181: Finding Your Next Steps to a Career that Fits with Avery Roth



So, you’ve decided on a career overhaul, but aren’t really sure where to go or what to do next?

First, give yourself props for having the self-awareness to come to the decision to make a career change.

Self-awareness is something that we’re not necessarily taught or born with. It’s a kind of thing that you have to develop. The more diverse experiences you have, the more you can tune into that. You build up a habit of noticing and observing yourself as you’re having different experiences. That helps you take data away that allows you to make smarter choices going forward.

Avery Roth

You hear us refer to the “journey of career change” because it is a path of learning not only what type of career you want to pursue, but you learn so much more about yourself – your wants, needs, values, strengths, life goals, by doing the research to find that next step in your career.

Once people decide to change their careers, they often hit roadblocks when it comes to next steps.

Changing careers can be a difficult and overwhelming task, but we’ve outlined the process that will help you figure out how to find a career that fits you and get you from your idea of your next career to actually making it happen.


Once you walk through the framework provided above, you’ll have a solid background on why it is you like and don’t like certain things about a job and you’ll be able to learn more about what job might suit you.

By following the research steps and sifting through your brain dump, you’ll be able to build a profile on the type of role that fits you. When you have that profile, it becomes easier to flesh it out to direct you to your next steps on your career journey.

But, don’t be too hard on yourself if you’re still finding you struggle as you work through the steps listed above.

Career change is difficult stuff. That is why we’ve created the Career Change Bootcamp program that was created to guide you to build a strong foundation that will go even more in depth to help you determine what it is you want out of your next career.

Read more about it here or visit our Career Coaching resource for a more personalized one-on-one career advisor.

Scott Barlow: Welcome back to the Happen to Your Career podcast. I am more than ridiculously excited for our guest today because we have with us our Career and Business Coach, Avery Roth. She’s not so new to the team anymore but it’s the first time she has been on the show and the first time you get to hear her story. I’m excited to share it. Welcome Avery.

Avery Roth: Hi Scott, how are you?

Scott Barlow: I am ridiculously fantastic. We may need a drinking game for the number of times ridiculously gets uttered in this episode. I am ridiculously excited because I’ve been looking forward to this conversation. Obviously you work with us at Happen to Your Career but you also have a few different things going on and have evolved your career over the years. We are going to get into all of that. I am excited to find out more about you and there is probably plenty I do not even know. At the end I want to take the opportunity to answer reader and listener questions. Sound good?

Avery Roth: Sounds ridiculously awesome.

Scott Barlow: You’ve done coaching and consulting. How do you describe what you do now and what you do on Happen to Your Career?

Avery Roth: Primarily I’m a coach. Most recently I’ve coached start-up founders and individuals on how to pivot in their business and lives. I’m an expert in transitions.

Scott Barlow: An expert pivoter.

Avery Roth: Exactly. After doing many internships in different fields in high school and college I ultimately went into finance and finance markets working as an advisor and investor in the equity markets. I did that for about ten years. At that point I burnt out. Ultimately I realized I wasn’t giving air time to my creative side and I needed to do that. I took a sabbatical and enrolled in photography school in Paris and lived out my dream of living in a shoe box in the Left Bank and practicing my French. It was perfect even with the French boyfriend. Nothing lasted long though.

I realized that photography and being a working artist wasn’t in my future, but it was a release valve and I did learn I wanted to incorporate more creativity in my life and work. As I set out to figure out what I wanted to do I started doing freelance with my former hedge fund finance clients. They were either launching new businesses or new parts of their business and needed help with conceptualizing the product, marketing, fundraising and figuring out how to structure it.

As I continued to take on more work I started attracting business from different entrepreneurs across different industries and developed expertise helping start-ups get going. It’s been really awesome and eventually I had too much business; more than I could manage alone, so I incorporated the business and created a team. It’s been interesting and fascinating and it lightens me up. I’m also fulfilled in helping individuals so I took on career coaching as my newest puzzle piece because I can use my skills for maximum impact.

Scott Barlow: Very cool and we will dive into a bunch of that. Particularly Paris, finance, the internships and how you rolled all of that stuff you’ve done over ten plus years into what you do today. Maybe even the Left Bank. Totally squeezing stuff in. When it started and you were taking on the internships what did you think your future looked like? What was your plan? What were some of the internships?

Avery Roth: I’m going back to age 15 or 16 to start. In my family we all had to contribute to the coffers. We didn’t come from a plentiful financial background. I started doing little jobs in middle school. I remember working in a ceramic shop where kids would have parties and paint on plates and jugs. I would oversee the parties. That was my first job that paid like 10-12 dollars an hour. It was fine for my purposes. The owner also let me babysit her kids. So it was two birds one scone.

Scott Barlow: Thank you Lisa Lewis for that one.

Avery Roth: As I progressed through high school I started thinking of professional jobs. My peers were taking on internships. I wanted to explore what my career would look like. I could build on my prior experience. I had built transferable skills. People saw me as being industrious, proactive, and good with people. Some of the different internships in high school I worked for were: The American Cancer Society in their advocacy business and their financial arm. I did a bunch of different things. I didn’t find nonprofits interesting. It was a stale working environment. It wasn’t stimulating, but that could be because I was an intern. I moved then to a cancer hospital and I volunteered in the pediatric unit here in New York City. I guess the link is that cancer runs in my family.

Scott Barlow: I was going to ask if that was something important to you.

Avery Roth: Yes. My mom had cancer and passed away when I was eight. I have always been a huge advocate for cancer research and awareness. I worked at Sloan Kettering in the Pediatric unit. It was hard working with little kids with cancer. Originally I thought I wanted to be a doctor. Spending time in a hospital made me realize it wasn’t for me. The environment stressed me out. I didn’t like the medical smell. I found the environment oppressive. I think these little experiences, like an internship, or working here or there can give you a flavor of what it is like working a place and help you make a decision.

Scott Barlow: Even the smell.

Avery Roth: All your senses come into play.

Scott Barlow: So I was going to crack a bad joke that wouldn’t have been funny. But instead I’ll say that some of those things are incredibly important in life - Paying attention to the things you don’t want and the things you notice are beneficial or helpful to you or give you energy and light you up.

Avery Roth: I think self-awareness is something we aren’t taught or born with. You have to develop it. The more experiences you have the more you can tune into that. You build up a habit of noticing and observing yourself with different experiences. You take data to make smarter choices.

Scott Barlow: On that choices part what made you choose to move into finance? You spent a lot of time there.

Avery Roth: In college I took on a bunch of other internships that paid, in a number of different industries including publishing and advertising. They didn’t stimulate me intellectually and didn’t pay much. Each year that went by I felt disheartened about the world of work.

Scott Barlow: Laughing. I’ve been there.

Avery Roth: Is this all there is? During one job I looked forward to my one hour break so I could go to the park and read “Memoirs of a Geisha.” I had to fight to not fall asleep during lunch hour and hated having to go back to the office. I wanted to shoot myself it was so painful. I identified that feeling starting my sophomore year of college and I’m sure a lot of our listeners are there.

Scott Barlow: Is this really all there is?

Avery Roth: It is so torturous. I remember complaining to my school mates in college about what I would do next summer and one friend suggested trying Wall Street. It pays double, $20 an hour. How exciting! To be honest I didn’t have preconceived notions I was just excited about being paid more. It was a bull market and the firms threw incentives at you. It was exciting. That is how I fell into finance. I got an internship through a friend’s parent who was a trader. I did a one month internship in Boston hanging around the trading floor. I loved the energy and the money. I felt I was constantly learning, which was what I was going for so that is why I chose finance.

Scott Barlow: Interesting. So part of it was falling into it right time right place but once you got there you picked up on things that were good for you.

Avery Roth: A lot of it came down to experimentation. Identifying what doesn’t work and what does to figure out what is for you. It’s like dating. You have to kiss a lot of frogs to find your prince. If you are a princess of course.

Scott Barlow: I was thinking I barely qualify, Alyssa and I were high school sweethearts I got past that, she didn’t have to kiss a bunch of frogs.

Avery Roth: Skip Go, collect $200.

Scott Barlow: Yeah I monopolied it.

So you did the metaphorical kissing a lot of frogs in terms of your career but what happened after that? You got into this role and were liking the vibe. What caused the next change?

Avery Roth: I started my full-time career as a stockbroker advising hedge funds on which stocks to buy and sell. I started my career in London. I did this for about five years moving from one firm to the next for a pay rise and title increase and better client portfolio. I got bored of doing the same thing every day. At least when you are a stockbroker your days are regimented. I would get into the office at 6:45 a.m., not my favorite time, and be ready to advise institutional investors on what to do when the market opens 45 minutes later. You are pushing yourself so hard in the morning getting your ideas together and filtering them down into investment cases, calling your whole list of clients to give them recommendations. The rest of the day you are sitting at your desk, reading research and looking for stock ideas and meeting with clients and schmoozing them.

While at the beginning I found that interesting because news flow was coming at me from different parts of the world, and industries. All sectors have an impact and the different factors you have to track to maintain an investment outlook was interesting. But if you are doing it for five years, focusing on the same markets you are up the learning curve and you just start going through the motions. You don’t feel like you are learning. When I stop learning I’m not as engaged.

I’m going to try and make a long story short. I ended up moving to Brazil because the economies global markets were really strong, which emerging markets are usually stronger. I wanted to experience that and put my money where my mouth was. I moved to Brazil and worked for a hedge fund. I then moved back to London. I had a lot of movement back and forth overseas.

In 2011, I hit a wall because I think similarly to what I mentioned before about exhausting the learning curve, I had spread my wings and learned more and I had exhausted the learning curve of equities and hedge funds. I wasn’t a complete expert but in terms of what interested me I had covered them pretty comprehensively. They didn’t stimulate me like they used to. There was no mystery or satisfaction of learning at a rapid pace. At the same time the financial markets had crashed and institutions weren’t doing well. People were depressed and getting laid off. It was a terrible environment. I thought to myself eh! Peace out!

Scott Barlow: You hit some of these boredom triggers after exhausting the learning curve and at the exact same time there are external factors going on which aligned in an anti-climactic way. What happened next?

Avery Roth: This is when I decided to take a sabbatical and give my spirit some time to soar. I moved to Paris for photography school. My process for getting there was interesting.

Scott Barlow: That was my question. What took place to get to the Left Bank?

Avery Roth: A lot. It’s an interesting thing to focus on because it’s these transitional moments where you are building a strategy out of ambiguity that are learning lessons. It taught me a lot about myself and what works and doesn’t. I left my job, living in London, I bought a bike and was so excited. I rode around singing Oasis really loudly on my bike.

Scott Barlow: singing lyrics

Avery Roth: Exactly. It’s hilarious thinking on it. I also bought a ton of plants because it was spring so I decided to plant the whole garden. I did these excitable freedom type acts and then started chilling out. I went to the cafe where I find my center and can clear my mind and write in my journal and create a framework of what I want my future to look like.

I wrote down all the passions I had that I was potentially interested in pursuing, throughout my life, but primarily what I was interested in while “trapped” in banking. I thought what am I going to do. I let my brain go wild all over the page. After I went through the process of flaring and ideating and mind-mapping and pulling all the ideas out I started thinking through limiting factors. Like financially what can I afford? Geographically where can I viably be (safety, weather)? What if I want to pursue this as a real career? What kind of money can I make? Are there career options? Is it competitive? Could I succeed?

I looked at those factors and filtered down my options to a short list. The two major items left were photography and interior design because I’ve always been into renovating old properties and making them new and architecture. At that point I changed and pivoted my strategy. I went from a strategic framework to a tactical framework. I looked up different organizations that could teach me about these two things to learn more tangibly about what those careers would be like. For example, I went to an interior design school where they bring in potential new students for a day. That free event gave me so much information about what I liked and didn’t. Just being there for a day gave me so much to work with.

Ultimately I decided on photography and needed to create a portfolio. I spent a lot of time creating that and marketing myself for this potential new career. It’s similar to a career change and presenting yourself. I applied to a bunch of different organizations and universities. At that point you have to let the universe deliver what it will. You have a vision, you put yourself out there, and see what the universe delivers. I got into a couple places but went to the school in Paris because I knew it was right. It was a one year program instead of two so I could do it at an accelerated pace which I liked. I had a dream of eating croissants and frolicking around Paris with a cute French boyfriend in a beret. I had to fulfill that dream.

Scott Barlow: I also had that dream, primarily for the croissants.

Avery Roth: Was it as delicious as it was for me?

Scott Barlow: There is a place one of my friend turned me on to saying it was the best croissant in Paris. We ate a bunch of croissants while we were there. I didn’t know how it could be better. We went to this place and oh my goodness, I had no idea. It’s called Ble Sucre. Have you heard of it? Now everyone else has.

Avery Roth: Do they have ice cream?

Scott Barlow: No.

Avery Roth: Okay, not that place then.

Scott Barlow: There are probably lots of places with beyond amazing croissants. This was absolutely amazing. We wrote a blog post about it on familypassport.co. I just gave it away, now everyone will show up.

Anyway carry on: French boyfriend, croissants (mmm the chocolate croissants got me).

Avery Roth: Those are my favorite. I could go on and on but I used to love the hot chocolate and upside down apple cake. I literally tried it in every place across Paris.

Scott Barlow: You are obligated.

Avery Roth: It really was a dream.

Scott Barlow: What is interesting in how you progressed - You went through a dumping process first. After planting, singing Wonderwall, and riding your bike you shook it all out. You filtered and then again and prioritized and matched up options that worked well with what filtered out. I heard that you tested it as well to make sure the options on paper actually worked. Then you started acting on it. Is that a fair summary?

Avery Roth: Excellent summary.

Scott Barlow: I love that because it’s difficult to go from the fuzzy up in the air stuff over to moving to Paris and engaging in photography school. A lot has to happen to get from point A to point Z. You ended up moving to Paris and what happened from there that took you a different direction?

Avery Roth: A few things. I always thought I was a decent photographer but once I arrived in a school where everyone was skilled I realized I was one of the least skilled. That is not to say I could not learn but when I saw the natural raw talent some people had I was blown away. Some of the students had saved up for years to come to this school and they had so much vision and focus that this is what they wanted for their career that when I was there experiencing it I realized I didn’t have the same level of dedication that they did. I couldn’t compete at the same level they would. Not that I wasn’t passionate but I wasn’t passionate enough. I had to get myself in to that situation to benchmark myself. I wouldn’t have realized it from the outside.

I’m glad I did it for a couple reasons. One I always wondered if I was meant to be a creative. At the end of the day I’m a multipotentialite and I have a lot of interests and I’m relatively good at a lot of things but that doesn’t necessarily mean I should be pursuing them professionally. When I turned my hobby into something I needed to do for assignments and getting graded on, oftentimes I was getting crappy grades and negative feedback, not only negative feedback, in France the education system emphasizes criticism instead of encouragement. It’s a different system. It took a lot of joy out of my hobby. Since I left school I’ve pretty much stopped taking photographs, other than just on my iPhone. It took the joy out of it for me.

After the end of the first semester I asked one teacher to get coffee and we went to a cafe and I asked him about job prospects and working with fashion photographers. To get on the map the traditional path was to apprentice with a photographer. I learned from the conversation, which is a good use of my five euros of buying him a coffee, was that there were only a handful of photographers in Paris that would take on an apprentice. They were picky of who they would take on. You had to be French, or you had to have xyz criteria I didn’t have. Even if you got this extremely coveted role you wouldn’t be paid ever. It was the best you could do in your career being the apprentice to xyz. I thought seriously, this is not viable. Not only is it so hard to get these roles but I’m at the bottom of my class and it’s taking the joy out of it for me.

I felt the anxiety building and it comes back to self-awareness. Sometimes when you feel nervous about something it’s your intuition telling you something. I was meant to go through the process to realize becoming a working artist wasn’t for me. I was meant to go to Paris to have the amazing experience but I was meant to move on from it and incorporate creativity in my work in a different way.

Scott Barlow: That is so interesting for a variety of reasons. I think about something we’ve talked a few times about on the podcast in terms of we have so many people that email us questions about wanting to leverage their past experience and combine everything. I think the main driver is we don’t want to feel like we’ve wasted portions of our life. But I think so many of us feel like we have to incorporate those experiences in a way so we are still using that stuff rather than take the learnings from the experience. If that makes sense. You could have said I have all this photography skill set, even though I’m at the bottom of my class, I’m better than the average person how do I jam photography into my life and mesh it with other things. Maybe that is right for some people, but for the average person it is often more what you did, taking the learnings that came from the experience and moving on, and not getting caught up in the sunk cost.

Avery Roth: That is the term I was going to use. The other analogy you can use is like cooking. You have experience making French cuisine and you get burnt out. So you decide to start cooking Mexican food. You get pretty good at it. Doesn’t that mean your next thing needs to be a combination of French and Mexican and the next thing? It would be fusion and confusion! Way too many ingredients. Can you imagine how bizarre that would be?

I’m reading this great book called Essentialism by Greg McKeown, have you heard of it? It’s such an amazing book. The idea is simplicity should be the aim. In simplifying you can maximize the quality of what you are choosing and maximize your happiness in life. Just because you know how to cook French and Mexican food doesn’t mean you should take all, or many, or some of those ingredients and put them together. Maybe you just decide you are amazing at croissants and you are going to pursue them because you love to cook them and everyone loves them and you can make a bleep ton of money selling your croissants and I have so much fun doing it. So I’m going to be a croissant expert.

I think it depends on your situation. Some people love simplifying and some people love having a bunch of different things going on at the same time. It depends on you and your preference. That perspective you are raising about whether prior careers should be considered is a personal thing and it requires a lot of reflection on what you as an individual want and operate best.

Scott Barlow: It’s almost like finding your version of simple.

Avery Roth: That’s a good way to put it.

Scott Barlow: It doesn’t necessarily mean that everything has to be jammed together if your version of simple is you get to be exposed to a variety of things throughout your day or week because that is how you roll and it makes your life good. That’s awesome you should then be doing Mexican/ whatever type of food. Some type of crazy fusion. If your version of simple isn’t that I think it is okay. Taking the learnings and leaving everything else behind is okay. I love that. It might sound weird but I love that you have ditched photography since then because I think it shows a lot of restraint on your part.

It’s awesome that you are on our team so I get to have multiple conversations with you, but when I’m interviewing other people I’m looking for the points where they made decisions other people wouldn’t have made. That is often where the learnings are for the Htycers that are listening. It’s one of the things that most people wouldn’t do. They wouldn’t leave photography behind and be okay with it. Kudos to you.

Avery Roth: Thanks for reflecting that back to me. I think one of the great advantages I had going through this process was I got it out of my system and sometimes when you have the bee in your bonnet for so long the act of getting it out of your system can allow you to move on.

Scott Barlow: Release the bee

Avery Roth: #releasethebee

Scott Barlow: That is going to find its way into training. You need to release the bee. It’s a thing. Hashtag.

Okay, so now what I think is super cool is you take all the learnings you’ve had and help other people do the same thing and facilitate them experiencing these learnings that they already have and putting them together to do something with it like you have in the past. That is what you do which is cool.

Avery Roth: It is so fulfilling. It is so great and I love it!

Scott Barlow: That is a good thing; weird huh? It practices what we preach. Let’s apply it. Want to tackle a few questions? I will read one of them and we can talk through it together.

This comes from Abby in an email. I’ll share her situation and we’ll dive in. She says I’m struggling with choosing between full time careers using analytics. She throws out examples: statistician, HR, business, organizational development, consulting. I’ve loved statistics for a long time. I’m working on a PhD in organizational communication with concentrations in leadership, organizational development, and quantitative methods. I’ve realized I don’t want to go into academia. I love teaching statistics and quantitative methods but can’t handle the amount of social interaction teaching requires. Although I’m okay with one on one. I don’t feel satisfaction with academic publishing and don’t have patience to endure the many months and years the process can take. My struggle with choosing a career in analytics is that there is so much technology out in the world for analytics. I feel overwhelmed and intimidated by it. I know I can learn how to use one or two of the software packages but knowing where to start is difficult to determine. She wants to figure it out. She does some freelance consulting but wants to gain more experience for the long-term to do it more full-time in the future. Knowing that is the long-term goal and knowing what she is facing where do you think she should start and how should she think about it? I will throw out that we don’t know all the details so we can’t give perfect advice but we can help her understand where and how to start thinking about it.

Avery Roth: I guess I’ll start and then if you want to add in your thoughts I’d love to jam. I think there are two things to start with. One she decided she doesn’t want to go into academics and the second is she wants to pursue analytics. I feel like it’s worthwhile perhaps to analyze a bit more why she doesn’t want to do academics. Some of it seems to be perhaps she is more introverted and she is impatient. Taking away some learnings from that would be useful in terms of figuring out her next step and what might suit her. Going with that, and taking the idea that she is introverted and impatient I feel like you can start to build a profile of the type of role that might suit her.

There are a lot of ways you can do more reflection and personal analysis to flesh out your primary attributes and signature strengths but ultimately figuring out what type of role will suit her will help direct her next steps. Let’s say she is introverted and she is relatively impatient, so learning to code could be an option because it is fast moving and introverted but if she is going to learn to code it will determine her next steps in terms of schooling or jobs she might look into. That will be dictated by the roles she realizes make sense for her. I would approach it with the role and apply it to the analytics arena to narrow the field of choices.

Scott Barlow: Absolutely. Building on that when you are saying the types of roles, what jumps in my mind is she has a decent amount of information about what she enjoys but I’d encourage her to push deeper in terms of figuring out why she enjoys them. It will give her clues. Like Avery said, being able to understand what specifically about the educational environment, beyond the social interaction, and trying and figure out if you don’t like the social interaction what are the specific pieces you do like or gravitate to with the information you have. That will give you some of the clues making up the profile of the ideal role or opportunity. That is where, much like you did when you started looking at photography school, you can start making matchmaker. The end in mind goal is doing things that are giving you more experience and reputation before running your own thing full-time. If that is the case I’d push you to clarify what experiences you feel you need to make that happen. What reputation you want to develop. It’s probably not as much about reputation as about relationships. Reputation is easy to manufacture if you have the right relationships. Anything else to add?

Avery Roth: To build on the last point. I think reputation comes with the quality of your work. If you figure out what you are good at and what suits you ultimately you will produce good work and attract business and build reputation organically.

Scott Barlow: In terms of where to start, to sum it up, start with questions of the end goal and what you want, what experience you want, how does it line up with what you know. Dig more into why you don’t want to be in academia and at the same time dig into the whys of what it is you do enjoy because you have good information there. Why do you enjoy it and what is the context in which you enjoy it now?

That rolls right into the next one too. Courtney says I’m struggling to find a career path that compliments my professional and educational background in the environmental field while also providing me something more creative, less technical, and definitely more collaborative. What is interesting is that it mentions what we talked about before. Struggling to find something that compliments her background which may or may not be useful. It may be limiting to try to force it into something that compliments the previous experience. Confusion.

We have this company over here called Corn Fusion so that’s all I can think about. It’s popcorn that is flavored and now I have Mexican food in my head.

Avery Roth: Sorry to ruin that for you.

Scott Barlow: I would say some of the same things in terms of let’s break apart what you are enjoying. Don’t get stuck on the past career path and professional and educational background and focus on the pieces that you enjoyed about the experience. That way you can say should I carry some of that forward and if you enjoy it, and are good at it, absolutely but if not don’t get stuck trying to cram yourself into something that happens to align.

Avery Roth: Building on that if you actually find there are components to your professional and educational background that compel you maybe make a list of the pieces that are creative, less technical, and less collaborative since you’ve highlighted you want to do more of that. Study them and analyze whether there are patterns, trends, and insights about yourself and the type of work you want to do. In parallel you can take time to investigate other passions you have outside of your educational or professional background. Again start looking for different areas allowing you be creative, less technical and collaborative. Build a list, spreadsheet, or mind map of the different elements that you could to that fit those. Ideas will percolate and if you give your brain time to noodle over it and connect dots you may come up with interesting new pathways.

Scott Barlow: This stuff is really difficult. It’s not the easiest. Its critical thought and applying a lot of information in new ways. Give yourself credibility. That is why we created Career Change Boot Camp and do coaching because it is difficult. You and I spent years doing this alone but people don’t have to do that which is why we offer help. So great place to start Courtney and Abby. I appreciate you taking the time to come on and have the conversation Avery. This has been awesome and will be “to be continued.”

Avery Roth: I loved it. Thank you Scott. And thanks to all your listeners. I’m excited to get to know you and help you on your amazing journeys.

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