy, and go hiking in the Alps, and go sailing in Croatia, and maybe spend the winter in Germany. 😍 The goal? Explore the unknown and figure out what’s next.

The only problem is: we aren’t quite sure how to approach this from a career standpoint. We both work in sales for large companies (15 years now at same place) and working remotely is not an option. While we’re both prepared to leave our positions in favor of a once-in-a-lifetime adventure, we would also like to do so responsibly and generate a stable income from the road.

I know you train professionals & families how to set up remote businesses for the express purpose of being able to travel & work from anywhere (I’m looking forward to enrolling in your Selfish School program this year!) so my question is this: is this really something we could realistically do with a sales background? I’m trying to figure out what the shape of this business could look like, who we would sell our services to, and what our options are.

I’d really appreciate any advice you might have to offer to guide our thinking, and get us moving in the right direction!

Your biggest fans,

The California Creeps

Dear California Creeps,

I just hiked up a miniature hill yesterday and practically threw my back out: please take photos of you hiking all over THE ALPS because that is the kind of motivation I need this year (right after I get done feeling like a reaaaaaal lump 🤣).

(In my defense, the hill was steep and the woods were snowy and it was slippery as hell and I was trying real hard to figure out what my property lines are here at the farmhouse. I HAVE AN EXCAVATOR COMING NEXT WEEK SO BRACE YOURSELF FOR THAT NEWSLETTER.)

But, this isn’t about me. This is about you. And you have questions. Good questions! Questions that very normal people ask. Like, am I making a big mistake and can I really do this and what about if I work as a gardener in outer space? Can I still set up a remote business that will let me be in Italy?!?! (Because we all want to be in Italy. Except people who are in Italy. They want to be in France.)

Fortunately, I have ansaaaahhhsss. And the first thing I’m going to tell you is this:

You can absolutely set up a remote business from anywhere if you are in sales. You can also set up a remote business from anywhere if you are in almost any other industry, except for massages and drugs. People getting massages really like you to actually touch them, and people taking drugs really want to touch you. Same, same.

The good news is this: sales is actually one of the best backgrounds to have when your goal is to be abroad. You know why????

Because everybody else sucks at it.

And when people suck at something, that’s an opportunity to make money.

So today, I’m going to run down a list of all the possible options you have for setting up a remote business with your existing skill set. Of course, you could always set up a remote business doing something completely random, like sewing teeny tiny gloves for dolls, but let’s stick to what you know for now. (Plus, teeny tiny gloves for dolls are not as in demand as you would think!)

Then, I’ll give you my best advice on how to get started.

5 Remote Businesses You Could Start Today, So You Can Be Hiking the Swiss Alps By Summer: A Love Story

Ready? Let’s go!

1. The Most Obvious Business: Corporate Consulting
   This is where you take what you do already, and sell your skills independently to companies instead of working for them as an employee. You might be like, that’s crazy, who would hire us to consult on their sales team? And the answer is this: LOTS OF COMPANIES.
   
   You said you both work for large companies, so you’re no stranger to the corporate world—or the way the sales department works. I assume you also have a pretty good idea of how to make a sale, or you wouldn’t have been employed for as long as you have. This means something very important: you have knowledge that other people need.
   
   The people that need this skill? Mid-size companies. You would be surprised how many companies are operating without their pants on. (Actually, you probably wouldn’t be surprised. And actually, the friggin’ phrase is “by the seat of their pants,” but you know what I mean.)
   
   Mid-size companies are an excellent starting point for consulting, because they’re big enough to have a couple of sales people on board, and big enough to accommodate an appropriate budget for your services. In this scenario, you could easily set up shop as corporate consultants that help mid-size businesses optimize their sales processes, work with their sales team, help them score bigger contracts, and add fat dollars to their bottom line. (And no, you don’t need to be there in person to do it!)
   
2. The Cuter Version: Small Company Consulting
   You could also work with small companies who are in a growth stage and are hiring their first sales person(s). They don’t know ANYTHING about how to do this right. All they know is that they need someone to go out and meet with potential clients. And so they’re probably asking their marketing girl, Meghan, who is scared sh*tless of sales, TO DO SALES.
   
   This is a fun opportunity because you really do get to be a hero in this instance, and help a small little company grow. The impact potential is huge. It can be super rewarding. But, just know that they likely won’t have as large a budget. (Though I do remember when I worked for a small company out of college with 5 people, they hired on a sales consultant and the guy was charging $10K/month with a minimum investment of 3 months, so it all depends on which kind of company and what kind of revenue they’re working with.)
   
   Bottom line: you take what you already do, and sell it independently to companies who need it done better than it’s being done now.
   
3. The Popular Version: Online Solopreneur Consulting
   A third opportunity within the consulting sphere is to aim your services at solopreneurs and itty bitty online teams who are running, say, a web design studio and are trying to get bigger design contracts and get to the next level.
   
   The pros of this include the fact that, because they’re already functioning as an online business, you being remote won’t phase them one bit. That’s what they’re used to—they’d prefer you to be!
   
   It’s also another target market that can lead to hyper-rewarding results, since most solopreneurs don’t have a ton of sales skills, and even small increases can mean a huge difference for them. (You don’t need to bring in an extra $20M to be a valuable asset to the company!)
   
   I’d say that the third benefit is that this group is probably the easiest to sell to: they won’t have the red tape that corporate does (existing contracts with other vendors, multiple decision makers, budgets getting exhausted, etc.) Entrepreneurs are fast and nimble and when they know they need help, they’re relieved to be able to find someone awesome and pay for it! They’re also alllll over the internet, making finding clients a matter of figuring out which types of entrepreneurs you want to work with.
   
   The downside, of course, is that most solopreneurs and small online teams are going to be limited in their budget. For that reason, it’s sometimes easier to sell your services as a monthly subscription to this group, rather than talk in terms of $25,000 contracts. ($2K a month for 12 months is a hell of a lot easier from a cash flow standpoint, especially once they start seeing results.)
   
   There is also a fair amount of competition in this space, given that there are many business coaches and you’d have to work to really differentiate yourself as a legitimate power player who means business and gets results.
   
4. The Yummy Scalable Version: Live Online Workshops
   So, you’re awesome at sales. You want to help other people be awesome at sales. You can work with clients 1:1, like we talked about above (it’s one of the fastest and easiest ways to get started!), but you’re also limited in terms of how many clients you can take on. Most people in that position struggle to find enough hours in the day juggling clients and deliverables and admin and taxes and websites and ALL THE THINGS, and you’d be in an even tighter position, given that your goal is to also travel and spend time with your family and enjoy new cross-cultural experiences during this year of experimental adventure. That means that, in a perfect world, you’d only be working during the morning, for example, with the afternoons free, or vice versa. But, that can be also tough to do without severely limiting your income.
   
   Enter: live online workshops. In this version of a remote business, you’re taking your knowledge—how to sell—and packaging it up into online workshops that you can give to clients and students around the world.
   
   The pros to this are HUGE, the first of which is scalability. That means that the business can grow without a direct relationship to your time. For example, when you’re doing 1:1 work, for the business to make money, YOU have to be the product. One hour of my time in exchange for X amount of dollars. Time = money. But, because you are a human with only so many hours in the day, then your business will screech to a halt—and so will your income—anytime you stop working.
   
   On the other hand, when you have a business that scales, you remove yourself from the equation and instead of selling your time, you are selling your knowledge. That’s the product. This means that the business doesn’t have a direct relationship to your time: that product is delivered entirely online, and can be purchased by many people at the same exact time.
   
   For example, if you’re working 1:1 and you charge each client $1,000/month, and you take on 5 clients, that’s $5,000 a month, or $60,000/year.
   
   On the other hand, if you were to give an online workshop and show clients how to do something, instead of doing it for them, then if 300 people registered and each person paid $300 for a workshop, that’s $90,000 in revenue…all from one day.
   
   That’s power.
   
   (You can see examples of this over at Crowdcast, a software for people giving live workshops.)
   
5. The Hot, Hot, Hot, Version: The Online Education Company
   In this version, you’re going bigger, you’re going bolder, you’re going extreme!!! ⚡️ NO GUTS, NO GLORY!
   
   Here, you’re packaging up your knowledge into one big, fat comprehensive online training program.
   
   Typically, a program of this nature runs 6-8 weeks, and can either be done with a series of live classes, or pre-recorded classes that can be accessed on-demand.
   
   While a one-off workshop is appropriate for teaching a smaller, tangible skill—like “how to handle client objections about price”—a comprehensive online training program would be best for learning multiple skills to reach one big goal, for example: Sales School for Hair Stylists, where you’d teach hair stylists how to apply smart sales skills to triple their business.
   
   Typically, these are offered with a combination of pre-recorded video lessons in an online portal, live Zoom calls for Q&A, and an online community where students can connect and submit assignments.
   
   By far, this is the most lucrative of the options, because it not only scales, but offers premium knowledge, packaged into a premium experience, for a premium fee.
   
   That math looks like this:
   
   1:1 = 5 clients at $1,000 each = $5,000/month or $60,000/year
   
   Live Workshop = 300 clients at $300 each = $90,000 / workshop
   
   Education Company = 300 clients at $2,000 each = $600,000 / program
   
   That’s the power of scale + strategy.
   
   This is one of the things I teach inside my upcoming program, Selfish School—which, yes, is opening for enrollment in just a few weeks—because the scalability + power makes it the most flexible and lucrative for the professional or family designing a new lifestyle and making travel an important part of their daily routine. These types of businesses can be run with just four quality hours a day, and allow you to have the rest of your day to actually BE A HUMAN. (Not always the case with some other online business models.)
   
   The downside to this is that it requires a much longer lead time to get established: while you can just start selling your services tomorrow, an online education company requires much more preparation and strategy. You’ll need to figure out the best way to package your knowledge before you can even think about selling it. There’s also a bigger upfront financial investment required to get going: an online education company is going to require a website, a professional designer, a professional photoshoot, possibly a writer or editor to help, course software to deliver your knowledge, possibly extra instructors, possibly an assistant to help with customer service, possibly time in a video studio with video peeps and editors. (This isn’t 100% necessary, but your sales will reflect the kind of investment you make here.)
   
   If you want to see one of these in action, enter your email address here and sign up for the free Dream Business Bootcamp. You’ll see how the whole business works over the next few weeks!
   
   Also, keep your eyes peeled for my very own Selfish School program, also opening for enrollment shortly. 💃
   
   All that said? You don’t have to do it the fancy way: you can run a perfectly healthy online education company delivering your materials via written books + kits…you’ll just have to charge less $$$ per unit, and have to make up for it in volume. That means that you’ll have to do more marketing in order to reach more customers, but it’s also less work to convert per sale with the lower price point. So, if marketing is your jam, then great! But if marketing makes you want to stab your eyes out, then I’d recommend working out a premium option so you can market less, and still contribute meaningfully while earning well.
   

Overall, California Creeps, here’s how I’d execute if I were you right now:

Think about which type of companies + people you might love to work with, and start there. (You’ll be miserable working with clients you can’t stand, so this is important! You could be doing the best work in the world, but if you’re working with clients that aren’t a good fit, your work will be miserable.)

Figure out something they really suck at when it comes to sales.

Create ONE service that focuses exclusively on that.

Brand it with a fun and catchy name.

Become THE people who do THAT, and ONLY THAT. This is how you become memorable and get traction and make a name for yourself.

Reach out to clients and tell ‘em THIS IS WHAT YOU DO.

Start consulting for a fee. Keep it lightweight & simple for now.

See how you like it. See how the offer performs. See how the clients respond. Test the waters. And then adjust accordingly.

BUILD AN EMAIL LIST. This is critical. Don’t wait. Start now. (I’ll talk more about that in the future and inside of Selfish School.)

Once you have 100 people on your email list, advertise a live workshop on a specific topic that totally pains your clients, and charge money for it.

Give the workshop. Then, keep building your email list. Then give another workshop. Then, keep building your email list. Then, keep consulting with clients. Now you’ve got two income streams.

And finally, once you’ve got 1,000 people on your email list, put together a beta program that you’ll give live. Let ‘em know it’s new and they’ll get favorable pricing in exchange for feedback. Run it for 6 weeks. Charge less than your future premium rate, but still more than your workshop. See how it all feels. See how it resonates. Keep testing those waters.

And last but not least? If you’re still digging what you’re doing, then turn your knowledge into a full-on education company that you can run from anywhere in the world while having a maximum impact and maximizing revenue, while minimizing your stress (and having plenty of time to travel, explore, and enjoy your life).

I hope this helps you brainstorm, California Creeps! And to everyone else reading along, I hope this sparks some ideas for you, too.

It doesn’t have to be perfect.

It just has to be done.

And that, my friends, is the key to everything good in this life, I am convinced.