RWDevCon Inspiration Talk – Starting Over by Ellen Shapiro

Ellen discusses what she’s learned from starting over in a new field and why you shouldn’t be afraid to make a change if that’s what’s needed in your life. By Ellen Shapiro.

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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 – Starting Over, by Ellen Shapiro – I hope you enjoy!


We’ve all had times in our lives where we wonder in frustration, “How did I wind up here?”

Maybe you’re:

  • Working a job that drives you bananas.
  • Living in a city or with a person that just isn’t the right fit.
  • Still in the industry that you started out in, but it’s turning into a burnt out husk of its former self.

What I’m talking about isn’t something where you get transferred or your significant other gets transferred or some other force from outside comes along and makes this decision to start over for you.

I’m talking about something where you drive the decision making process. You decide to start over.

Just the mere mention of starting over make some people cringe and I don’t blame them because starting over voluntarily is terrifying.



If you’re starting over professionally, you go over from being someone with lots of experience in your field to someone with zero experience in your field. If you’re starting over personally you can wind up in a city or a state or even a country where you don’t know anyone.

I’m here today to tell you that some of the things that make you fear starting over are myths. If you let yourself be paralyzed by these myths, you can miss out on a fantastic new chapter in your life.

Yes, starting over is scary, but it is not as scary as you think.

A Tale of Three Careers

I want to start by telling you my story because I have gone through three major phases in my life, all of them fairly different from the previous one.

  1. First I was a songwriter.
  2. Then I worked in television production.
  3. Now I’m an iOS engineer.

Every time I made one of these changes I learned a lot of things along the way and I want to share some of my story with you. I call it a tale of three careers.

My First Career: Songwriter

Let us go back in time to a magical place known as the 1990s.

My first career was as a songwriter. I started playing the guitar when I was 10 years old and by the time I was 18 I had a couple of regular gigs here in my hometown of DC. All I wanted was to be the next Sheryl Crow or the next Melissa Etheridge.

I poured so much energy into songwriting. I took all the money that I’d gotten at my bat mitzvah and I combined with a couple of years worth of allowance and I put out an album on my 18th birthday.

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You can still listen to it on Rdio or Spotify. It is called Bridge Over Bottled Water because my humor has not changed. I will warn you that my lyrics contain a heaping helping of teenage angst because I was, well, a teenager, but I’m still very, very proud of that album.

Even after I went to college in Chicago, I spent an enormous amount of my free time playing and writing. I started to pull together a little bit of success. I got my first showcase in a big music conference and I started to book some bigger gigs in Chicago.

As I started to really pour myself into the work that it took to become a successful working musician, I realized, “This is going to make me absolutely hate music.”

It wasn’t the musicians that I played with, they were great, but so many people that I dealt with in the music business were, to put it very mildly, colossal jerks. They treated everyone around like dirt at best.

The toxic attitude that they projected seemed to get exponentially worse as you got even incrementally more successful.

I can't take it anymore!

I can’t take it anymore!

You had to really, really love music to keep loving it after coming into contact with these people. Not loving music anymore was not a possibility that I was willing to accept.

I finally realized making music professionally was not for me and this was a terrifying realization. I had built my entire social identity around being a songwriter and I had poured years of effort and thousands of dollars in trying to make it as a professional.

How was I going to move forward from that?

My Second Career: Television Production

My second career in television production actually started as a result of my interest in music being so strong. My parents, including my mom who’s here today, were generous enough to say, “We will pay for your education, as long as you study something that is not music.”

I had realized that film school could actually be a great way to learn about audio engineering and pick up some practical, creative skills that easily transferred back to music.

Once I decided that a career at music wasn’t going to be for me, I found that I was really enjoying working with audio in a more filmic fashion.

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I was the sound recordist during shooting or post-production sound editor on several films that my friends directed and I had a lot of fun. I learned a lot about how to make things sound really great.

In September of 2003, I moved out to Los Angeles to try and break into the business. When the timing for purely audio based internships didn’t work out, I started applying for internships at pretty much anything that looked remotely interesting.

I got a bite from this brand new talk show that had only been on the air for about six weeks.

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I wound up working at the Ellen DeGeneres Show for almost two years and I absolutely loved it. I worked at House for a couple of years. I also worked on a show called Trust Me for six months.

Then I worked at a whole bunch of failed pilots. Pilots are the first episode of the TV show and here’s how they work:

  • If the network likes the pilot, then they order a full series and it becomes a TV show.
  • If the network doesn’t like the pilot or any of a million other things go wrong, the pilot fails and then it’s essentially locked away in a vault never to be seen again.

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The failed pilots for me were the hardest because as a crew we would all work ourselves into the ground to try and to help make something good and then it was all suddenly gone.

It was like all of that work had disappeared into thin air. No one would ever see what we made. If you’ve ever had a client pull the plug midway into a project, you know exactly how frustrating this is.

I finally got so frustrated with this happening over and over and over again that I realized I had completely lost my passion for what I was doing. If you’re not passionate about what you’re doing, the entertainment industry will completely crush your soul.

I knew I was going to have to start over again but this time it was a lot scarier. I had absolutely no idea what I was going to be able to transfer the very industry specific skills that I had picked up over to something completely different.

I also now had rent to pay and my lovely cat who I had to feed. I had to feed him and me and here he is sitting in a box of his expensive prescription food:

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For a while, I couldn’t even decide what it was that I wanted to do with my life.

I finally noticed during my downtime when my friends were off writing screenplays or shooting YouTube videos, I was trying to figure out how my phone worked. I realized, “Maybe this is what I should actually be doing.”

My Third Career: iOS Engineer

This led to my third career as an actual nerd. I decided to be a professional nerd because I had always been good at tech stuff, at least in comparison to the rest of the entertainment business.

When I first started at Ellen in 2003, I was the only person who knew how to hook up a Mac to a network printer. As I moved from show to show, people started to figure out that I was often a reasonable substitute for calling IT.



I was good enough at IT stuff that I actually put together a decent little side business fixing computers and networking issues for writers and producers and other sorts of people who had a lot more money than time.

I knew I can easily go into IT professionally, but I wanted something more challenging. I realized I didn’t want to be fixing other people’s mistakes. I wanted to be making my own mistakes, damn it.

I was so fascinated by smartphones and their inherent potential that I knew, I just knew I had to learn how they worked.

I found a program through UCLA extension that quickly taught me the basics of object oriented programming and showed me how to make very rudimentary iPhone and Android apps. That confirmed to me, this is what I want to do.

I kept building stuff.

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I made three iOS apps and two Android apps on my own and it was hard, especially back in the dark ages of 2010 an 2011. I found and I inhaled tutorials from this site like air.

I finally got a job and I moved back to Chicago and I kept learning. I kept learning and I kept learning and I worked every spare second I had to keep getting better and I continue to do that every single day.

Four years after I first learned how to program, I am here speaking about how to do it and I am building tools and writing tutorials to make it easier for other people to learn. :]

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Now that you have heard what is essentially my entire life story, I want to take some of the lessons that I learned and make them actionable for you. I want to share the five most important things I learned from starting over, and over.

Lesson 1: What You Are Passionate About Can Change

The first lesson is: The thing that you are passionate about can change and that is okay.

You always hear all sorts of your advice about following passion and this is really, really easy if the thing that you are passionate about is easy to get into and pays a zillion dollars.

It’s a lot harder if the thing that you’re passionate about is difficult or it puts a mental or financial strain on you or your family or if you’re working against any kind of entrenched system that tells you that for whatever reason, what you’re doing is not good enough.

The fact of the matter is the thing that you are passionate about at 10, the thing that you’re passionate about 22, the thing that you’re passionate about at 40 and the thing that you’re passionate about at 65 can all be very, very different.

If you’re doing something because you’re passionate, not just because you want to pick up a paycheck, you have to constantly challenge that passion. Life is short and the time that we have to make an impact can be even shorter if you need good health to do it.

You have to ask yourself the hard question, “Is this still what I want to do with my life?”


Failing to ask that question and ask it regularly can lead to years of dissatisfaction because you are doing what you dreamed of doing, but you don’t realize that the dream belong to a different version of you.

The answer to, “Is this still what I want to be doing with my life,” can remain yes for a really long time. Simply asking that question is a really helpful way to push yourself to work on the things that you’re most passionate about and really get the most out of your life.

But you also have to be okay with the answer to that question being no. You have to be willing to use that response as a jumping off point to figure out, “Well, what do I want to do with my life?”

Lesson 2: Making Lemonade Out Of Lemons

When you get to the point that you realized no, you’re not doing what you want to be doing with your life, you can feel like life handed you a lemon. This is when: Making lemonade out of lemons is a necessity.

In my case, this actually happened both literally and figuratively.

In the literal case, this is a lemon.

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Despite its size being what it is, it is definitely a lemon. It almost hit me in the head when I was walking home from the gym one day.

Any time you have a set back it can be very, very frustrating. It’s like almost getting hit in the head with a giant lemon.

You have to be able to look at a set back and say, “Well, that sucked but it happened and I can’t change that. How can I move forward from here?”

You could spend all your time:

  • Looking at the lemon that almost hit you
  • Lamenting how heavy or how sour it is
  • Thinking about how much better it would be if it was an orange

If you do this, you’re not able to look at the opportunities that the lemon itself provides.

Instead you could say, “Okay, I have this gigantic lemon. What on earth am I going to do with this?”

Sometimes you can actually wind up with a lot of delicious lemonade.

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In the literal case, one giant lemon, it turns out, can make more than half a gallon of lemonade.

In the figurative case, I’d actually originally intended to go back to school and get my master’s in computer science, but I quickly realized when I went to do this that I was not academically qualified. To get academically qualified was going to take years if it could be done at all.

I was crushed for a while after I found this out. Then I realized that moping was going to do me about as much good as staring at a lemon wishing it were lemonade. I had to regroup.

I did some research and I found a more professionally targeted UCLA extension program and I realized I have this lemon of not being able to get a master’s in computer science, but I have this other opportunity that could get me to be a working software engineer much faster. The figurative lemonade has really been my entire iOS career.

Lesson 3: Change Does Not Mean You Failed

The third lesson may not apply to everyone, but for those of us who it does apply to it is a big one: Change is not an admission of failure.

I have always been terrified of failure. I was a go-getter. I was a grade-grubber. I was a goody-two-shoes. Forty other synonyms for complete nerd.



A grade of ‘B’ in school meant that I was slacking. The couple of times I got a ‘C’ it was as if the world had fallen apart, broken until that got pushed back up to at least an ‘A-’.

I’ve always been raised with the idea that if I tried hard enough, I could make anything happen.

Part of why I was so terrified of starting over was the implicit acknowledgement that what I had been trying before just wasn’t working no matter how hard I tried. I thought that it was admitting that I failed.

It took the benefit of hindsight to realize that it wasn’t an admission of failure. It was simply an admission that what I had been trying before wasn’t for me.

When I released myself from the expectation that I had to succeed at every single thing that I tried, starting over with a different thing became far, far easier.

Lesson 4: You Never Know What Transfers

The fourth lesson I learned is: You never know what transfers.

As an example, when I worked in a television industry I’ve worked with a lot of big personalities. People who wanted things the way they wanted them and wanted them that way yesterday. From working with these people I learned the absolutely critical nature of expectation setting.

For the demanding people that I worked for,

  • if you told them something was going to happen to make them happy and then it did not happen, they were furious.
  • If you told them the incremental steps that were going to happen and you did not over commit, they were always happy because they were informed about the progress of what was happening. They could follow that progress.

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I haven’t dealt with anybody in tech nearly as nuts as some of the folks that I worked with in the entertainment industry. Anybody here who’s had to work with a client is probably nodding in recognition right now because that technique that I learned to cope working for total Looney Tunes proved really, really useful in simply dealing with businesses who need to make decisions based on the schedule that you give them.

You will find that when you start over you have skills that transfer over in complete unexpected ways. The things that you learned that you think are very specific to your industry, especially when it comes to dealing with people, can help you out immensely.

Lesson 5: You Can Learn Anything

Finally, this leads into the most important thing that I learned: You can learn anything as long as you know how to learn.

One of the things that always terrified me about starting over was the idea that I would be throwing away everything that I had learned about the thing that I had already been doing.

  • How did knowing how to tune a guitar apply to ordering film?
  • How did knowing how to find a three-foot technocrane the day before our shoot transfer to building a UI pop over controller replacement?

What I realized was that in all of my attempted careers, I’d actually learned how to research things.

Research champion

Research champion!

I learned how to word Google searches very precisely so that it would always give me back exactly what I was looking for. Whether it was:

  • How to play a given song on the guitar
  • How to install a firmware update for a particular Windows machine
  • The exact wording of a very, very long UIGestureRecognizerDelegate method

When I started programming I was already miles ahead of other people in my classes because I could coax useful information out of the Apple and Android docs, Stack Overflow, and other online resources way more efficiently.

The power of learning has become newly clear with Swift.


We have all had to start over again. To come from a very traditionally object oriented language to a more functional one; to learn an entire new syntax, one that sometimes requires us to tie our pinkies to our ring fingers to keep from typing semicolons.

It’s been hard, but if you’ve learned how to learn, and not just how to do one specific thing, you can do this, and we will. I, for one, am so, so excited to be learning this new language.

Starting Over Is Exciting

In conclusion, I really hope that I have inspired you all:

  • To challenge your passion
  • To realize that you know so much more than you think you do
  • To remember you can learn even more than you already know

The next time you wonder, “How the heck did I wind up here,” I hope you can remember not to see change as failure and instead to make lemons into lemonade.

The fact of the matter is that while starting over can be terrifying, it’s also the most exciting thing in the world.

Note from Ray: Did you enjoy this inspiration talk? If so, sign up to our RWDevCon newsletter to be notified when RWDevCon 2016 tickets go on sale!