RWDevCon Inspiration Talk – Opportunity by Jake Gundersen

Check out Jake’s story of how he’s found a happier, more exiting career: by saying ‘yes’ to opportunities that forced him out of his comfort zone. By Jake Gundersen.

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Note from Ray: At our recent RWDevCon tutorial conference, in addition to hands-on tutorials, we also had a number of “inspiration talks” – non-technical talks with the goal of giving you a new idea, some battle-won advice, and leaving you excited and energized.

We recorded these talks so that you can enjoy them, even if you didn’t get to attend the conference. Here’s our next talk Opportunity by Jake Gundersen I hope you enjoy!


Part of this talk is going to involve a little bit of audience participation: I want you to think back in the last three or four months of your career. I want to ask by raise of hands who has ever felt like this:


Like you have no idea what you’re doing?

Or have you felt like this guy:



Like you’re right about to just fall on your face?

Or have you been jealous of somebody else’s career? Have you felt like you would like to be working on those kinds of projects or at their level?

Some of you probably said yes to some of these questions. :]

But I’m Safe Here!

On the other hand, some of you were probably thinking, “No. You know, I’m pretty good with where I am. Things are going smoothly. I’m comfortable. I’m good at what I do. Things are all good.”



I’d like to argue today that if you’re feeling that way, if you feel like all things are all good, you’re probably playing it too safe. You’re probably not taking enough risk or pushing yourself.

There are probably opportunities for you to be doing work harder, more interesting, more difficult than you’re doing now that you just need to reach for it.

This is great quote by John A. Shedd that says:


“A ship in the harbor is safe, but that’s not what ships are for.”

It’s really tempting to play it safe. We get used to being good at what we do. We’re comfortable with our skill sets with the people that we’re working with, with the environment that we’re in.

In sailing there’s tons of risks involved in embarking on a new journey. Your ship could sink. You may not know anything about sailing or you might encounter some unfriendly natives.

I think there are opportunities out there for each of us that we just need to reach for. The only way to get to those opportunities is by stretching ourselves, by taking more risk. I think that we can surprise and amaze ourselves of what we’re capable of doing if we put ourselves out there.



My Experiences

I’m going to talk a little bit about some of my experiences, my story. After school, I started out as a financial analyst at a hospital, a super secured job.

I was looking at spreadsheets all day, everyday. It wasn’t super interesting and I was in a cubicle.

I was able to take advantage of a series of opportunities. Then I was able to become a successful iOS contractor and author.

I’ll tell you a little bit about my transformation. I’m going to tell you three stories.

My First App

The first story is about opportunities that come to you. A little bit about after I graduated from school, a buddy of mine I went to school with came to me and said he wanted somebody to build him an IOS app.

I had been a life long wanna-be programmer. Maybe ten or fifteen times throughout my teenage years and early twenties, I had attempted to learn programming from books just like this one.



I got in two or three hundred pages in and I would just get bogged down; the learning curve was too steep. I get bored and I’d abandoned my attempt to become a programmer.

When my friend asked me how it was going, I said it was something I was super interested in, but it was also something I really wasn’t capable of doing. When he asked me, I was watching the Stanford iTunes course. Some of you guys may have watched it, right?

It was great but I still didn’t know what I was doing.

  • The word delegate was thrown around a lot. I had no idea what that was.
  • I couldn’t figure how to use interface builder.
  • The navigation stack was a great mystery to me.

When he asked me to do it, I almost said no but he said, “Look, Jake. Why don’t you just try it? Give yourself a month. If you can deliver something in a month, we’ll pay you. If not, you know, we’ll go find somebody else. No harm, no foul. ”

That little bit of opportunity was enough that I started having an objective and a deadline and a target, which narrowed the scope of what I was trying to do. Thus, I was able to move through it.

I found an online video that showed me how to put a table view controller navigation stack inside of a tab view controller and that unlocked the whole project and made it possible.

first app

You can see, it’s not an amazing app. It’s very simple but at the time, it was a big deal because it was the first time I’ve ever been able to complete a project and get paid for it and call myself a programmer and it was somewhat legitimate.

This was huge. It changed the way I thought about myself. It had this effect on my psyche. Suddenly, I felt like things that I’d always wanted to do that just felt too hard where now within my reach.

I was so close to saying, “no.” Had I said, “no,” I think the whole course of my life would have been different. I don’t think I’d be programming at all today. I’m very happy that I am.

That opportunity led to others.


I worked with that same friend. We did two or three projects together. Most recently, we went to the White House Game Jam last year. Bigger opportunities grew out of that smaller one.