How To Balance Ambitious Career Goals With Your Love Life

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:


Screen Shot 2014-03-27 at 12.51.46 AM

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


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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Hey there Raj,

I just realized My first sentence sounds like spam, but it's not! Promise! I was searching on google about this topic and your post popped up on the first page. Thanks for the tips on balancing a relationship with a big, ambitious hustle. The truth is, I am very skeptical about where my relationship is headed. It seems the more focused I am, the more resentful I make my lover... oh well... thanks for the tips though.


@pushfactor you're welcome!

If you don't mind me asking, what did you enter into google that my post popped up?


Hey this is fantastic. I'm in a very good relationship right now too and the balance is something that is often on my mind.

I wrote this in a blog post in December, and it's very much in line with what you've found out:

Don’t believe in “don’t chase the girl, chase the dream”. I wrote about this in my 12 Things post as well. Developing an immunity to rejection and enough dates from ultimately led me to asking out my current girlfriend (and that one technically happened via Twitter, believe it or not). yes, girls can be distractions when pursuing your dreams, but if they are a distraction then that just means it’s not the right girl. The right girl is someone with whom you can share your dream

When you make every second count, you don’t have to count secondsAfter finding the right girl, we began to get to know each other more, getting along great. Even only one month into our relationship, we both felt like we had known each other for much longer. Now at four months deep, we still say we can’t believe it’s only been four months. From time with my girlfriend, I picked up a lesson in quality over quantity. We both have busy schedules and don’t get to see each other every night, and generally have to plan in advance what’s going to happen on a given weekend so we don’t get booked by something else. How is it that we still have this feeling that we’ve known each other for so long then? It’s because we take advantage of the time which we’re given. I learned that when you make every second count, you don’t have to count seconds.

In case you are interested, full post here:

Rich20Something moderator

@RajNATION  Rajiv,

This was an AWESOME post. 

I loved this one:

If you’re not working towards something, what’s the point of working? When you do make that decision to stop making excuses, you cease complacence and enter actively working. There’s a difference, though, between working, and working towards something. Just working is aimless, and ultimately pointless. It means you’re exerting effort to be in the same position as you would be without exerting any effort. Specifically I think this holds true with your job. If there aren’t distinct goals, a clear vision, or whatever you consider to be a checkpoint or end game, then there is no sense of accomplishment--AKA you’re not working towards something; an exercise in futility. Accomplishments breed confidence, which, again, cut fear down by the legs.

So, so good.

Email me - daniel [at], let's chat more!


Hey Dan,

This is really appropriate advice for starting entrepreneurs - it can be a tough thing to balance. Sure, you can tell yourself "It'll just be for a short while, and then later things will settle down and we can spend MORE time together than we have before" - but it's no good to you if that "later" comes and there's noone there for you to spend time with. What is Sara working on? (I won't ask "what does she do" - stupid question!)

My partner (of almost 5 years) is pursuing a corporate career that sometimes means late nights, and days out of town. I could get all  mopey about it, but frankly it's actually quite a good thing, because it gives me uninterrupted time to focus on my projects (which I definitely will email you about soon - so much exciting stuff going on right now!). But when we get busy like that, we schedule time for us - a weekend away for our anniversary, an entire Sunday to make sure we stay connected. 

Relationships + business is a tricky thing - Sounds like you've got it figured out though! :)


Nice.  I've heard Tim Ferriss talk about a similar tip where he's either 100% on or 100% off.  His vacations mean no contact with work.  Good stuff.  

Rich20Something moderator

@TheDarkLlama  I've heard that as well, but I have to say, it's MUCH easier said than done. I did sneak in a *few* emails via cell phone :)


Well said Daniel

Let me know next time your in Boston man!

Rich20Something moderator

@JoshBeetler  I actually am right now! But don't have a ton of time. Where are you at/what are you up to?


@Rich20Something @JoshBeetler  

I'm teaching in Dedham tonight until about 9pm which is a suburb outside of boston.  I'll be up there tomorrow as well.  If you got some time man, I'd love to take you out for some coffee.  you doin some biz in Boston?



@Rich20Something @JoshBeetler @maneesh  

You around tomorrow?  Maybe can I meet you for some coffee. I start at 1:30 so I'd have to leave at like 12:45 to get to Dedham in time if I met you in the Boston area.

my cell is XXXXX if it's easier to communicate that way. Don't break your neck trying to meet up either if your too busy tomorrow for an hour or so


Makes complete sense! Thanks for sharing this remarkable, yet so simple, advice! 

And thanks for giving your fans life-changing, "quality" advice as always!