How To Balance Ambitious Career Goals With Your Love Life

by / ⠀Career Advice Entrepreneurship Startup Advice / April 7, 2014

Today, I wanted to write about something that I’ve been thinking about for a long time, but haven’t had a chance to discuss with anybody outside of my “inner circle.”

I want to talk to you about how I’ve learned to balance the increasing demands of my career — writing, consulting, building products, flying places, etc — with the real life responsibilities involved in maintaining a happy long-term romantic relationship.

To be clear: I’m not an expert. I’m not going to write about the 5 Love Languages or tell you that everything is always perfect. I don’t claim to have figured everything out. Not by a long shot.

But over the past year, I’ve definitely gotten better.

In fact, my girlfriend Sara would agree:

This is written proof I’ve gotten better. If I ever need it later.

I think the unique challenges that come with having a girlfriend/boyfriend while still trying to hustle hard are worth talking about — and although this is an issue many of my ambitious friends struggle with, I don’t hear people making any good suggestions to improve their results beyond “try harder.”

So I’ll shed a little light on what’s working for me. I hope you find it helpful!

Please leave a comment at the end if you find this info useful — and if you know somebody who could use this type of material, please pass it on.


On Monday, I showed you some of the pictures and video from a mini-vacation that Sara and I took to Vegas last weekend. I got a lot of sweet feedback via email. Thanks guys 🙂

This year (November) will mark our 4 year anniversary and I’m really happy in the relationship right now. We’ve been through a LOT of ups and downs, but for the past year, definitely more “ups.”

Coincidentally, the past year has also been my busiest year ever.

This is a topic for an entirely different post (or maybe even a book!), but what I’ve experienced in career growth, earning power and opportunity over the past 12 months has been nothing short of mind-blowing. Many people would call this type of exponential improvement a “discontinuous leap” — meaning that improvement skyrockets in a wildly unpredictable, positive growth.

4 years ago, I was a server making $2.13/hr + tips— and many of my previous co-workers are still at that restaurant!


I started a series called “The Server Chronicles” to document my struggle at the restaurant

These days, I’m flying all over the world, averaging about 2 trips per month, working on interesting projects and having a lot of fun doing it.

With my friends Rishi and Cesar in Nicaragua on an Under30Experiences trip

In Boston, getting tattoos with my friends Maneesh and Nicole for our new startup, Pavlok. 

I’m having a GREAT time. But damn, sometimes I’m getting 3 hrs of sleep/night. It’s the hustle!


Why am I telling you about me? Isn’t this post supposed to be about relationships?

I’m making these points not to highlight my own achievement, but to pose a question: If I’m doing so much traveling/working/creating these days…how can I afford to spend time building a meaningful relationship with someone else?

Well, let me start by telling you what DOESN’T WORK.

I used to think of time in business vs my relationship in a 1:1 manner.

I’d desperately struggle to spend equal amounts of time with both. 80 hours of work meant 80 hours with Sara.

This was a benchmark that I’d set for myself, and I could never hit it.

I always felt guilty.

On one hand, I knew that the only way I’d be able to grow my business was to work at it tirelessly.

But on the other hand, working at it tirelessly left me with nothing to contribute to the relationship — and as understanding as she is — you can’t check out for 2 weeks to work on a big project and expect there not to be any consequences.

I always felts like I was playing catch up with my relationship — and I never felt like she was truly satisfied with my attention, even when I was there.


Then, I started to play with the “formula”…

One day, it occurred to me…

I’d been so stressed about trying to divide my time 50/50 — but what if I’d gotten the formula all wrong?

What if it wasn’t about quantity, or spending as much time with my girlfriend as I did on my business?

What if it was all about quality?

Over the past 12 months, I haven’t had as much physical time to spend on my relationship as I’d have liked.

But what I have realized is that the ratio doesn’t have to be 1:1 if when you do spend time with someone, you’re completely present.

Think about it. How many times have you been with someone you care about, but at the same time you’re:

  • Scrolling endlessly through your Facebook newsfeed
  • Thinking about what you have to do tomorrow
  • Half listening to them
  • Talking incessantly about your projects, and neglecting to ask them about their day

We’re all guilty of it.

Try this: Next time you’re with your boyfriend/girlfriend, be completely there. Completely.

If you’ve worked for 10 hours, and you only have 3 hours to give them before you pass out, really give them those 3 hours.

And be transparent about it. Say, “Hey, I’m working on a zillion things right now, but I really want to give you my undivided attention now for a few hours.”

Make sure they KNOW that they’re getting all of you (so that you get credit :p)

Then, make a genuine effort to show you’re serious about your time together.

For instance, leave the laptop or cellphone at home when you go out.

I left my computer at home when we went to Vegas. It was terrifying and weird, but I felt free.

And Sara knew I wasn’t there to work. I was there to have fun with her.

It’s not always easy to balance a relationship with a hustle — whether it’s your own business, a demanding job, or school.

But it can be done if you emphasize the quality of your together time, and make it clear on both sides what the focus is.

Am I always perfect with this philosophy?

Hell no.

But this outlook has helped me immensely over the past year. I hope it’s useful to you, too. 🙂



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Parts of this post were originally published by Daniel DiPiazza at

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.