Before you start: Prepare for the Emotional Realities of Entrepreneurship

As a young entrepreneur, I made mistakes that caused entrepreneurship to be a lot harder than it should have been. These mistakes are not about hiring, marketing, operations, or funding; instead, these mistakes are emotional in nature:

  1. I spent two years hungry, unable to take my girlfriend out to nice dinners or vacation trips
  2. No Roth IRA, no savings, and I didn’t make a dent in my student loans caused a lot of stress
  3. Disassociation with friends and family

A lot of times entrepreneurs think that the hardest part about building a company is building the product and selling it; however, I’ll argue that maintaining a healthy relationship with your girlfriend (or boyfriend), friends and family, and saving money are just as difficult and equally important. Heck, the emotional side of entrepreneurship is probably even MORE important because it’s impossible to focus on work when your girlfriend is upset with you!

How I made it harder on myself

One of the most important decisions in my life was also my biggest mistake – November of 2007, I quit my corporate full-time job to pursue my startup full-time. Sure it’s a proud moment, but at the same time, it was pretty stupid.

The reason I couldn’t save money, pay off student loans, or take care of my girlfriend was simply, and quite obviously, a lack of money. Had I stayed at my corporate job and worked on my startup nights and weekends until my startup generated revenue, then the emotional stress of not having money would have never existed.

Furthermore, I could have used the money I made at my corporate job to hire a team of Virtual Assistants that could do a lot of the startup work for me, giving me more time to work on the important, mission-critical elements of the startup.

How you can avoid my mistake and emotionally prepare yourself for entrepreneurship

It’s pretty simple really – don’t quite your job until your startup is generating sustainable revenue.

Haha, it sounds so easy doesn’t it?

The much harder and more important part is to structure your work and life so that you don’t burn yourself out in the process of working a corporate job full-time and a startup company full-time.

Don’t burn yourself out

Working 8am-6pm on one job and 8pm-12am on another job is extremely tiring and stressful. I know this from first hand experience – it’s a big reason why I quit my corporate job to do my startup full time.

I’ve previously written two blog posts that highlight methods to make the work you do more effective:

  1. How I cut my work hours
  2. Scale your company

I want to highlight 3 key points that will immediately help you become more effective with your work-life, giving you more time to spend with your loved ones:

1. Systems and Operations

A solid system is a document (or video) that allows someone to take over a role without any sort of formal training. For example, you should have a system for engaging a potential client that consists of the following steps in detail:

  1. Sales Associate sends the potential client the Questionnaire that you have developed
  2. Once the Sales Associate gets the Questionnaire back from the potential client, the Sales Associate fills out the appropriate page on your Potential Client PB Works Workspace and emails you a copy of the Questionnaire
  3. The Sales Associate looks on your calendar and schedules a time for a call with the potential client
  4. The Sales Associate creates a conference call at the appropriate time and conferences you into the call
  5. The Sales Associate takes notes during the call in the appropriate PB Works page
  6. At the conclusion of the meeting, your team creates a proposal for the potential client based on the meeting notes

That is just one small part of a full Sales System that needs to be documented completely from beginning to end. With solid systems like this in place, people will know exactly what to do and exactly when to do it, giving you the ability to focus only on the mission critical.

2. The Virtual Assistant

I currently work with Virtual Assistants from Asia. I will of course write a much more in-depth post about how to effectively work with virtual assistants, but this brief intro should be enough to get you started:

  1. Do not hire a Virtual Assistant without solid systems in place. If you don’t have a solid system in place that allows the Virtual Assistant to pick up and run with her role, you will waste a lot of valuable time and money
  2. Morning time (time to start work) in South East Asia is around 4pm PST. Also, take note that Sunday 4pm PST is when South East Asia starts their Monday morning work
  3. You DO have the ability to assign your Asia team to work a Tuesday – Saturday schedule their time. This means they will be working Monday – Friday your time.
  4. Do NOT spend time training a Virtual Assistant that cannot properly do his job. It’s better to immediately fire a VA that is no good than to spend time training him.
  5. My company pays our international team about $3 – $4 per hour

The easiest place to start is Elance. Remember, don’t spend time training an incapable team. Give them the systems that you have developed and have them do the work. If possible, work out a deal with the team you hire that allows you to pay less for a trial run to determine if they are effective at the work that you need done.

3. Accountability

Your team must be held accountable for the work that they do. This is probably one of the MOST important lessons that I have learned, and is something that is essential from the very beginning for a startup to succeed.

For a scrappy entrepreneur, take the following steps to create a solid accountability system that is easy for your entire team to use:

  1. Get the Free version of PB Works
  2. Create an Accountability Folder
  3. Each page should be the name of a person on your team
  4. Organize the page in this way:
    • Week
    • Projects for this week (cross-out tasks as you complete them)
    • Additional Accomplishments

Example of what it should look like:

Week of 1-4-10

Projects for the week:

  1. Write a detailed blog post about emotional stability for entrepreneurs
  2. Create a sales plan
  3. Contact Chris Brogan to schedule a video interview with him

Additional Accomplishments:

  1. Created a mockup design of the Welcome Tab


With emotional stability, you will be well positioned to run a successful and enjoyable startup company. Remember, we are human, and it’s important for us to make time for our loved ones and to make time to relax and enjoy the moment.

Check out all of the posts in the series here: Young Successful Entrepreneur Guide

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Jun Loayza is the Founder of Tour Woo, the easiest way to book a tour in any country. In his entrepreneurial experience, Jun has sold 2 internet companies and lead social media technology campaigns for Sephora, Whole Foods Market, Levi's, LG, and Activision.


  1. James S says

    Nice post on how to manage VA’s … the 4HWW gave a baseline sketch on how to outsource, but this adds needed detail to the equation.

    • Jun Loayza says

      James, I will dedicate a future post just on the topic of VA’s. It’s definitely not as easy as the 4HWW makes it seem like it is.

      But, if you are able to build an efficient machine, the process become very beautiful

  2. says

    I love this Jun…Ur right…taking a systematic approach to your work (as much as possible in a startup) is key to enjoying life with the people that matter most. It’s sooo important to understand your parameters as an entrepreneur. To understand how much time you have, $ and what you believe is worth your investment in both areas. Every decision should be calculated….your guiding parameters will take shape the more experiences you have.

    I always appreciate you perspective and knowledge my friend!

    • Jun Loayza says

      It does sound so calculating doesn’t it? This is the way that I personally have to do it. The only way that I can keep my sanity in check.

      I wonder if there are people who can just do it without planning things step by step and just doing it?

  3. says

    I just want to say that I completely, wholeheartedly agree with not quitting your corporate job until you are making money and have become so busy that you can no longer feasibly perform two jobs successfully. Starting your own business is a great day but one we may jump to quickly at; I know I did.

    But, we learn from our mistakes which make us stronger, right? And, without failing (that’s a strong word) at my first start-up business, I wouldn’t know what I now know.

  4. says

    Thanks for the great post and a much-needed shot in the arm to continue riding the corporate train until I get some entrepreneurial legs. I can’t argue that I’m enjoying the paycheck and benefits. The hardest part is knowing I’m sacrificing my most productive hours of the day working for someone else.

    I’m working on getting my hustle on thanks to inspiring sources like Gary Vaynerchuk, Pam Slim, and of course the great community here at Untemplater. I spent college summers working multiple jobs. It sucked, but it paid off. Need to get back into the fight through the pain mode. Corporate life has a way of making you soft.

    Looking forward to the post on VAs. I’ve been interested in the concept since first reading about it in the original 4HWW but haven’t done much research.

  5. says

    Jun – Thanks for your post man. I’d be fascinated to learn more about Virtual Assistants. Sounds like a really great way to maximize one’s profitability.

    I want to commend you for taking the plunge to do a start up full-time. I was just having dinner with a venture capital friend and his wife last weekend, commenting on why the VC wouldn’t give them seed money, bc the founders WOULDN’T quite their day jobs at Google! Interesting huh? It’s a catch 22, and somehow, part time start uppers need to convcince the ones with money they are dedicated.

    The one thing I have to say about working brutally long hours, is that when you hit age X i.e 30, you’ll look back and feel extremely PROUD of yourself, as well as relieved. The work you put in now is the foundation for your future.

    Thanks again.


    • JunLoayza says

      Thanks for the words of wisdom.

      Yes, I will be very thorough with my VA post. I think it’ll be super beneficial for individuals and companies

      Meet up soon

  6. Mike Key - Entrepreneurial Ninja says

    Great write up man. And good luck on the plunge. I like you quit before I was making any real money. I had however saved up 6 months of living expenses. It was my personal motivation to get the ball rolling before the bill collectors started calling.

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