How to Have It All: Living for Now AND Later

There’s a lot of guilt packed into our culture. We hear phrases like “hard work and sacrifice” tossed around to describe virtuous lifestyles.

We’re trained to feel ashamed of having a good time. We can only allowed to enjoy ourselves for an allotted number of vacation days — any further enjoyment is a sure sign that you don’t give a fuck about The Future.

“Hey, would you like to come on this trip to Costa Rica with us?”

“Sorry, I can’t. I have The Future to consider, you know.”

But what good is that sacrifice, really? Does the decision to suffer today for the sake of The Future actually result in a better future? Or are we just depriving ourselves because we’ve been told it’s the right thing to do?

Sacrifices Make Sense — Sometimes

Certainly some sacrifice is a good thing. But how do we tell the difference between a sacrifice that will benefit us and a sacrifice that just makes us miserable for no reason?



When I was building my business, I took a contract that barely covered my living expenses, quit my day job, and bought a pallet of ramen.

I made the decision to sacrifice my short-term comfort for the potential to significantly improve my life in the long run. I felt comfortable making this sacrifice because there was a concrete goal, a timeline, and a measurable outcome.

I wanted to be self-employed (concrete goal). I had three months (timeline) on the contract to either make a livable wage (measurable outcome) — or decide I would be better off hunting for a new employer.

By making this sacrifice, I was able to make the jump from moonlighting as a web designer to working as a full-time freelancer — and this has paid me back many times over since.

Base Decisions on Tangible Criteria

We should all be aware of what our later years will hold. But we shouldn’t be blindly denying ourselves enjoyment today for the sake of The Future.

In order to avoid making unnecessary sacrifices for The Future — and to avoid making decisions that could negatively affect our real future — we need to define what The Future actually looks like.

This could be a standard of living, an exact dollar amount, or whatever you decide your future will require — it just needs to be concrete. Make sure it’s not, “I want to be able to live comfortably.” What does “comfortably” mean?1

If you defined your future as requiring, say, $60,000/year for retirement, and you want to retire at 67, then you’d need to put a plan in place to save at least $1.5M between now and your 67th birthday.2

By creating a plan, you now have a concrete goal with a timeline and a measurable outcome.

Do Whatever Doesn’t Interfere with the Plan

Once you have a real plan, anything that doesn’t affect it is fair game.

Want to go on a trip, see a concert, or blow off work for the afternoon to visit your friends? Do it, as long as it’s not to the detriment of your plans.

When we have a clear plan, the guilt and uncertainty associated with The Future goes away. We can now test the things we want now against the things we want later — and I think we’ll all be shocked by how rarely the two are opposed to each other.

Sorry I couldn’t come with you, but I have my crippling fear of uncertainty to consider, you know.

This is what we’re saying when we turn down the things we want “for The Future”.

Keep the Future in Context

Without context, The Future is just a foggy, looming uncertainty. It has nothing to do with our comfort or wealth in years to come — it’s just a nagging fear that we don’t know what’s next, so maybe we should hedge our bets.

We’d be better off calling it The Crippling Fear of Uncertainty.

“Hey, would you like to come on this trip to Costa Rica with us?”

“Sorry, I can’t. I have my Crippling Fear of Uncertainty to consider, you know.”

Living the lives we want to live today is certainly a threat to The Future. But to a well-considered plan for the future, our happiness is no threat at all.

So we have to ask ourselves: are we holding back because this sacrifice will have a measurable impact on our plans for the future? Or are we just scared of The Future?

  1. For me, that might mean a house made out of hammocks where I’ll be fed various morsels of imported cheese by an extremely well-trained octopus. Your “comfortable” living situation may vary.
  2. This is an incredibly simplified approach to saving money for retirement, and it’s most likely wrong. Please do research and talk to a professional about your own retirement plans.

What to do next.

If you’re like me, the idea of traveling permanently while making a living probably seems like a dream — but you don’t think you can pull it off.

I felt that way right up until I actually boarded a flight to leave the United States back in 2014 — and now I can’t believe I didn’t start living this life sooner.

The secret to a life on your terms — work where and when you want, living anywhere in the world — is remote work. And there’s good news: it’s easier than ever before to join the ranks of location-independent workers around the world.

I want to help you. The best remote workers all have a set of non-technical skills, and I’ve put together a free 6-point checklist to help you master them — and ultimately master your time and ability to work anywhere in the world.

Click here to get the free checklist now.