How to create guilt-free time to spend with your loved ones and still build a successful startup

Photo by MCFull
Ramit Sethi taught me to organize my savings account to save for items/moments in my life that are important to me: House, Gifts, Car, Travel, Wedding, and Just for Fun. Because I am now actively saving money for a goal, I am able to indulge my money on things without feeling guilty about it. For example, this past weekend I took my girlfriend out to an indulging experience at a hotel and spa and used the money in my “Gift” mini account completely guilt free.
I felt like a personal finance PRO. Never before had I dropped so much money and felt guilt free about it!
I learned something else these past few months that is equally valuable for entrepreneurs - I learned how to budget my TIME so that I can spend my time guilt free. An entrepreneur always feels like there is work to do, but if you learn how to budget your time responsibly and accomplish your goals ahead of time, then you can indulge yourself with the time you’ve saved up. Ultimately, this is great for your mind, health, and best of all, for your relationships.
Loving your work does NOT mean you should be a workaholic
For some reason we’ve turned into a culture that feels like the title “workaholic” should be worn like a badge of honor - I’ve seen my peers compare their number of work hours as if they were comparing penis sizes.
The number of hours you work does NOT matter. What matters are the accomplishments that you achieve. This is how I’ve done it and how you can do it too:
Step 1: Establish Monthly and Weekly Milestones
The funny thing about a startup is that entrepreneurs are only satisfied when they’re working and completing tasks. However, don’t forget that aimlessly completing a multitude of tasks is useless if you’re not completing milestones and moving the company forward.
On your laptop, write down your goals for the next three months. Limit yourself to 5 major milestones for each month. These should be large major goals such as:
- Hire a developer
- Get feedback from users and analyze the data
- Implement Crazy Egg and analyze user clicks on your site
- Connect with 2 Venture Capitalists
- Close 5 clients
Furthermore, breakdown each month into 4 weeks. For each week, use a piece of paper to write down exactly 5 major milestones that you would like to hit. Examples can be:
- Write 3 blog posts and drive over 500 views on each one
- Connect with 20 new people on Twitter and establish meaningful relationships with them
- Redesign the logo
- Create a job posting for a developer and interview at least 3 potential candidates
- Apply to speak at 3 conferences about social media marketing
These are actionable milestones that you can concretely hit.
Step 2: Embrace unexpected projects
Do NOT be afraid of tasks that come up unexpectedly. These unexpected tasks are inevitable and must be completed accordingly; however, never let unexpected tasks distract you from the IMPORTANT milestones that you need to hit. Before engaging an unexpected task, ask yourself the following questions:
- What is the priority of this unexpected task?
- When do I have to complete this unexpected task by?
- Will doing this unexpected task keep me from hitting my weekly/monthly milestones?
Once you answer these questions, you’ll be able to make an informed decision about how to proceed with the unexpected task.
Step 3: If you complete all of the tasks on your list, then you can spend the rest of your time guilt-free doing what you please
Breath in the feeling of accomplishment and spend time with your girlfriend (or boyfriend), friends, and family. Since you’ve completed your important milestones, I want you to take the time to make the special ones in your life feel appreciated and valued.
I know you feel that since you’ve finished your milestones, you should get a head start on your other work. Let me put a stop to this right now and say that it is ultimately in your company’s best interest that you relax, take your mind off of work, and spend it with your loved ones. The last thing you want is an angry girlfriend (or boyfriend) who is on your case for not spending enough time with her. This is a HUGE distraction and can lead to missed milestones because you’re trying to save your relationships.
Step 4: If you did not complete all of the goals on your list, then you need to adjust accordingly
If you did not accomplish your milestones, then any combination of 3 possible things could have occurred:
1. You set unrealistic milestones for yourself
If this is the case, then you should re-evaluate your goals and make sure that your milestones next month are adjusted according to your capabilities. The goal is to set an ambitious goal that is possible for you to hit. A missed milestone looks bad on you and is bad for team morale.
2. You were distracted by too many unexpected tasks
Remember, unexpected tasks will always occur. You must be disciplined and realize that many of these unexpected tasks are unimportant and will not push your company forward. If you have trouble keeping this discipline, try this advanced technique that Yu-kai and I have tried:
Write down all of your unexpected tasks in a Notepad on your computer. At the end of your day (perhaps at 12am or 1:00am depending on when you sleep), open up your notepad and complete all of the unexpected tasks before you go to bed. Because you’re sleepy, you’ll rush through these tasks and get them done as quickly as possible. This is a good thing because unexpected tasks are usually low in priority and just require simple grunt work.
3. You need to work harder
When you are working, I want you to hustle your ass off. I’m very serious about my work time and don’t let anything distract me, that’s why I’m able to get so much done in a very little amount of time. There are many things that you can do that will help you work harder and more effectively.
Step 5: At the end of the month, review your accomplishments and reassess your milestones
A startup is very volatile. Goals for next month may quickly change and you’ll need to be able to adapt quickly to stay ahead of your competition. The milestones that you write down on your paper are more like guidelines. If priorities change during the week or month, don’t be afraid to change the milestones on your piece of paper. You know what’s best for your company and you need to make sure that you’re hitting the right milestones that will position your company for success.
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These techniques have greatly helped me lead a more balanced, happier lifestyle. Even more importantly , these techniques have allowed me to keep my girlfriend happy and in love with me.
Now that you know how to make free time available for yourself as an entrepreneur, go out and do it!




Wow, I have Ramit’s book too, and never thought about how those principles can be applied for time. I am not an entrepreneur yet, but I’ve always had that fear of losing my lifestyle if I become one.
I’ll start off creating a weekly to do list and branch out from there. Thanks!!!
Hey Theresa, let me know how your progress goes!
You will have to change your lifestyle as an entrepreneur, but it does not mean that you have to ignore your friends and family.
Good luck!
Great tips here, Jun! This line really made me laugh: “I’ve seen my peers compare their number of work hours as if they were comparing penis sizes.” So true though!
I tend to take on too many projects or outside tasks (to help other people) so I’m going to give your top 5 milestones / month a try… I’ll let you know!
thanks
Glad I could give you a good laugh
Please do keep me in the loop. And if you figure out any new strategies for productivity, please do let me know.
Don’t you think it would take to long to create these lists? Also, doesn’t creating lists make you feel trapped and you’re like in the corporate world?
I started my own company for the freedom. If I’m too structured, I might as well go back to the cubicle…
I don’t think this is true at all Donald. You should take time to create these lists at the beginning of every week or month, but they should take you no longer than 15 minutes to create.
Trust me, this will save you A LOT of time in the long run
Great post Jun, these are definitely steps I’ve had to repeat on more than one occasion. It takes time to get it down but it is oh-so-worth-it once you do. I love the “comparing work hours” line, because I hear it so often! It’s not about how much time you put in, but what you get out of it that matters, and some people just can’t seem to get it. Efficiency is what we’re after here!
Following the steps you listed also dramatically decreases the chance of you feeling/becoming overwhelmed in your work too! Working hard should allow you to play hard too
Yes! Love the attitude Anthony.
Love your work, but make sure to play hard as well.
I expect to see some great things from you
This is well said Jun. Most of the tips here are very common sense if you’re trying to get work done, but they are important to remember nonetheless.
I find that in my role at my job, I am able to identify two or three key milestoneswhich I need to accomplish (these can be very big and a long way off), and then work backwards from those goals to determine timelines and other minor goals that are critical path items. As unexpected work items I can naturally fit them into my workload based on their priority.
Of course all of this can be tested in an extreme ways - I literally had a natural disaster ravage one of my projects last year, and that completely upended all of my milestones and goals. Talk about learning to work on the fly!
Wow, that is pretty intense. You can use that in an interview for the questions, “How well do you work under pressure?”
Glad to hear you’re using these tips at work!
I’m confident that I’ll find the balance between crazy productivity and leisure time eventually (I’m already getting better at it), but this decision has been a constant struggle for me. I can’t seem to not feel guilty when I’m relaxing, but I also know that I need it.
I think passion is a huge factor when it comes to productivity. It’s much easier to set all these milestones and goals when you’re doing something that you deeply care about.
Ah yes, “passion”
It’s so important, but how many people really “love” what they do? I think I will write a post about this: Loving what you do vs Doing what you love
“The number of hours you work does NOT matter. What matters are the accomplishments that you achieve.”
I totally agree. It’s not about quantity; it’s about quality. This should be a mantra for time management methods. It can also apply to study habits.
Great blogpost! Love the way you set your goals and then stick to it without being distract, yet have time to spend with you love ones! Kim is a lucky girl!
I really like the distinction you make between working and performing tasks that add value and move your business forward. As you are well aware successful entrepreneurs must understand this distinction and focus on the latter. In my experience corporate positions focus on time, whereas start-ups seem to be goal oriented. Work smarter, not harder is the required slogan of the entrepreneur.