When to say when | part. 1

If you aren’t willing to walk away, you should never start in the first place.

It’s not giving up if you’re moving on, at least that is what I told myself after informing my partner that I would no longer work for the startup we started two years prior. After two years of full time work while juggling a family of five, it was time to move on. It was in the middle of a weekly meeting when I realized that now was as good as time as any.

Setting a date

It’s not like I didn’t set a date, or even go past it a few times; after two years it was beginning to become obvious that we were not going to get outside funding on the current path we were on. Since we really had no funding other than what my partner had put in to establish the business and build a prototype, I knew it was only time before we would shut down or I would need to move on.

My family was behind me all they way, and we all shared a little bit in the disappointment when I finally made the decision and pulled the anchor. We had sacrificed enough, having burned the boats, so to speak. So pulling the anchor in our case was making do with what we had left in Austin, Texas, a long way from where we started in a Jungle in Central America.

To be honest, I don’t know what I expected my cofounder to say. We had both been with each other  since the idea came to form. From his bodega in Santa Teresa, Costa Rica to a workplace in Austin, Texas; we built a product concept and brand to fit a market we both related to.

Our relationship got weird a few months earlier when we started running out of funds and had to let go of our three paid employees. One stayed on for shares in the company but the other had to work elsewhere to cover expenses.

Our little company was already taking a hit and we still didn’t have a working prototype ready for the market. Not just any market either, we were taking on the chicken and the egg. On boarding businesses with one hand and users with the other. Not an easy task without a product, budget or time on your side.

I set a date in the sand, kind of like a marker to draw you closer to a goal. At first I set a date to launch the app in Austin at a Multi media conference, kind of ambitious thinking for a first time app builder. After two years I set a different date, one that would let me know when to say when. One that reminded me that if you aren’t willing to walk away, you should never start in the first place.

I think that it is important pick a specific date/s in the future and ask yourself a few questions. For me it is 4 months out. Every four months I try to ask myself a few questions to evaluate where I am at with a project, relationship, client, habit etc.

  1. Am you happy?
  2. Do you still have the time?
  3. Is it rewarding?
  4. Is it time to move on?


Are you happy?

Checking in on my happiness, overall well being is the first thing on my list. Different things make us happy at different times. So to ask if I am happy working 50 hours a week without pay is not necessarily the right question. Because what makes me happy about a new project, especially one like this is the potential reward it could offer my family. I would never do something like this myself, I build lifestyle businesses, and never built something to unicorn.

What made me happy was the challenge, and the potential reward. Not the day to day grind or meetings with my partner. That was the price I had to pay. It is when these tasks became something I would dread is when my overall happiness and purpose comes into question.

Do you still have the time?

Even if you are happy, if you don’t have the time or money to keep a new project going you will eventually have to give in. This is different for each person in each situation. Take my cofounder and I for example, we were both entrepreneurs but couldn’t have been more different.

He has a company that he works for fifteen hours a week, a house in Costa Rica with a few employees and and Partner that helps him with his different side projects. He has no kids, no real financial strains. His biggest problem is finding ways to stay busy and new projects to keep him busy.

I on the other hand have a family and a few mouths to feed. Along whit full time hours for the startup I had to work another 15 hours a week on the side just to cover our monthly overhead. I would wake up a couple of hours before the sun to work on my businesses, then work 6-9 hours for the startup, only to spend the last hour or two of the day doing client work.  All of this on top of kids weekend sports, gymnastics, and parties. Needless to say I pretty much gave up on all my hobbies like writing, surfing and gardening to make time for the startup.

Time to me was much more valuable and spread thin over many areas, where my partner had more time than he knew what to do with.


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