How to keep your girlfriend happy when you’re an entrepreneur

Girlfriends are hard to keep happy no matter what. As a young entrepreneur with very little income, it’s even harder to keep the boss happy.
Kim and I got into one of our worsts fights last week. I don’t even know what started it; all I know is that it was the first time I felt her disdain, frustration, and anger with my career choice. She has been the most understanding, wonderful person this past year and a half, but everyone reaches a breaking point.
At the climax of the fight, I realized what a terrible boyfriend I had been. I made a promise to her and myself that I would not only make more time for her, but that I would use my time efficiently to make her happy.
You see, I have to approach this how I approach my company. In my company, I can’t spend all my time doing C level work or just working for the sake of work; I have to efficiently use my time in the most productive way possible. My job is to keep the company moving forward, not just surviving in one place. Likewise, my job is to keep our relationship moving forward, and not just surviving in one place.
Here is how you can keep your girlfriend happy as an entrepreneur:
1. Wake up early
Such a simple piece of advice, but just so hard to execute. Sleeping in late is the vice of the entrepreneur; we love to wake up late and stay up all night (usually past 3am) working on our projects.
A few things you can do to get your ass out of bed: set three alarms so that if the first one doesn’t work, the next two will; place the alarm away from your bed so that you have to stand up to turn it off; schedule early morning phone call meetings so that you’re forced to wake up early.
It’s a known fact that girlfriends love to go out at night. Wake up early, work your ass off until the evening, and spend the night making her happy. Trust me, this small piece of advice is going to do wonders for your relationship.
2. Don’t fall victim to cuddling
Man this is difficult! If cuddling was an Olympic sport, my girlfriend would win the gold medal.
Cuddling is like C-level work: It’s the useless, pointless emails that you send; it’s the 2-hour long team meetings that are completely unnecessary. You know why cuddling is a trap? It’s because girls love to do it, but it doesn’t count as “doing fun stuff together” or “spending quality time together.”
Girlfriends want to be taken out; they want to engage in active activities with you. Therefore, cut the unnecessary afternoon cuddling sessions and spend them either “spending quality time together” or working hard so that you can take her out in the evening.
3. Plan activities that don’t cost a lot of money and that don’t take up the whole day
Not everything costs money fellas. Take your girlfriend out to a picnic, to a matinee movie, to the museum, or teach her how to play the guitar, skate, or surf. All of these don’t cost a cent or cost very little.
Make her feel special and plan out these fun days that don’t cost a lot of money. It takes up less time than cuddling, and it will count towards “spending quality time together.”
4. Plan out a relationship schedule much like how you plan out your business schedule
Yes, I know this sounds kind of weird, but it really does help. My girlfriend and I now schedule a week of fun!
For example, check out this coming week:
- Monday: I’m taking her skating at Mile Square Park
- Tuesday: Movie Matinee (we’re watching Slumdog Millionaire)
- Friday: Disneyland fireworks
- Saturday: Picnic at the park
You know how much the above is going to cost me? $30 - the cost of two matinee movie tickets, cheese, crackers, and wine. By planning out the week, you do a couple of things:
- You optimized your time so that every moment that you’re spending with her is not idle time; rather, it’s fun quality time
- She can’t rationally complain that you guys don’t do anything fun together anymore because the proof will be in your calendar!
5. Don’t take out your stress on her
I’ve been guilty of this. Entrepreneurship can be stressful, and people take their stress out on the people that they love the most. What’s the best way to maintain your level of stress? For me, it’s following steps 1-4 above.
Waking up early and cutting out cuddling time optimizes my time to do work and keep pushing my company forward. Planning activities that don’t cost a lot of money and planning everything out a week in advance keeps my time as productive as possible and it means the time I spend with my girlfriend is always “quality fun time.”
By following steps 1-4, I have been able to achieve 5, which leads to a happy, healthy relationship.
I hope this helps and please share your tips in the comments section!


Awesome stuff — great advice + raw honesty.
@scott - Thanks Scott. It’s tough, but I’m doing the two most passionate things in my life
Are you in a similar position?
Wow this is one of the best posts I’ve ever read!
Yu-kai Chou’s last blog post..A more elaborated record of the Mixergy Interview with Jun Loayza
@Yu-kai Chou - Thanks yu-kai! That means a lot to me. Thank you for introducing me to the blogging lifestyle
Content rich in every sense. Any can always rely on the comments that are present on the blog, they’re anytime on cue. I love how the articles are provided into readable chunks and not just plenty of slangs. Placement of the content is what I love mostly. The great detail about this site is the fluency and refinement of prose in articles. The all-around look of the blog is great and original. There’s a precise feel about the blog that i love largely. This site is fantastic every time giving neutral analyzes and news. Fairly unique and eye-opening are the ideas stated.
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Haha, excellent. I just had the biggest fight I’ve ever had with my gf of two years also, and it was over me spending too much time with my company and not enough with her. Nice pointers.
Cheers
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@Brian Linton - Hope the tips help! They’ve been proven to work cuz my girlfriend and I are doing amazing!
Keep working hard
Jun Loayza’s last blog post..FDTV Episode 24 - Promote your talents on youtube with Olivia Thai
Bravo Jun - you’re completely right but it works for girl entrepreneurs too
@Caitlin - Definitely! I think it might be even harder for girl entrepreneurs because girls aren’t expected to work so much. I would think boyfriends are less understanding because they’re the ones who are supposed to work all the hours and bring in the money.
How is your relationship doing?
Jun Loayza’s last blog post..FDTV Episode 24 - Promote your talents on youtube with Olivia Thai
If Ryan cut out my cuddling time, I would be pissed. Otherwise, great advice
We do much of the same to manage expectations.
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Sorry I’m not up to date, but does this Ryan of yours work at Brazen? I need to catch up on all of the Brazen gossip I guess…
Ah yes, girls love cuddling time! Remember that episode of friends where Ross does the tuck and roll move. Or was it Chandler? I just remember that it’s hilarious and that I utilize it to maximum efficiency
This is a really great article. I think it applies very well even to those who are not entrepreneurs - but for any young couple who are busy and strapped for cash. I especially like the parts about not cuddling because even though it’s so much fun, I agree that it can suck up so much time without the two people really getting to spend some valuable time together.
I love the cuddling tip the most, so insightful.
I’m surprised how ingrained that is. Girls don’t think cuddling is really spending time together. (adding “valuable” before “time” doesn’t change much).
@akhila - I’ll be honest, I love cuddling as well. Getting out of bed in the morning is so difficult! I am now working super hard to resist spooning for the better of my relationship and company
@Yukai - yea, that one small tip can do wonders for the company and relationship. Are you able to resist?
I love this post, but while the cuddling point is incredibly insightful… i could never get away with it. I’m already walking a thin line and physical contact is one of those things that keeps a couple close.
There are many other ways of physical contact without cuddling. For one thing - Sex!
You can argue that cuddling gets her in the mood, but I believe that cuddling -> sex is one of the laziest forms of getting her in the mood.
Do this: give her a full body massage, have passionate sex, let her go to sleep, and get to work.
Let me know how it goes
Wow Jun, I think I really needed this. Maybe your next venture should be a young entrepreneur’s love&relationship blog haha
@Jarell Perry - That’s not a bad idea at all! I’m actually going to start sectioning my blog up into better, more core categories. Current potential categories: Startup Tips, Lifehacking, Relationships
I also have a few tweaks left on my design so look something much more spectacular in the coming weeks!
Interesting post, Jun!
I’m an entrepreneur myself and am in a [very] serious relationship with my girlfriend. Often times, in those scenarios, it’s easy to take her for granted, or our time.
You’ve got a lot of great stuff here. I’d add, too, that when you plan out the week like you said, especially if you approach it in a manner of “everything is taken care of” that Ive found my girlfriend loves that. I tend to make it more exciting for her too just by telling her I am picking her up, that she needs to bring a casual change of clothes, and otherwise just to enjoy.
I’d disagree on cuddling not being quality time, but only because realistically, you can make anything quality time. It’s simply ensuring a deeper connection feels establish with the other person. The other day, my girlfriend and I had some of the most meaningful quality time ever at a coffee shop, sipping hot chocolate on a cold day. Likewise, a few days before that, we were in fact just cuddling, but the conversation that we were having while doing it was quite meaningful (though there have definitely been times where we’ve wasted a ton of time just cuddling). I would also say I think it’s important that a gf knows you are willing to ‘waste’ time with her in that sense. Maybe not all the time, but on occasion.
The only thing to be careful of when is to make sure that she doesn’t get the impression that she’s just another task on the list.
Good stuff
@Nathan Snell - Nathan, great point. Adding an element of surprise adds flare and excitement in the relationship.
All cuddling time is NOT wasted time, but it’s definitely not A level quality time. The reason I say this is because in her mind, you’re supposed to cuddle. It’s like a no brainer so when you do it, it doesn’t count as anything special in her mind.
In contrast, taking her out to coffee on a cold winter day is perfect quality time. You’re out in the world, seeing new environments, and get to chat over some hot cocoa.
In my case, cuddling usually just turns to sleep, which means a bunch of “wasted” time. The only reason it’s wasted is because I am not developing the relationship or developing my business.
Thanks for the comment Nathan
I kind of do not agree with your blog.
It is very stale and you seem like you are trying to make someone else happy instead of yourself.
I just hope that you actually like doing these things and that she does the planning sometimes too.
sorry to be personal as I dont know u.
Just a different perspective.
but yes girls like myself for instance do like to just hang with their boyfriends and some do count cuddling as spending time together.
some like to sleep in too and stay up past 3am working on projects also
@ScaryMay - Wow, my blog has never been called “stale” before. What do you mean by stale? I feel it is actually very crisp
Making my girlfriend happy makes me happy. I am living a passionate life as I am working extremely hard to build a company that I truly believe in.
I love doing everything that I mentioned. I actually did a follow up video to this post where Kim responds with what she thinks.
It’s nice that you count “cuddling” as spending quality time. Your bf is very lucky
Its gud 2 let ur grl frnd understand ur status espacial finacialy.It hlp 2 calm ur moral & reduce d tenssion in terms of anything related to financy.Put urslf 2geda & everything arround u will b ok.
Hey Jun - I’ve been going through and re-reading your recent posts. I’m three months pregnant and some days for me the hustle just isn’t there. Thanks for the kick in the butt and the motivation to keep working on my passion even through the moments when it is physically difficult.
Anne Good
Anne, I just read through your blog and I’m a huge fan! I had a dog once myself so these blog is really close to my heart.
I’m so happy that my blog has been a source of motivation for you. Please do take it easy though. I don’t want you to strain yourself too much when you’re pregnant.
I just started Awesome Bloggers and I would LOVE to have you as a guest. Lets chat soon about it.
Hope you had a wonderful weekend!
Love the honesty. I think it’s cool to find a “Love & Dating” column in a entrepreneur blog. Shows that you’re not the mr. macho, all business type. Keep it coming!
Great stuff mate!!
I am an entrepreneur myself and I have been in the similar situation. I am going to follow your master tips.
Thanks so much!!
“Raw honesty” for you!
Great post!
If your GF don’t support and understand, it’s time to get a new one. Simple as that.
Very timely post for me bro! Great to be reminded about these things. Cheers!
Man, this couldn’t have come at a better time. Great post and great ideas! Thanks Jun!
Hi Jun,
I’m sorry to hear you and your girlfriend had a big fight. I like your post - a good plan is always helpful. Just make sure you really understand exactly what was bothering your girlfriend. Sometimes it helps to ask the other person to make you a list - so there is no confusion. Also, don’t forget to run your plan by her and see if she agrees cuddling is a huge time waster. ( I have a feeling she may not want to totally eliminate it. Everyone needs downtime and cuddling can enhance it.) Finally, I think number 5 is of utmost importance in every relationship - good call.
Funny post… and honest! Girls also like to be listened to. Sometimes it takes 5 minutes. Sometimes we need a whole hour. We need to know you heard us, weren’t judging us, weren’t trying to fix anything, and that you got everything we said. I’m all cooled down after that.
Such a thoughtful boyfriend. I like it when you say: Keeping your comany moving forward and maintaining a great relationship are the two most passionate things in your life! It should be the same for every entrepreneur!
Why do you refer to your GF as ‘the boss’?
Because she is
My girlfriend who is sitting next to me would you to add “#5: get off Twitter when you are with your girl”
man im proud to have you as a cousin
This is Great advice man! Cuddling is a sure killer! And like you said it does not even count as quality time! Well planning and organization is essential to keep her happy and to keep you from going broke. Great, Great article.=)