How certain do you need to be to jump?

How certain do you need to be to jump?

How certain do you need to be to take a risk? Do you need absolute certainty, say 95% chance that it will succeed? Do you need minimal certainty, say 25% chance that it will succeed? Or, do you need something in the middle?

This is a question that has fascinated me for years and helped me make some big decisions. I think the idea was originally something Andy Stanley said or some other teacher, I can’t recall. But, this premise that absolute certainty is impossible, so we must make decisions based on the risk we are willing to tolerate is interesting.

I find that I need about 50% to 70% certainty depending on what decision I’m making. For big decisions like, “should I take this job?” 70% lets me take the leap. For smaller decisions like, “should we hire someone now?” 50% lets me move forward.

I’m not very risk averse. Sometimes 30% will even do if the failure won’t be too large. Knowing this about myself has let me step out into the unknown many times. It has also allowed me to fail and to bounce back with optimism that the next time will work out better.

How sure do you need to be of something before you step off the cliff? Knowing the answer to that question is surprisingly freeing and helpful when making big decisions. There is no sure thing, it’s just a question of how much risk you are willing to tolerate. I suggest you decide ahead of time.

Innovate or Lose

Innovate or Lose

I’m a bit of a productivity nerd. I think about how to be productive a lot. I have also, from time to time, been a bit obsessive about productivity software. About eight years ago I was using a productivity software called Things. I really liked it. It was well designed and did everything I needed and more, but it had one problem, it would only sync from my laptop to my iPhone over wifi, not through the cloud. I waited for them to innovate and they didn’t do it quick enough for me, so I switched to OmniFocus. OmniFocus has been great, and I have used it for about six years (buying updates and whatnot). But, OmniFocus, like Things, hasn’t innovated fast enough and has been surpassed by Todoist.

Yesterday I tried Todoist for the first time and loved it so much I paid for the premium version the same day. Todoist does everything OmniFocus does (and more) but with a better user experience, making it particularly enjoyable to use.

This experience has me thinking about the importance of innovation. A great product or service is a great thing, but just because it is the best today doesn’t mean it will be the best tomorrow. In a market that is always moving and growing, there are always competitors looking to do it faster and better. OmniFocus, the software that I have loved for years, didn’t innovate and lost my business.

Are you innovating or are you losing?

Moments of delight

Moments of delight

When we were planning the first 48in48, I was convinced that our volunteers needed to have a great experience. After all, the volunteers are giving up an entire weekend to benefit nonprofits, so their experience should be top notch and a little fun. So I came up with the idea of giving them “moments of delight” during the event. That first event we created “moments of delight” by having a give away every three hours, serving surprise deserts (and BBQ) during late hours, and bringing in a famous former Atlanta Falcon to give a pep talk. The volunteer team loved it. Since then, each 48in48 has it’s own “moments of delight, ” and we remain committed to being sure the volunteers love their time with us.

Since starting 48in48, have been thinking more and more about creating moments of delight. How can I create moments of delight for my employees? How can I create moments of design for my kids and my wife?

A moment of delight can be simple, an unexpected moment of fun or a small gift. For my kids, it’s as simple as a tickle fight or bodyslam onto the sofa. For my wife, it might be buying her a new pack of gum, chapstick, or home decor item. For my employees, it might be an afternoon at Top Golf, or a goofy meme shared on slack. I think creating moments of delight can be simple and fun. I think everyone should smile at unexpected moments, and I hope to help provide some smiling opportunities to the people around me.

Longer is easier, and less effective

Longer is easier, and less effective

I was talking with my friend Daniel (from Friendly Human) the other day about brand videos and suggested making a brand video that was four minutes. He responded by telling me that four minutes is too long for a video, although it would be much easier to make. Effective videos are two minutes long. Longer videos are easier to make because you don’t have to cut as much content, but they are far less effective.

I find this idea true in so many other areas of life. When describing a problem, it is easy to go into so much detail that the actual problem gets muddied in the process. Sometimes when people ask a question they tend to dance around it as they think out loud rather than taking the time to ask a well thought out question. These questions are less clear and harder to answer. It’s easy to write a long email that is unstructured, but more effective to write a well thought out short one. It’s easy to set a meeting, not prepare for it, and wing it. But, it is shorter and more effective to set an agenda and prepare ahead of time.

Long communication is easier and therefore the road often taken when we won’t slow down and think. Shorter communication takes preparation, thought, and intentionality. But, the result is well worth it.

Top three benefits of having a virtual office

Top three benefits of having a virtual office

My company doesn’t have an office and never has. At the end of this year, we will complete our seventh year in business with a team of 10 people and still no office. This bewilders some people. Some have argued that we must get an office at a certain point. I would argue that while an office is a great thing to have and has certain benefits, there are benefits to being virtual as well. Here are three of the biggest benefits for our team.

  1. Being virtual is a perk that attracts talented self-starters. The people on our team love the flexibility of a virtual office. They love the work / life balance it offers, the zero minute commute in the morning, and the comfort of being in their own space. These perks attract amazing talent that I’m honestly not sure we could get if we had office space, even the coolest office space. A virtual office also attracts people that are self-starters. These are people that have the discipline to work hard while someone is not watching over their shoulder. Working in a virtual office is a lot like being self-employed, so our team tends to think that way and at that level, which I think gives us an edge.
  2. Having a virtual office gives employees freedom. Our team is free to run an errand if they need to, or pick up their kid from band practice. On our team, it is ok to flex time to balance work life with personal life. But with that flexibility is the rule is that the job must get done on time, no exceptions. A virtual office also gives the freedom to work at whatever location a team member chooses. Some of our team belong to co-working spaces and split their time between it and a home office. Other team members just work from home. Often team members will travel and still work while traveling.
  3. A virtual office creates a fun culture. I know, talking about company culture within the context of a virtual office might seem weird, but having a virtual office means that our team must connect in intentional ways that create a great culture. We regularly laugh (hard) on conference calls, joke on slack and connect on the phone. Our team genuinely likes each other, and that comradery shows through all of our interactions. Then, for the times that we do meet up face to face, it’s like being around old friends. We laugh and enjoy being around each other because that time is a treat that we don’t often get.

There are some drawbacks to having a virtual office too. I will save that for another post.

3 Lessons from WordCamp US Day 1

3 Lessons from WordCamp US Day 1

Some of our Sideways8 team has been hanging out at WordCamp US and so far we are having a lot of fun! Here are a few things I have learned here:

  1. It’s always about people. You might think that WordCamps are about the talks, but they aren’t, they are about the people. I love WordCamps because I meet amazing people and learn a lot from them.
  2. Even good processes fail at first. Sometimes you might start a new process and assume it’s bad when it doesn’t work the first or second time. But even a good process will fail the first few times; it has to be tweaked and adapted multiple times to work.
  3. There is always more to learn. I have been using WordPress since 2004. It is always tempting to think I know it all. Being around these amazing people, I realize I know very little. I’m excited to learn more.

Here’s to Day 2!