Indulging Dreams of the Laptop Lifestyle

“What if next year we just quit our jobs and worked from home?” I asked my wife. She stared back, her eyes trying to gauge exactly how serious I was.

My wife and I both work full time.

During the ten months of the school year, my teaching position consumes at least 50 hours a week (that’s eight hours at school plus at least two hours split before and after work each weekday). Throw in a little more time spent in the evenings and weekends, especially during weeks with special events or reporting seasons, and I’m closer to 60 hours/week.

I’m definitely not crying about this situation. I’m fully aware that a ton of professionals and entrepreneurs spend far north of 60 hours per week.

I’m just calling things as they are.

Both my wife and I are very thankful for our current jobs, which allow us incredible opportunities to build relationships, serve others, grow, learn, and utilize our skills. My job in particular allows me the amazing honor and privilege of pouring love, life, and hope into dozens of young adults every day. It facilitates the formation of meaningful friendships with other like-minded professionals with whom I share significant ideals, values, and passions. Every staff team at every school I’ve served with has felt, to some degree, like a family. These are monumental blessings for which I am truly and deeply grateful.

All of that said, I can’t help but notice the ways the world has changed in the last ten years. I can’t help but notice the economic opportunities that technology has produced. I can’t help but notice that online marketplaces reward creativity, passion, and consistency over time. And it’s fun to dream, periodically — however silly our dreams might be — about the possibility of completely flipping the script of our current work lives and working from our laptops.

Rest assured, we’re nowhere near making the leap today, this year, or even next year. We’re well aware that a leap of this magnitude would likely take a year or two (at minimum) to properly set up and plan. Until then, we’re only dreaming.

But How Would You Replace Your Current Incomes?

We’re not exactly sure. Most likely, the laptop lifestyle formula would include some mix of income streams from online sales, marketing services, online courses, book writing, and content creation. How much of the pie each of those slices would make up would likely be determined by the response of the market vs. the passion and time we invest into each. Along the journey, there may be other streams that we discover, too. But those five would likely factor into the mix in some form or fashion for the foreseeable future.

Still just dreaming here … but what follows is a little thinking aloud about the pros and cons of the laptop lifestyle. By now, maybe I’ve lost you — the concept is so ridiculous and laughable that the only reason you’re still reading is to see how deep this madness can possibly go. But maybe you’ve had similar thoughts: like me, you’re not close to making the laptop leap, but a spirit of entrepreneurship tugs at you as well.

If that’s you, consider these pros and cons.

What’s the Draw? Some Pros of the (Successful) Laptop Lifestyle

• Freedom of location. Working from home, Starbucks, oceanside cafes, or even in foreign cities would become everyday options. Our workspaces would be limited only by our access to internet.
• Freedom of activities. This is a joy of entrepreneurship — the right to choose your own work and align your productive activities with your creative talents and passions. Come on — that’s a big deal.
• Freedom of time allocation. The laptop lifestyle wouldn’t necessarily free up more discretionary time — in fact, it might even cost us more hours than we currently work. But it would produce greater freedom and control in terms of how and when our time is allocated.
• A higher income ceiling. Don’t misunderstand me. I harbor no romantic delusions regarding the ease or size of incomes that our new laptop lifestyle would generate in the short term. But the salary grids that my wife and I are currently paid on? Gone.
• Online work is scalable. If you make canoes or quilts, your sales are ultimately limited by your health, energy, and time. But most online work is scalable, meaning it has the potential for limitless growth and reverberating benefits. Digital products, in particular, can generate incomes for years after their creation. That’s an upside worth considering.
• New challenges, new growth. I’m a big believer in the power of the growth mindset. New adversity, obstacles, and opportunities would require skill acquisition and development. It would require some trailblazing. And we’d learn and grow — however uncomfortably — every step of the way.
• Being able to work together. Call us sappy, but even after four years of marriage, my wife and I still love each other’s company. The freedom to work in the same physical spaces would be really, really cool. Sure, entrepreneurship would test us in new ways. But I have no doubt that our relationship would grow stronger than ever.

Cons of the Laptop Lifestyle

• Loss of community. As I said earlier, my wife and I enjoy the relationships formed in both of our current organizations, and those relationships would be sorely missed. By contrast, entrepreneurship can be a lonely and isolating venture.
• Loss of defined mission and purpose. Both of our current organizations also serve people well. Like really, really well. Service is an integral part of their missions, identities, and cultures. It’s worth acknowledging that we’d have to work very intentionally to embrace a similar ethic and avenues of service to others. That would be a spiritual necessity.
• Loss of external accountability. Sure, maybe this one could go in the pros list, stated as ‘not having a boss.’ But there’s something to be said for the work we produce and the hours we keep when we’re working under the accountability and direction of others. With those accountability structures removed, it would be up to us to engage in productive activities in timely and market-appropriate ways.
• Loss of predictable incomes and benefits. Let’s end with the obvious. We both currently enjoy good incomes, generous health benefits, and dependable retirement contributions. Those would all go bye bye with a leap to the laptop lifestyle, obviously, and all the usual costs of living would be immediately thrust upon us. Not only that, we’d be permanently accepting the uncertainty of variable income streams. Not a big deal for couples already in sales, for example, but a very big departure for us.

The laptop lifestyle is an interesting conversation, and if nothing else, this post was worth writing just to arrange my thoughts a little more clearly. For now, our $4,000/month housing costs mean that “little matter” of financial insecurity on our cons list is a big enough deal that we can’t take our dreams too seriously. But the appeal of the laptop lifestyle is there, nonetheless, and it feels good to acknowledge it. It may not be a reality in two years, three years, or ever … but we want to continue to dream and remain open to possibilities.

Have you ever had thoughts about jumping from a guaranteed income into entrepreneurship or the laptop lifestyle? I’d love to hear and learn from your thought process — please share in the comments below.