Building a Career and Business Coaching Firm After Leaving The Law with Ami Watkin [TFLP023]

In this episode, Sarah talks to Ami Watkin, who moved from a big law firm to a mid-sized firm before finally leaving the law and starting her career and business coaching firm. Ami describes herself as a recovering corporate attorney and talks to Sarah about her journey.

Remember, if, like Ami, you want to recover from the grind of the legal profession and move onto a new path, Sarah has a detailed guide on the first steps to get started. Simply sign up on the Former Lawyer website to have the guide sent to you.

Let’s get into the conversation!

Getting Into Law School

Ami never planned to go to law school. She also didn’t intend to work at BigLaw until law school became a plan she could pursue. 

She decided to go to law school in the aftermath of 2008, when it felt like the whole world had come crashing down. She had been laid off from her job doing communications for non-profits while Lehman Brothers went bankrupt, so she was right at the start of this process.

At the time, her friend was in law school and was a summer associate at Cravath, Swaine & Moore. The summer before she was laid off, she spent much time with that friend and her colleagues. 

Since she was as brilliant as these guys, she felt that if she went to law school, she could get a steady job and earn six figures. So, when she lost her job, she thought about how she liked all the people she met at the law firm. Her journey into law began when she was 24. 

From Law School to Big Law

Since Ami went to law school intending to work in a big law firm, it was no surprise that she got into one after graduating. However, she didn’t go into it thinking that she was staying forever or trying to make partner.

Even though she didn’t have a clear vision of her path, Ami knew she would eventually leave Big Law. Still, she felt fortunate to have the job; she took it seriously and worked hard.

Like every first-year associate, she felt like she had no idea what was happening and was drinking out of a fire hose. But she kept at it and continued to make money. 

Thinking of Leaving Big Law

Slowly, the thought of leaving crept in for Ami. The firm she worked at was challenging as she worked in a corporate group that did secure financial transactions, which can get crazy towards the end. She always had to work all night, despite not being someone who did that in college or law school. The new experience was startling for her. 

At some point, she stopped feeling like herself and was frustrated by the lack of autonomy. She slowly started to see that working at a big law firm wasn’t sustainable for her or her relationship with her family. There were overriding forces that she couldn’t fight against to get the kind of work she wanted or maintain a social life outside of work.

While she wasn’t thinking of leaving the law entirely at the time, she knew she needed some change. She started thinking about her move a year and a half after she got to the firm. 

Leaving the Big Law for a Mid-sized Firm

Upon leaving the big law firm, Ami moved to a midsize firm in Manhattan. The firm had a lot of associates who previously worked at big law firms and were now working on mergers and acquisitions for the lower middle market. 

The work pace was more manageable, with sharp and supportive colleagues doing quality work. In that firm, Ami felt like she could catch her breath. Even though her work hours got a little longer when a deal closed, she never had to pull an all-nighter and was often at a loss about what to do with all her free time. 

She thought it was great as she could reconnect with herself and her friends while getting the support she needed to think about the next steps. Ami was happy to have a more reasonable, balanced work-life integration.

Working at a Mid-sized Law Firm

Ami moved to the midsize firm in the fall of 2015. She moved to the firm because she wanted to do more straight corporate work. She did almost exclusively mergers and acquisitions, buy-side and sell-side transactions for privately held companies, and debt and equity financings for business education. 

However, after a six months honeymoon phase, Ami realized that she was not feeling excited about her work as she wanted. She knew that it wasn’t a long-term plan, and as much as she felt happier with her workload and the work culture, she wasn’t hitting her expectations around work, life, and outside work hours. 

A Lightbulb Moment

Upon realizing she wasn’t as excited as she wanted at her job, Ami started exploring her options. She started networking, talking to anyone who had been a lawyer and was no longer practicing. 

Ami wanted to know what they were doing and how they got there. So, she spent time researching and thinking about business development. She thought that she could be successful in business development. 

At some point, she spoke to a businesswoman, who introduced her to a startup and early-stage business attorney. While talking to the attorney, she had a lightbulb moment where she thought she could help small businesses with their legal needs. 

She was also interested in importing artisan work from Mexico and started researching entrepreneurship. Her goal was to start what she called a baby law firm, a solo practice, and then open her small business and see how things went. 

She started creating a plan, saving aggressively, and learning a lot about entrepreneurship to achieve this. She believed that if others could do it, she could succeed too. 

Ami had her last day at the mid-sized firm a day before her birthday in 2017 and hasn’t looked back since then. 

Making an attempt to Network

Sarah was one of the people that Ami spoke to when she started researching her options. She found that Sarah was fantastic and wanted to talk to her.  For her, this is how most of her networking sessions begin.

She describes networking as building connections and communities. Before now, she would feel awkward and uncomfortable at events, but that changed after she decided to give it a shot, especially after realizing that everyone feels terrible about networking.

Now, when she is at an event, she just chooses someone she would like to connect with and talks to them, starting by introducing herself.

However, her preferred approach to networking is more strategic and thoughtful. Here, her first step in networking is to think about the types of people she would love to connect with and then ask her existing network if they know anyone who fits the description and can introduce her. 

Letting curiosity guide her is how Ami ensures that networking stays fun and reduces the pressure of talking to someone new. 

Building a Career and Business Coaching Business

After leaving the law firm in the spring of 2017, Ami took a month off to visit Mexico and get off the grid. Then, she returned and launched her legal practice, Watkin Legal, shortly after.

She learned from that experience that the world would keep spinning and life would continue. Every time she did something terrifying, she got to practice being brave repeatedly. She got comfortable with being uncomfortable all of the time.

Later, she connected with her friend and now business partner, Laena McCarthy, who, at the time, was teaching classes about how to launch a lean startup and bootstrap a startup because that is what she had done with her business and supported many other people in doing the same.

They talked about working together, and after being a guest speaker in Leana’s class, they realized that business people with no legal experience feared the legal aspects of their business. Ami and Leana started brainstorming ways to work together, which gave birth to their firm, Integrated Hustle

The business started by co-teaching classes about how to start a lean side hustle, beefing up that nitty-gritty piece, supporting people in every step of ideation, coming up with a lean business plan, tackling the nitty-gritty, and thinking about where to go from there. As they did that, Ami started networking and connected with a female leadership coach who’d had a long career in business development before moving to leadership coaching. 

That inspired her to consider coaching. After talking to several coaches, especially lawyers turned coaches, Integrated Hustle evolved into a coaching business that helped women execute and grow their business ideas or, if they worked corporate, make a career move to pivot or fly higher in their existing organizations. 

How to Leave the Law 

As a lawyer looking to transition out of the law, Ami advises that it is essential not to feel defeated by the need to figure out your next steps. Instead, you should pay attention to what sparks you a little bit, what lights you up, and what boosts you energetically. When you identify these things, you can start exploring your options.

Also, get support on your journey by joining purposeful groups like the Former Lawyer Collaborative, where you will find lawyers like you who are either transitioning out of the law or have already made the transition. 

If you are looking for personalized support, Sarah, who is the founder of the Collaborative, offers 1:1 sessions where she provides personalized feedback on your process, reviews your cover letters, and holds your hand through it using the Former Lawyer Framework that helps you design an exit strategy that aligns with what your heart wants and helps you find the courage to push through!Secure your slot now by booking a call with Sarah, and you will be on your way to creating the life of your dreams!

Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. On this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let's get right to the show.

Hello, everyone. This week I'm sharing my conversation with Ami Watkin. Ami is a self-described recovering corporate attorney and the co-founder of Integrated Hustle, a career in business coaching firm. Before we get to the episode I want to remind you that I'm offering a free five-day career clarity boot camp starting today, January 13th. There's still time to join, just go to to sign up. I'll tell you a little bit more about the boot camp and what to expect later in the episode, and now on to the episode.

Hi, Ami. Welcome to The Former Lawyer Podcast.

Ami Watkin: Hi, Sarah. I'm so happy to be here.

Sarah Cottrell: I am so excited to have you here. We've talked before and I love your story. Why don't we start out with you introducing yourself to the listeners?

Ami Watkin: Yeah, absolutely. I am the co-founder of Integrated Hustle, which is a career and business coaching firm and I am a recovering corporate attorney.

Sarah Cottrell: Woohoo! And how long have you been a recovering attorney?

Ami Watkin: I would say I have been in a Biglaw recovery for about two and a half years now. I do still have my own small legal practice where I work with a select number of clients in creative services but I left the world of Biglaw in Midtown, Manhattan in Spring 2017.

Sarah Cottrell: Got it, okay. Let's go all the way back to before you went to law school. Did you always know that you wanted to go to law school? Were you always thinking Biglaw? Tell me about all of those things.

Ami Watkin: Yeah. The short answer is no. I was not always planning to go to law school. Until law school was on my radar as a career path certainly, I spent no time thinking about Biglaw. But I decided to go to law school in the aftermath of 2008, which as you know, is when it felt like the whole world came crashing down. I got laid off from my job doing communications work for non-profits and this was literally at the same time when Lehman Brothers collapsed, so at the very beginning of this process.

A really good friend of mine was in law school at the time and had been a summer associate at Cravath, Swaine & Moore the summer prior to all of this happening and I'd spent a lot of time with her and her colleagues over that summer living the great luxurious life that comes with being a summer associate.

When I lost my job I thought, “Well, I really liked all those people and they were really smart and I'm smart. If I go to law school and do really well, I can get one of those jobs and earn six figures.” So began my path into the law. It wasn't a full-on impulse decision but it was somewhat impulsive and reactive based on my circumstances and how I knew to help myself at the ripe old age of 24.

Sarah Cottrell: Yes, with all the years of accumulated wisdom that a 24-year-old has. I graduated from law school in 2008 so I'm familiar with the whole downturn also but in the sense that our law school class was the last year that went through a typical summer program hiring process and then it was those next couple years after that, I've had a couple people on recently who graduated in 2011 and we've talked a lot about the challenging legal market in those years.

You didn't always think that you would be a lawyer, but when you did go to law school I guess it sounds like you basically were thinking that Biglaw was going to be your path. When you graduated from law school, did you already have an inkling of “Hey, maybe Biglaw was not going to be for you for the long term”? Or were you more gung-ho like, “I'm doing it, six figures”?

Ami Watkin: Both I would say. I will say I never went into Biglaw with the intent of making partner and staying in forever. I never thought that was going to be my path and I can't say that I had a clear vision of what I thought my path would be, but I just knew that eventually it would involve not being in Biglaw. I did go in fairly gung-ho. I felt really, really fortunate to have the job that I had and I took it really seriously and I worked really hard.

I, like every other first year associate in the entire world, had no idea what was happening and basically felt I was drinking out of a fire hose, but I kept at it and I was really proud of myself for getting the job that I had intended to get and grabbing that brass ring. It was yes-and, both-and.

Sarah Cottrell: I am familiar. I think that is for sure a common story, especially I think there are a lot of people who go the Biglaw track who maybe don't necessarily go into it thinking like, “I want to make partner,” but their idea about what their alternate path might be is a little bit fuzzy like, “I'll work as a lawyer in some other way,” or at least that's how it was for me coming out of law school. I know that's true for quite a few other people.

At what point when you were at the Biglaw firm did you start to think, “Maybe this is really something that I want to get away from”? And potentially a different way than you had been thinking about at first.

Ami Watkin: Yeah. I would say it happened really slowly. It was a challenging environment out of the gate. I was working in a corporate group doing secured finance transactions which are inherently not that crazy and then totally crazy towards the end. I very rarely got through one of them without an all-nighter close to it which was the first time I'd done that ever. I was not someone who stayed up all night for work purposes ever in college or in law school so this was a new experience for me.

But I just at some point stopped feeling like myself. I was frustrated by the lack of autonomy and what I felt like were overriding forces that I couldn't push back hard enough against in terms of getting the kind of work that I wanted or feeling able to maintain the social life that I wanted outside of work, the canceling plans, or ending up at the office super late, what have you. It crept in slowly and I would say it was in talking with family that I just started realizing, “Yeah, this is not something that's sustainable for me in this way.” I wouldn't say it was leave Biglaw, go do something else, but I knew from there I needed to shift gears in some fashion.

Sarah Cottrell: Yes. First of all, I also pulled my first ever all-nighters in Biglaw and had never done that before in college or law school because I am not a night person and I was like, “How did I avoid this until now?”

Ami Watkin: It's rough.

Sarah Cottrell: And it was terrible. How long had you been at the firm when you had this realization and talking with your family?

Ami Watkin: I think I'd been there about a year and a half because I left my first firm at almost exactly the two-year mark, so probably a year and a half in, I started thinking I've got to figure out how to make some moves from here.

Sarah Cottrell: When you left, where did you go?

Ami Watkin: Yeah. I left, I was at DLA Piper, which I have so many amazing friends from DLA, and while my personal experience there was challenging, I think because I would have had a challenging experience in any Biglaw firm, I have so many amazing connections that came out of DLA. I want to give a shout out to how wonderful it was in that respect. I left there and I went to a midsize firm in Manhattan that was about 125 lawyers all in and only in New York.

It's a lot of Biglaw refugees and we did a lot of mergers and acquisitions for the lower-middle market. It was a much more manageable pace. The work quality was really high, the attorneys are amazing there, they're incredibly sharp and supportive, and it was a place where I could catch my breath.

Sarah Cottrell: I think that is really important and it's something that I've talked with a few guests about this idea how, a lot of times, people when they're unhappy as lawyers and even people talking about making career changes, there's often this all or nothing mentality of “I'm going to stay forever and just hate it and that's just how it is, or I'm going to quit right now and who knows?” There's actually a lot of middle ground, and in particular, like you were saying, finding something that gives you a chance to catch your breath, think, and make a more thoughtful choice about the next thing that you want to do I think is something that is definitely worth considering.

I understand for sure why people have this sense of, “Well, I just want to know what the next thing is.” I completely sympathize with it because I've been there. But I think having that space is so helpful. It sounds like that was definitely true for you.

Ami Watkin: Oh, yeah. It was wonderfully luxurious. I remember starting and of course when a deal closed and stuff, the hours got a little longer but I don't think I ever fully pulled an all-nighter. I think I came close maybe once in a very extenuating circumstances there but I left every day around 6:00 or 6:30. I remember thinking, “What am I going to do with all this time? What do people do who get to leave work at this hour of the day?” and thinking my phone might be broken because I wasn't getting emails at varying hours. It was great. I got to reconnect with myself, with my friends, get the support that I needed to then even begin to think about what could come next.

Sarah Cottrell: When you went there, were you thinking that it was probably a medium-term thing or were you thinking maybe this is where I'm going to land long term?

Ami Watkin: I honestly don't think I really knew. I was really happy to be into a more reasonable work-life integration, balance situation and just thought I'll see how this goes. Like I said, I never had any dreams of becoming partner anywhere so I can't say that was top of mind. But I didn't go in with “I'll be here for two years and then I'm out” type thing. It was much more organic than that for me at the time.

Sarah Cottrell: That makes total sense. I guess first I should ask what year was it that you made that move?

Ami Watkin: Yep. I moved to the midsize firm in the fall of 2015.

Sarah Cottrell: From 2015 to now, tell us everything.

Ami Watkin: All of the things. One of the big drivers beyond wanting a better work-life balance in making the shift from Biglaw to midsize law was also wanting to do more specifically straight corporate work. While I was at the firm, I did almost exclusively mergers and acquisitions, buy and sell side for privately-held companies and debt and equity financings for emerging companies. I got a really to experience the life cycle of a business in a really different way because when I was at the first large firm, I did almost exclusively secured finance just because that was what was there. I dabbled in M&A but it was hard getting my hands on more of it.

I would say I got a bit of a business education in a lot of ways while I was at the midsize firm. After I'd say about a six-month honeymoon period, it became clear to me that no matter how I dress it up, working within a firm and doing this deal work, even though it was lower-middle market, so it was a more human scale in the spectrum of big, still didn't feel super human to me. I just knew this isn't going to be it for long term. I just trust in my gut. I was much happier in terms of my workload and the culture around me, in terms of the expectations around work and life and life outside of work, but I just knew it wasn't quite right.

So I started exploring. I can't remember if we talked about this but I'm really the only person I really know who really likes networking and I went after it and I went after it hard. I started talking to anyone who would talk to me who had been a lawyer and was no longer a lawyer and wanted to know what they were doing now and how they got there. I just started researching and I thought about business development. I spoke with people at a number of really amazing companies doing biz dev and thought that I could be successful in that but it didn't really feel resonant to me.

I just kept exploring, digging, and gathering information, bringing it back, holding it up against myself, trying to identify what I really wanted, and then keep hold of that vision and just started sifting and triaging through various options. At some point, I spoke with a woman named Johanna Peet who has an amazing skincare line called Peet Rivko. I think she was pre-launch at that phase. I spoke with her and she told me that she had this wonderful attorney who worked exclusively with startups and very early stage businesses.

I spoke with her and her name's Agatha Kluk. She has a really amazing firm in New York called Kluk Farber. She works with, I’ve described it as every cool girl downtown brand in New York. She has an amazing business that she's running and firm that she's running. I spoke with her and at the time she was a solo practitioner. I can't recall if she'd had taken on a partner. I think she might have still been on her own.

We talked about her evolution into that space and how she started by working as a “freelance” attorney. She would help people with their legal needs, do it for small businesses, and everything from formation and setting up your legal foundations and household, to negotiating commercial contracts, and all that stuff. I had this light bulb go on above my head where I thought, “Oh, well maybe I could do that. Maybe that would be a better way to be a lawyer.” At the same time I had this long-held vision of starting a business, importing artisan goods from Mexico.

That was another thing that I was really interested in exploring as well. I've Loved Mexico since forever. I've spent a ton of time down there both living, working, and traveling. I thought, “I'm going to try my hand at opening my own little what I called a baby law firm, a solo practice, and then open this little business, importing some artisan goods from Mexico and see how things go. I'm just going to see how it goes,” which I'm realizing as I'm speaking is the running theme of how I approach things. “I'm going to try this and see how it goes.”

I started creating a plan around that. I started saving really aggressively and I just started researching around entrepreneurship. I listened to tons of episodes of how I built this and on being and just anything that felt inspirational and gave me courage and hope that I could borrow from other people. I just kept thinking, “If all these other people can do it, I can probably do it.”

Fast forward to, I would say, I shared this news with my parents around Christmas 2016, and made a plan for when I would leave the firm and what that would look like. I gave my notice in April 2017 and I had my last day the day before my birthday, if I'm remembering correctly, and started a whole new life on my birthday in 2017 and never looked back.

Sarah Cottrell: That's awesome. That's so cool. Also though, can we go back and talk about how you liked to network? Because I think that's an amazing life skill that very few people have. I certainly would not describe myself as someone who likes to network. Can you tell me a little bit more about why you like it? I imagine since you like it, you're also good at it. That seems like a fair assumption. I'm sure there are lots of listeners who either want to be doing networking, need to be doing networking, are doing networking and maybe could benefit from some thoughts from someone who loves networking about how to network.

Ami Watkin: Yeah. I'm happy to share. I guess I'll start with you. Because I reached out to you cold and now we're here. That didn't feel gross or yucky and transactional though. It didn't for my end. It was like, “Wow, Sarah's so awesome and I want to talk to her,” and I would say that's how most of my networking attempts begin.

Sarah Cottrell: I like it. I think in my mind when I hear networking, I think like bar association cocktail party. Do you know what I mean?

Ami Watkin: Yeah.

Sarah Cottrell: Maybe I need to expand my mental definition of networking.

Ami Watkin: Yeah. I think you hit the nail on the head. I think about networking as just connection building and community building. I, like you, when I go to a bar association networking event, I'm not real happy about it. It's not my favorite way to meet people or spend my time. I think that's really common. I think that's 100% universal. I'll never forget when I was post-2008 and pre-law school working at another PR firm and I was at an event with my now dear friend, Amanda.

A client told me to go talk to someone about her new book. I turned to Amanda and I said, “How am I supposed to go talk to this person?” We were at this really incredible cocktail party in a penthouse of the Bloomberg building and it was bananas. I was 25 I think and feeling way, way out of my league. She said to me, “Everyone feels uncomfortable doing this and everyone feels awkward. So how you feel is how everyone else feels so just give it a shot.”

I thought, “Oh, if everyone feels terrible doing this, well, that makes me feel a little bit better.” That felt really empowering and I think I did give it a shot. I think it was really awkward and weird and not a particularly successful encounter, but it stayed with me. In any sort of event like that, I just accept that everyone feels awkward and weird. I think, “Well, who looks like someone I'd like to speak with and connect with?” and I take it from that angle and I just say, “Hi, I'm a me,” and then they usually introduce themselves and then we go from there.

It's a pretty simple approach. But it's not my preferred way of networking. What I really like to do and what I work with my clients on doing and teach others how to do or to do is to be much more strategic and thoughtful. Because you don't know anything about the people who are in the room at that event and if there's 100 people, it's a very arbitrary process in terms of how you connect.

What I tend to do is think who are the kinds of people I'd like to speak with, whether it's people who are working in a specific area, who are living in a certain place, who have traveled to a certain place, who have done something that I would like to know about, and then I activate my existing network, which is anything from friends and family to an alumni networking page to LinkedIn and I say, “Hey, does anyone know a person who fits the bill?” I made a lot of queries of my friends when I was doing my early stage research about, “Hey, does anyone know any people who are attorneys who are no longer attorneys? If you do, would you make an introduction?”

That got me to my first few people. Then I realized there was this common theme of business development. Then I think I did another round of “Does anyone know people who work in business development? I'd love to learn more about it.” Then I got connected to people that way. Then at the end of each of those conversations, I say, if it's been a good conversation and it's felt rich, dynamic, and fun based on our conversation, “Is there anyone else you think I might benefit from connecting with?”

If they offer to make any additional introductions or say, “Let me think on it. Would you mind following up with me?” I said, “Of course,” and I follow up and I go from there. It's a much more targeted approach and I find that to feel a lot more organic and a lot more genuine for me. I am naturally pretty curious and I really like learning about what other people do and what their stories are. I think that's how I've landed in this work and why I find it to be so much fun. Really, I let that curiosity guide me and drive me and that's how I make it fun. There's no pressure attached to anything. It's purely a fact-finding mission and investigation.

We'll get back to the episode in just a few seconds, but first, a shout out to this episode's sponsor. This episode is sponsored by possibly the most important free training I've offered yet. On January 13th through 17th, I'm offering a free 5-day Career Clarity Boot Camp. Do you know that you don't want to be a lawyer but have no idea what to do next? I've got your back. During the boot camp, you'll learn exactly what you want from your career and the next step that you need to take. The best part, it'll take you less than 15 minutes each day and you won't be doing it alone. I know what it's like to be totally at a loss for what to do next when you realize that you don't want to be a lawyer. I've been there. It turns out the process for figuring it out is deceptively simple. Get super clear on where you need to go next without the overwhelm. Go to to sign up today. Now, back to the episode.

I think that's really helpful. I think it connects somewhat to one of the things that you mentioned a couple minutes ago in our conversation which was, I can't remember exactly what you said but it was something about how you made this decision to make your next move and you essentially assumed because there were all these other people who you saw who'd done similar things that you also would figure it out.

I think that there is sometimes this perception, particularly from lawyers just because of our training that the people who make a move and do something else have some special knowledge or only made a move because they were completely sure that that was the thing that they should be doing. I think it keeps people from making decisions that would improve their lives and careers because they think that they need to have what they imagine the level of confidence is that someone else who left had.

In other words, in the same way, you're talking about networking and talking with people to figure out what you want to do and I think even sometimes with networking, people think that what they need to do is sit in their office, just think really hard and figure out what they want to do, and then find the one person who can connect them so that they can go do that thing as opposed to seeing it, like you were describing, as more of an exploration.

One of the themes that I've seen in just all the different people that I've talked with both on the podcast and just in my regular everyday life is that most of the people who make a big move out of the law approach it more in the way that you're describing in terms of exploration, “Hey, I think this thing might be the next right step so I'm going to take it and work from there,” as opposed to having this, “Well, now I've set out this new path and this is the path I'm following and I will not deviate from the new path that I have now decided is the path that I should be on.” I think that that is really helpful and important.

Ami Watkin: Yeah. I think you're raising something that I didn't say explicitly but that you're pointing out and that I definitely felt which is in networking and in all these conversations, it was a great opportunity to start building the muscle of courage. Because every real person who I spoke with and connected with who had made some big move was another data point that it was possible versus the people you read about but who you don't really connect with. The more I was able to humanize that process and make it tangible and grounded in reality with people who I was sitting across from, the more possible it felt and became.

Sarah Cottrell: I think that is super helpful and in fact I think the episode that released this week the week that we're recording, I am pretty sure we had a very similar conversation about gathering information which gives you this sense of it being possible but also builds up your own confidence.

Ami Watkin: Yeah, you did. Actually I'm halfway through listening to it and you totally did.

Sarah Cottrell: I was like, “I think that was this week.” For anyone who's following me on social media, I know that you know that we just moved, so having moved across the country, everything is a blur. So Spring 2017, you decided to strike out on your own. Talk to me about what happened next and also about your business Integrated Hustle.

Ami Watkin: Yeah. Spring 2017, I took a little break, I went to Mexico for a month and treated myself to time off the grid. Then I came back and I launched my legal practice, Watkin Legal, shortly thereafter. I would say that was an exercise and just learning the same lesson over and over again, which is you do something that seems terrifying, the world keeps spinning, you continue to live and breathe, and then nothing catastrophic happens and you keep going, and then you do something else that's scary.

It just was the space where I got to practice being brave over and over again. I remember the first time I sent an email announcing that I had opened my doors for business, my virtual doors, and just how scared I was to push send on that distribution in MailChimp. Now I think, “Oh, whatever.” No, like, “Oh, that's a thing I can do. That doesn't feel scary at all anymore,” and then it was so scary. I remember reaching out to my girlfriends for a pep talk before I did it.

I just got comfortable in being uncomfortable all of the time and I got used to that. Then I connected with my friend and now business partner, Laena McCarthy, and it started because I realized she was teaching these classes at a place in New York called the Brooklyn Brainery about how to launch a lean startup and bootstrap a startup because that is what she had done with her business and supported many other people in doing the same.

We talked about joining forces and I was the guest speaker at one of her classes, it was a four-part series, to talk about legal 101 and what it takes to get your house in order, which we now call the nitty-gritty, things like what is an LLC, what's an EIN, how do I figure any of that out, how do I form one. That's a general reaction that we found from basically all non-entrepreneurs, existing entrepreneurs, and non-lawyers, everyone, this is the stuff that scares them.

Laena and I had a lot of fun and we started brainstorming about other ways we could work together and iterate on that first class. Integrated Hustle was born by co-teaching classes about how to start a lean side hustle, beefing up that nitty-gritty piece, and supporting people in every step of ideation, coming up with a lean business plan, tackling the nitty-gritty, and thinking about where to go from there. As we did that, I started networking, surprise, surprise, and connected with a woman who is a leadership coach and who'd had a really long career during business development and then pivoted from that to leadership coaching.

It was a moment where a light bulb dimly went off above my head and I thought, “Huh, that sounds really cool. Maybe I would like to do more of that. I wonder what this is. Can I build a career off of this?” I did what I do and I started reaching out to other coaches and other lawyers turned coaches and finding out more about what this whole world of coaching really meant and what it really looked like. I was doing that in parallel alongside refining our offerings for Integrated Hustle and we started thinking about other things that we could do, teaching classes about networking.

I was really also interested in exploring both leadership coaching and career coaching because I had had and continue to have this winding career path and I realized that the things that I really love to do are build relationships with people and help them tackle things that seem somewhat insurmountable or really complicated, parse it out into its base elements, and figure out how to tackle them one-by-one so that it's manageable and it's just consistent action over time. I realize that that's where my natural strengths really lie.

Integrated Hustle was this organic evolution of first teaching women how to start their own side hustle businesses and then expanding beyond that to offering business coaching. Once you're launched, where do you go from there? How do you continue to grow? How do you continue to think about the big picture, expand your horizons, continue to take action? Because as you know, I'm sure too, actually forming the LLC and getting the EIN are the easy part.

It is the actual execution and growth of a business that is the real challenge, so we focus there and on working with leaders who want to do one of two things, which is either rise higher in their existing role, if they are one of the lucky ones who found where they want to be and feel really integrated in their existing organization or path and want to figure out how to fly higher, or if they want to make a career move, they've had that moment just like you and I had of “This just isn't the right thing and I've got to figure out what is,” and that's a really daunting process and so how to navigate that process too?

Integrated Hustle is the result of all of those interests and really a shared sense that Laena and I had of not having these resources and access to this support when we were making the moves that we made of launching our businesses, making tough career decisions, and really forging ahead alone with the support of friends and family but no one else who’d walk that path in front of us. It was really a shared desire to create resources and services that would support women who are navigating those same paths and really who feel committed to aligning who they are with what they do every day.

Sarah Cottrell: Yeah. I think that the challenge of breaking down the component parts of what you need to do in order to figure out, well, I'm thinking specifically of obviously lawyers, what you need to do in order to leave is, I completely understand why it's daunting because, like you said, I've been there and you've been there, and I think also it's much more complex than just, “Well, law didn't work out for you so figure out what the ‘correct’ thing is that you're supposed to be doing which isn't law but is something else and then go do that.’” There's a lot of, and I suspect you would agree, deeper work that you have to do, and certainly there's also practical things like financial aspects and those sorts of things.

But also trying to figure out what you should be doing with your career touches on almost every aspect of who you are and your life. I think working through that can be obviously extremely complex. Actually two-part question, because I was going to ask this earlier, when you were making your transition out of the firm, I think that you said that there wasn't really anything like what you are offering with Integrated Hustle, but did you work with any coach, therapist, or anything like that?

Because I know that there are people listening who are trying to figure out what's their best path forward, and then what type of work are you doing in terms of are you doing one-on-one, do you do group stuff? I think it would just be really interesting for people to hear a little bit more about the logistics of how you provide that kind of support.

Ami Watkin: Yeah. To travel back in time, I did work with a career coach for a while. It was not the best of experiences. I had a really great time with her when we were actually in sessions and then dealing with her otherwise was very difficult, shall we say, she shall remain unnamed. That was one of the things that I thought I spent quite a bit of money on working with this woman who really felt super unprofessional to me and was just not aligned with the standard that I felt was reasonable for the amount of money that I was investing in her. It was helpful but it was not the be-all end-all.

I will wholeheartedly say, I definitely learned some things about myself and got quite a bit of clarity on a lot, but it wasn't a super positive experience. Then I did find a really great therapist who really supported me in that really deep emotional work that was tied up in who am I if I'm not a lawyer, this has been my identity for quite a lengthy period of time now, and how do I figure out how to navigate this new unknown space?

I personally think that if you have the resources and are able to do it, therapy plus coaching, working with a good coach who really is a fit for you is a pretty magical combination because the therapy supports the more emotional side of things and the thinking about how to heal things that happen in the past to be in a position and move forward and then the coaching takes over from the present moment into the future and helps you keep acting from that new more evolved emotional space if you will.

I did have support in that way and then in terms of how I work with people on that, I would say that we offer small group coaching workshops, one-on-one coaching is the place where I really love to play because I think it does create the room for doing that deep work that you mentioned. It's really about saying where you are is exactly where you're supposed to be and then figure out where you want to go, and really being open to getting messy and being committed to the process.

I really work with my clients to support them in their process, whatever that looks like for them. What works for them may not work for me and vice versa. I really partner with clients to figure out what fits their life right now, today, in this moment, what's important right now, and recognize that that is probably going to change over the course of not just our work together but over time, and how do you adapt and evolve as you learn new things, gain new insights, and then are able to take new actions, and how do you just keep that ball slowly rolling forward.

Sarah Cottrell: Yeah. I think that is really insightful and you are not the first person on this podcast to say therapy plus coaching. This is also a very common theme. If there's someone listening and they are just like, “I am done with being a lawyer but I don't really even know where to start,” or even if they're thinking like, “Well, I don't love this job. Maybe I should be doing something else,” what kind of advice would you have for people who are listening in those positions?

Ami Watkin: I think the single best thing for anyone to do in any position, legal or otherwise, though clearly it's probably mostly lawyers listening here, is to instead of feeling defeated by what do I do next and how do I figure this out, is to just start paying attention to what sparks you a little bit, what lights you up, gives you a little boost energetically. What are the parts of the day that you look forward to? What are the things that you do that are energizing? It does not have to be within the purview of your work day. It could be something you do outside of work. It could be something wholly unrelated to your professional pursuits between the hours of nine to five.

But I think it's just really important to pay attention to what's giving you that boost and start exploring there. It's really helpful to bring a little notebook, buy yourself a new small portable notebook that you'll actually carry around and just write down things that you notice and start keeping track. I think that gives you really amazing data to work from. When I think back at my time within the law firms, there were things that were incredibly challenging and there were things that I really loved.

The things that I really loved were building relationships with my colleagues and building relationships with my clients, having the opportunity to mentor and support people who are climbing up the ranks behind me to try and help them have a better experience than I did, working with some of the staff who are young and trying to figure out what they wanted to do next and were working as a paralegal but that was a stopgap measure.

There were moments that would really spark me throughout the day and that was a place to start paying attention. What am I gravitating towards and what am I gravitating away from? Then use that as a place to start having conversations around and looking for people who spend their times doing those things that are exciting to you and start researching there.

Sarah Cottrell: I think that is really good advice. Ami, is there anything else that you would like to share that we haven't talked about yet or anything else that you think the listeners of the podcast should know?

Ami Watkin: Yes. In addition to coaching which Laena and I do on both the business, the career, and professional fronts, we are launching a product in the new year called The Startup Kit, which is a nod to our OG roots of supporting women in starting lean side hustle businesses and it is a one-stop shop for digital, it's a digital product that really walks you through not only the nitty-gritty that I referenced, the basics of what is an LLC, what is a corporation, what's an EIN, how do I get them, what do I even need a lawyer for? Coupled with bespoke lean business plan template to really help you ideate and think about things in a more holistic big picture fashion and a step-by-step guide to networking that walks you through the literal steps that I take to build connection and community and the approaches that I use to make it work for me and some offerings of how it could work for you. It's a one-stop shop for how to research and launch a lean side hustle business.

Sarah Cottrell: That's awesome. People who are interested in connecting with you or learning more about that product or the other things that Integrated Hustle does, where can they find you on the internet?

Ami Watkin: Yes, come join us, you can find us at and we have a mailing list there where you can receive a free guide to finding your own superpowers, those things that light you up, and you can follow us on Instagram @IntegratedHustle and on LinkedIn @IntegratedHustle. For people who sign up and join our community, we're also offering access to a private Slack Channel where you can bounce ideas around with us, ask us questions, and get responses in real time in a more closed environment.

Sarah Cottrell: I love that. Ami, thank you so much for coming on the podcast today and sharing your story. It was really great to talk with you.

Ami Watkin: It was a total pleasure. Thank you so much for creating this community and the opportunity for other people to borrow all of our collective courage and hopefully learn from all of your wonderful guests.

Sarah Cottrell: Thanks so much for listening today. I absolutely love getting to share these stories with you. If you haven't yet, subscribe to the show, and come on over to and join our community to get even more support and resources in your journey out of the law. Until next time. Have a great week.