Today we sit down with Skylar Romines, founder of ATW Advisors and author of So She Did. In this episode, Skylar shares her 17-year journey in commercial insurance, how she built a thriving consulting firm, and the challenges she faced transitioning from corporate America to entrepreneurship. We dive deep into career-building strategies for women, the importance of networking, personal branding tips, and how to overcome work-life balance struggles. Skylar also reveals how she cultivated her successful personal brand on social media, particularly on Twitter, which helped her land clients and grow her business. Perfect for aspiring entrepreneurs, women in business, and professionals looking to level up in their careers.
To connect with Skylar Romines, follow her on Twitter at @SkylarRomines or find her on LinkedIn under Skylar Romines.
Check out her book So She Did available on Amazon!
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Listen to the podcast here
Making The Switch From Insurance To Entrepreneurship
In this episode, we’re sitting down with Skylar Romines. I had the opportunity to read the book that she published called SO SHE DID, which is about strategies for women engaging in the workplace. It’s great to have you out. I’d love to hear a little bit about your background first.
Introducing Skylar Romines
Likewise. Thanks for having me on. I’m excited. My background professionally is mostly in the commercial insurance space. I spent several years of commercial insurance brokerage outside of a few years working exclusively with a captive group based out of Dallas. The remainder of that time was spent in the brokerage world so commercial insurance broking. Pretty much exclusively, I started with construction firms and then moved more into commercial real estate and development. I have been in that space for over a decade focusing foot wide mile deep type of focus.
I left the commercial insurance brokerage world to launch my firm, which is ATW. It is essentially an insurance consulting firm. We’re calling it the owner’s insurance rep. It’s a bridge between our clients and their brokers. Since the insurance space has been so challenging for certain people in the last couple of years, it felt like the right time to make that leap. I finished writing and publishing my first book SO SHE DID. It’s helping new people, although specifically geared towards new women. It has some useful information for anybody new to the workforce like how to build your career and how to leverage things like networking and personal growth and development.
Writing So She Did
I was going through the chapters with the specific points of advice and you had two stories for each chapter. How did you find and identify? What was the process of interviewing the women in your stories?
This is one place where I’ll say I screwed up. If you’re a first-time author and you want to include stories from someone in your book, learn from me here because I learned the hard way. I went through the process of writing about 80% of a book. I knew at some point I wanted to leave people’s stories in but I did a ton of research, had a lot of stats and my viewpoint, and had essentially finished a book. I thought for some reason that I’ll find some people and their stories will naturally weave into what I’ve already written.
What I did was reach out to my network. It’s people I’ve worked with in the past and some groups that I’m a part of like CREW Orange County, which is Commercial Real Estate Women of Orange County. I asked people, “I had a list of categories. Do you have either one specific story about an event that occurred or does your background in some way fit into these narratives essentially? If it does, would you like to share it? Were you a working mother who transitioned to the workforce? Did you have this or that? What challenges did you overcome? Are you willing to share them with me and my audience?”
I’ve been taking down notes and doing research for so long that it was eating up my time. This was during early COVID. I had extra time. I’m a person who always needs a side project. This was my side project but it got to a point where I figured, “You either do something with it or leave this thing alone.” I don’t know what this thing is and it’s taking up too much time and energy.
I put it out in my mind where I was like, “I need probably 20 or 30 women to share their stories. If I don’t hear from 20 or 30 women in the next week, I’m going to leave this project alone and move on to something else.” There were 36 women in the first 2 days who reached out to me. They’re excited and looking forward to sharing their stories. By the end, it was about double that before I took the post down in 1 week or 2.
What that taught me was a lot of people have stories that they’re excited to share, which is fun. What I did was over the subsequent few weeks, I interviewed all of those women, some in person and most of them on Zoom. I gave everybody about an hour to share their story. What happened is I realized that the whole book that I had before needs to be rewritten.
It was full of my thoughts and viewpoints. I have one thought process and I’ve been through my story. I tried to share a lot of different viewpoints but at the end of the day, I still only have my viewpoint. We can’t get out of our biases beyond a certain degree. A lot of women are a lot further along in their careers than I am. We had one woman who was on Wall Street in the ‘80s who shared her story with us for the book, which I thought was extremely interesting.
Up until the end, I had two versions of the book going where one was this initial version that I had. I woven some stories into it. There were only a few and it was mostly my viewpoint and a bunch of statistics. I had a version of the story where it’s what you see, which is a lot of women sharing their stories with a little bit of my voice mixed in and a few statistics.
For a time, I liked the other version better but the feedback I kept getting was people wanted a Chicken Soup for the Soul for business. They were interested in reading the stories versus having the sets that back them up. Ultimately, I decided to go with that version of the book. My advice to anyone who’s looking to write a book is don’t put yourself through the mental ringer like I did. Interview the people you want to be a part of the book upfront so you know what you’re working with and write around it versus trying to weave that into your story.
Career And Motherhood
That’s super interesting. The story that stuck out to me the most was Christina, who was going back to the workplace after seventeen years. To me, that is the biggest structural barrier we’ve got going on. The breaking point is with 2.5 kids, it doesn’t make sense to have a person go to daycare. You’re paying for daycare. To me, that’s a huge structural hurdle. Go deeper a little bit into the book. How did she overcome that mental barrier? I can’t think of any person who would not have that mental barrier, male or female, seventeen years or not.
There were a few things about Christina in particular that stood out to me. She’s a go-getter in general. There were some innate personality skills that made her suitable for the workplace. Those are also things that make her a great mom. That was one thing that I wanted to pinpoint in the book. I don’t think it’s exclusive to women but we do hear about more women staying home and raising children still, even though that’s starting to shift a little bit.
It’s exceedingly difficult to show, “I’d been a mom for seventeen years and I would also be good at running your company for you.” There are so many transferable skills but they’re not necessarily easy to quantify on paper. Especially when you have multiple children, you’ve stayed home with them for that long, and helping support your husband, you have to have organizational skills. You have to be able to manage a team.
You’re managing a team of little people but those can often be more difficult than a team of big people. A lot of the same challenges come into play because people get older. They may not pitch a fit the way that a toddler does but you still have to manage all the personalities and different interests. There are a lot more transferable skills from parenthood to the business world and vice versa than a lot of people recognize.
The other thing that Christina had that helped her build that second chapter in her life, if you’ll call it that, is a great support system. She ended up working for a company, which was essentially family office-based. It was a family-run company. As soon as they met her, they had a good feeling about her and decided to take that chance on her, which is a huge thing. Without someone deciding to take that chance on her, it would have been incredibly difficult for her to find a role that paid well.
The other thing that she had was an incredible husband who had been working for that entire period in their lives, had always been the breadwinner, and had no hesitation or doubt. She shared with me that she was the one who initially had more doubt. “Can we do this? Can we swing this with me going back to work? Do I need to stay home and be the one who supports you here?”
He told her, “I want you to be the most fulfilled version of yourself. If that looks like you finding a career outside of the home, we’ll find a way to make that work. Our kids are old enough.” She didn’t do it when her youngest was six months old. She waited until they were all in school but she had his full support. There were a couple of other women in the book who had a similar thing. I realized their situation would not have worked or would have been much more challenging. They would have had to carry a much heavier load had they not had that supportive partner. That made a difference for her, too.
My partner is in San Antonio and I was in New York all week. I flew down here to tape this. We’re starting to have whispers about a second trip for little ones. The dynamics of that, even in my head, are complicated at best.
It’s a challenge. You can do it. We see people who make it work. It’s a challenge to keep a relationship going and both have careers. You add in the additional layer of having little people running around. There’s one more thing to worry about but it can be done. You guys will be awesome at it. People think about it ahead of time and plan. Not that you can plan everything because you’ll have your best-laid plans. When kids get involved, it is out the window anyway.
A lot of people are making it work. If someone decides they want to stay home and you guys can swing it, great. If both people decide they feel better and can ultimately be more fulfilled people, they ultimately end up being better parents too. If they feel that they need to have some job or activity outside of the home to do that, then find ways to make it work.
Work-Life Integration
That goes to another area. You’ve got the work life and the kid’s life. I heard you mentioned work-life balance and sustainable systems. I don’t know if you use that word. Pulling all three of those levers is hard, the kids, work, and some downtime. What are your thoughts on how you manage that work-life balance or work-life integration effectively?
I’m probably one of the worst people as an example to ask that.
Me too.
It’s fair in a practical sense. I am a person who thrives on going and going. That downtime is my hardest struggle. Whereas a lot of people, when they talk about work-life balance, they’re looking for more of that downtime and balance of go and stop. I am a person who will keep going forever. I need to remind myself at times to take that downtime. You have to figure out what chapter you’re in and what’s most important to you. Everybody has the same amount of time in the day. What are the priorities? You have to have sustainable systems in place that make sure you’re meeting those priorities.
You have to figure out what chapter you are in and what are the most important things to you. Everybody has the same amount of time each day, and you have to determine your priorities. Share on XOne thing I love to do is at the beginning of every month, I sit down, pull out a notebook, and write down my top 5 or top 10 goals for this month. What does that look like on a day-by-day basis? Not only will I do that but I make myself go back to the month before, have an honest conversation with myself, and write it down. It hurts a lot worse when you don’t meet those goals and you have to write them down like, “Here’s where I messed up this month.” You carry that goal over to the next month. “What am I going to do differently this month to make sure that if I fail on a personal level, I still have systems in place that are going to carry me through to make sure that this goal is attained?”
What’s the time you were most annoyed at yourself because you didn’t progress on a goal?
I can use an example where I launched a firm. A couple of weeks into launching it, I fell ill. I tested negative for strep, flu, and COVID but I had over 100% fever for 2 weeks straight. It was just me at that point so I’m running everything. Making it through the day is getting the bare minimum done every day. You have to because you’re running this company. I’ve had certain goals for every day and every week set up but for those two weeks, I certainly was not meeting them.
I made myself sicker and made it last longer by a few days. I was trying to get up and going, sticking to my original plan again when I wasn’t well enough too. That becomes the challenge when you have my mentality or people like me. You can’t stand not meeting those goals or exceeding them. Goals aren’t set as a maybe thing that you do. Once you decide that’s what you’re going to do, you figure out how to do it. It’s not about whether you’re going to set a goal and make it or not. Once you set a goal, you are going to make it. You just have to figure out how to get there.
Personal Brand
You have to change the plan. That’s an interesting point that you talked about. Your natural state is to be busy and working. Weave that into your personal brand. Tell me about it. How did you come to the process of communicating it? I’ve seen that on the X platform and your personal brand rings through. I’d love to hear how you do that. People could take 1 lesson or 5 from you on personal branding.
Thank you. It’s funny you say that because I’m working on my next literary adventure that is more geared towards personal branding. I don’t know if you knew that or if that was more serendipitous. I’ve only shared that on one other podcast. I was thinking, “You’re ahead of it if you’ve been listening all along.” It’s funny. A lot of people have asked me about personal brands, especially when it comes to social media and things.
I got asked to speak at a conference early next year about personal branding. I started looking into it. I never considered the concept of a personal brand. One of the things that I find ironic is that since I’ve started learning more about it and talking to more people about it, one of the biggest things that people talk about in relation to personal brand is authenticity. That’s why social media has worked for me. Twitter in specific has been such a huge driver of my success, both personally and professionally.
Out of the first 10 clients that we signed with my new firm, I would say 5 or 6 were either directly or indirectly related to Twitter in some way. It’s insane. These are people who are paying a decent amount of money on an annual basis. It’s not like I’m selling a $10 product and can do it through social media. I was shocked that so much traction has picked up as a result of Twitter. You never know what person it’s going to be.
You might have 10,000 followers but it’s that 1 person lurking in the background who reaches out one day and asks you to hop on a Zoom with them and they end up being someone who owns a $1 billion portfolio who needs your help. You never know what you’re going to find there. Back to personal brand, one thing I found interesting was schools that are teaching social media strategy and how to be successful in that realm talk about personal brand. They’re teaching people how to feign authenticity, which is so ironic. How to convince your audience that you’re being authentic when you’re not?
It is so backward.
How do you teach that and feel good about it? It is what I want to know. Whatever success I’ve had online was genuinely authentic. It was me being online, being an idiot, not knowing what I was doing, and sharing a lot of information about insurance, risk management, and things that I do know. I thought at first, honestly, that nobody’s going to want to talk about this. Insurance is boring to me after almost two decades of it. I don’t imagine anybody’s going to be excited by it.
As time went on, I opened up more and shared a more genuine personality too. I started the opposite way and I was scared to be myself. Who knows if that’s going to work well or not, which is something that people struggle with, especially women in the workplace. “How much of my actual personality do I let show through? How much do I need to get buttoned up, put on the suit, and be this role?”
As I progress further in my career, I get more comfortable being myself. For whatever reason, it seems to have resonated with people. I’m leaning into it at this point. You lose some people along the way too but the way that that works for social media is also a way that it works in real life, building a better version of yourself. You have to get comfortable with the idea that as you attract the right people, you’re going to more vehemently repulse the wrong people. You can’t make everyone happy. You’re not pizza. Some people don’t even like pizza.
Be comfortable with the idea that as you attract the right people, you will vehemently repulse the wrong people. Share on XBalancing Humor And Insurance
I spent time at Amazon. They’re like, “It takes two pizzas to be able to feed the team.” You may be able to get 6 or 7 people to agree on 2 sets of pizza toppings. You’re never going to get them to agree on two identical pizzas. I’m looking at your ex-profile. You’ve got mid-funny TM. You’re just funny, not mid-funny. How do you cultivate the balance between humor and insurance? What is the right ratio? I make memes. I’ve had people scream at me to only share private equity content or operated content but I don’t care enough to be dogmatic. What do you think about that?
I thought about it a few different ways. At the end of the day, my social media strategy is still thrown at the wall to see what sticks. I don’t want to fix that so to speak because that’s the only reason it works. What I’ve been told is to try to provide 70% value and 30% viral. What that means is about 70% of the time, share information where you’re educating for free and that’s what brings people in, and then 30% of the time, lean into more viral content so that you’re expanding your reach.
Especially on platforms like Twitter and LinkedIn, I’ve noticed this works. I haven’t quite figured out Instagram yet. I don’t know if I will or if that’s my platform. What you do is that 30% viral, you’re sharing general information, something about yourself, or something you found funny, maybe some memes. I try to mix insurance with memes, which what ends up happening is it’s so niche. Only insurance people are laughing at it or people who have gone through painful renewal. Everybody else is like, “What is this? It’s not funny.”
I don’t pre-plan my content anymore. I’ll have drafts ready to go where I could probably produce content for 1 week or 2 at any given time. Most of what I share I would say 80% to 90% is off the cuff. It’s either I’m on a walk or sitting at a red light or I had this random thought. That’s what works. I try to be mindful throughout my day about what’s going on and what seems boring to me as a person who’s been doing insurance for decades.
I assume that everyone knows it but people don’t know and they appreciate you sharing with them. I’ll try to keep running notes in my phone of, “Here’s what we went through, reviewing a lease or writing a policy. Here’s this exclusion that I found.” The boring day-to-day stuff ended up being interesting and sometimes useful for people who are procuring insurance and don’t know what’s going on on the back end or don’t know what to look for.
Insurance is always an afterthought for me. I’ve been burned so many times on different things that weren’t covered. I’ve had people reach out to me continually and say, “We can automate your content generation.” Ninety-five percent of my content is me hand-typing it and then part of it gets set to graphics. Your page feels authentic to me. Do you automate it into your content? It doesn’t seem that way.
No. I don’t think it would work and I don’t think I would have found the relative success that I found on social media if I did. People can still tell a lot of times when content is automated. I saw one that was snafu and terrible. It was on Twitter and there was a social media branding company that was running several insurance pages for different brokers. They had done something wrong one day where they accidentally released the same post for 6 or 7 different brokers on the same day at the same time.
People don’t connect with brands. They connect with people for the most part. Who’s following XYZ insurance on Twitter? Probably not that many people. You have something like that happen where it’s not even XYZ insurance who’s running this page. It’s their marketing team that’s external that’s also managing these other six insurance brokerages’ pages.
I feel like that’s going to turn people off so much from everything about your brand. It’s not even worth risking something like that happening. I would rather sometimes lean into maybe I’m a little too funny. I push some people away that way for having my authentic personality versus I’ve become this robot. Nobody can relate to you anymore.
This friend of mine went to fashion and suit technology. I didn’t get it. She was like, “People want to be a part of brands but they want to connect to people.” It didn’t make sense to me until I got a Christmas card from the guy on 5th Avenue at the Ferragamo store that sold me some shoes. It didn’t hit a handwritten card. I didn’t connect those two disparate points.
One more thing on that. That’s a huge miss for a lot of companies. They’re controlling their people so strictly and how they show up on social media. Corporations and brands are able to lean into social media strategy more and let people create their personal brands. It’s within some limitations but a lot of people that I know, their companies will tell them, “You can’t go on a podcast. You can’t do this or that. You can’t even make a post without it being reviewed first by legal, HR, or whoever,” even the marketing team. The person can’t have a personal brand. It’s your company brand.
A huge miss for many companies now is controlling their people so strictly with how they show up on social media. Share on XUltimately, the ideal balance there is what sports teams do with their players, where you might know who the Dallas Cowboys are but you also know who DeMarcus is. Maybe he’s doing his charity stuff on the side. He has a family. He has this or that. Sometimes for better or worse. Some players get worse personal brands. They have different arrests or this and that but they still do a great job of maintaining two separate identities for the team and the brand. I would love to see more companies lean in that direction because you’re going to be able to increase your revenue by allowing your people to connect with other people. The best way to do that in large numbers is via social media. There’s no way to deny that at this point.
These are the over-processes or over-proceduralization. I’m Mr. Structure or Mr. Procedure. The best story I saw was General Motors. They had to come out with a dress code policy. One of the guys who used to work for me told me this. Their dress policy was two words, Dress Appropriately. That should be a social media policy but we get the lawyers involved. Unfortunately, I have friends who are lawyers. They go, “You don’t want to do these 27 things,” and then nobody does anything. It should be obvious. Post appropriately could contain it where you’re not doing any hate groups or extremist groups. That would be very obvious. You get this thing where people are paralyzed by too much governance.
That’s right. It’s a slippery slope too. At first, I was posting about all insurance and that had no traction. You lean more and more into who they are. I push some people away but depending on what your personality type is and what you might want to post about on your free time, it might push even more people away. There is an interesting graph though. I thought about it a lot before I left my career in Corporate America. It probably resonates with a lot of people where the X-axis and the Y-axis are your personal brand versus your company’s patience level with you. As your personal brand grows, the patient’s level with you goes down. You also find more success. There’s a mid-point in the middle where it says, “You’ll probably either quit or get fired here.”
Memorable Mentor
I have to see this because my personal brand has helped me and hurt me at times. That’s super interesting. I’m going to pivot hard because I want to get this in. You’ve made some content in your book. Talk to me about your mentor. Who was the most important mentor in your life? That can be a nascent one or one that’s active but that was the most impactful on you and help you be your best self.
When I was first starting my career, there was a lady named Joan. I’ve shared about her a little bit on Twitter and talked about her in a couple of other podcasts. She stands out. We talked earlier about Christina, the book, and how that company had to take a chance on her. When I started my career in insurance, I was almost nineteen years old. I was putting myself through college and had no experience. I was working at Nordstrom at the time.
I remember showing up for my interview and Joan was like, “What do you know about insurance?” I said, “I don’t know anything about insurance other than I pay for my car insurance but I learn fast and work hard. I’ll learn about insurance.” She goes, “Can you use Excel?” Joan was an older lady. She goes, “What do you know about Excel?” I said, “I can use Excel. I’m not the best at it but I’m proficient at it. I can help teach you something but anything I don’t know, I will learn. I learn fast and work hard.”
That was what I kept saying in my interview. Joan must have seen something in me where that worked for her. She ended up hiring me. My aunt works in premium financing so she knows a lot of people in insurance. I had met other people in insurance. Everyone told me, “You do not want to work for Joan. Joan is a hard ass.” Think of that movie Devil Wears Prada. It’s Anna Wintour and how notoriously difficult she is to work with.
That was Joan in the insurance world. Everyone said, “She’s such a hard ass. You’re going to have a terrible time. You don’t want to work for her.” It ended up being the greatest blessing because that tough love is an environment that I thrive in personally and a lot of people do, too. It’s a shame that we have to be so soft oftentimes in the workplace on people.
Joan threw me into the deep end of the pool. She saw that I was capable and she wasn’t going to handhold me too much. She would tell me how to do something once. If I didn’t figure it out from then on, we’re going to have a problem but you could never come and ask her the same question twice. It ended up being the hugest blessing. I probably learned more in those first 5 or 6 years working under Joan than a lot of people learned in 15 or 20 years working in the industry without someone like Joan.
We have a preference for veterans and our COO calls them high-potential amateurs. I love that so much. Accept that somebody’s going to run through a brick wall and learn fast. There’s very few things that you can’t learn in five years like some esoteric chemical engineering guy who does catalysts but it’s 97% of the stuff.
Highly capable people are the number one thing for entrepreneurship too. “How figureoutable are things to you? Are you a problem solver? Yes or no?” There are some very niche things where you need specific knowledge but outside of that, 99% of the time, it’s more a question of, “Are you going to solve the problem,” versus, “What is the problem going to be?” You don’t even know what the problem is going to be most of the time. My problem on Monday is going to be different than my problem on Friday. My problem this week is going to be different than your problem next week.
If you have the type of mentality where you’re constantly jumping over those hurdles and you know you can solve any problem, you’re going to get there. We may get there a different way. Hopefully, we both get there in an effective and efficient way but if you’re going to solve the problem, you’re going to solve it as opposed to certain people. I don’t know what the alternative is but there is an alternative. You don’t get the thing done and that doesn’t work.
Biggest Challenge And Biggest Advice
What is the most annoying or biggest problem that has hit your plate since removing your corporate shackles?
Knock on wood and everything around, we haven’t had any major systemic issues yet. For me, the biggest challenge was those operational pieces and getting all the systems in place. That’s something that as a corporate employee, you tend to lean on heavily. We have an invoice. We were lucky that we ended up signing a few clients before we even officially launch. I was, “That’s great but I don’t have a Docusign account. Let’s go sign up for DocuSign, get that contract out, and get it signed.”
We need to be able to send out an invoice. We don’t have a person who invoices things. Who’s going to do that? What system are we going to use to do it? Those first couple of weeks were a lot of learning how to swim with no floaties. Not necessarily challenging things but the things that you take for granted when you have a corporate employer who is managing those things for you.
What is the biggest piece of advice you would give to women who are thinking about becoming an entrepreneur?
There are two things that have been important for me. One is what we talked about. Know that every problem is solvable and you can solve every problem. That is a mindset shift for a lot of people. I was lucky that that is my innate personality, maybe because of the way I grew up. We’re not going to get into all my childhood trauma but I had to learn how to take care of myself relatively early on, which for better or worse has made me extremely independent and has shown me that no matter what it is, you can figure it out. Getting over that mindset shift is not a specific skillset. Knowing that you can is super important.
Every problem is solvable, and you can solve every problem. Share on XThe other thing that is not a natural skill for me at all that I had to work on and I’m still working on on a regular basis is learning how to ask for help. Yes, you may be on your own. You are your own boss but there are people who are 2, 3, or 5 steps ahead of you who are also going to be willing to help, whether it’s an official coach, mentor, or friend that you can reach out to and ask questions. A lot of times, those two traits run converse with each other.
I’m hyper-independent. I can get everything done. I can do XYZ. It becomes very difficult to learn how to ask for help but it’s so critical because no matter how fantastic and capable you are, even if you can do everything on your own, sometimes you can do it ten times faster and more efficiently with a team around you. That was a huge thing for me and a huge benefit to Twitter. I have to give a shout-out there because I was in the process of getting over that bravery hurdle to start my business.
I’ll be completely honest. I have a huge bias for action. I reached out to you at some point and also several people from Twitter and several friends in real life. I was like, “I think it’s time. It’s something that I’ve thought about in the back of my mind forever. I wanted to work for myself but never had a plan.” From the day I said it was time to the day I quit my job was two weeks or less. I knew that if I sat on it for six months, I wouldn’t do it.
I need a piece of mentorship. I have a friend that I’ve worked with. We were peers. She is highly competent. I haven’t done a good job influencing but what I always hear from her is, “I need more experience doing this. I need another year to bake.” She’ll then do something amazing. The thing was she’s like, “I should go buy my own company.” I’m like, “Yes, you should do that now. There’s no reason you should wait.” She will smash it. I have not done a good job of communicating with her because, for me, it’s very obvious looking her. What is the better way to approach her and get her to see her capability level so she will take the leap?
It’s tough to say without knowing her specifically because everybody’s a little bit different but there are common things that I see. One is self-doubt. One of the hardest things to explain to people, and we all struggle with it to some degree, is the only way to build that confidence in doing a thing is to do the thing. Maybe it’s not the only way. It’s certainly the best way. You can read so many books.
I’m a huge proponent of reading and learning but until you’re willing to take the step and do the thing, you’re not going to know what it’s like to do the thing. That’s how you build that resiliency and confidence in your abilities. You see that you can do it and you will figure it out. That goes back to the whole problem-solving thing.
There’s another thing that someone said to me. In hindsight, there are a few things where it’s like, “This is what sent me over the edge and finally made me take that leap.” One of the things that someone said to me was, “Sit down and think about your life five years from now. If you made this leap, what’s the best and worst situation that you could have? If you don’t make this leap, what’s the best, worst, and most likely?” It’s three situations on each side. “If you decide to do this for yourself, what’s the best, worst, and most likely? If you don’t do it, what’s the best, worst, and most likely?”
I sat down and looked at that. They were like, “If you take this leap, you go on your own as an entrepreneur and your business fails miserably. Let’s say that you make no money and you lose everything you’ve invested in,” which, for me, startup costs were minimal. This was a low-risk venture for me but it’s different for other people. Worst case, they were like, “You’re not going to be homeless because you have skills in a network. In 1 year or 2 years from now, if ATW has failed miserably, what does your life look like?”
For me, it was obvious. I go back to being an insurance broker. Maybe I’m not happy. Maybe I’m working for a big corporate boss again but I’m able to maintain my lifestyle and feed my family. Everything’s going to be fine but I’m going to be innately unfulfilled and feeling all the same things I felt before I made this decision, which I know I’m capable of more. Deep down, when you’re most scared of doing something, you also know that you’re capable of that thing because if you weren’t, it wouldn’t even be in your brain or heart that you should pursue that thing.
I’m not just saying, “I woke up one morning and thought I wanted to go start a coffee shop.” If you’ve been thinking for a year about starting a coffee shop and you don’t know if you have all the skills yet, do your research and due diligence, especially with something completely different from what you’ve done in the past. That’s there for a reason. Not everybody’s thinking about doing that. If that’s weighing on you, take the steps that you need to take to see that through.
Some people are afraid they’re going to have to go back to Corporate America and they’re going to feel silly. I was looking at going to another private equity firm. I believe I would feel sillier at 70 if I didn’t take my swing. That scares me way worse.
You hear that from so many people. It sucks if you have to tuck your tail between your legs and admit that you failed but in general in life, not just for business, one thing that everyone can do to make themselves happier immediately is stop caring so much about what other people think. That’s a perfect example of that. I did that with the book, too.
Everyone can make themselves happier immediately by stopping to care so much about what other people think. Share on XIt wasn’t perfect when I released it. I wasn’t totally happy with it but I finally got to a point where I said, “I’m not taking any criticism from someone who hasn’t released and published their book. If they have, I’ll take their criticism happily because there are things that I can learn, improve, and grow.” I hate to use the term because it’s so overplayed but if I’m in the arena doing this thing, you don’t get to from the cheap sheet sets to tell me that I suck at it or at least that’s going to roll off my back.
With the people in Corporate America who are very successful, I know a lot of them who have this itch to do their thing one day but they’re scared. Even if you went out on your own and ultimately, it was a failure and you had to go back for a few years, figure out your next step, or even if you went back forever. There are a lot of people who would appreciate that. Not only appreciate it but envy it in a way because you were able to do the thing that they may never do.
I can pinpoint the exact moment that I stopped caring for what other people think. I was 34. There was a senior partner at McKinsey who told me to do something this exact way and this is what he wanted done. There was a senior partner McKinsey who told me he wanted it this exact way and how he wanted it done. They were both diametrically opposed to each other. I physically couldn’t make both of them happy. I was like, “I’ll take your input and his input. I’m going to do what I think.”
Book Recommendation
That was a six-week process of going back and forth and trying to broker a trade deal that went horribly awry. It was never going to get anywhere. Finally, I said, “I don’t care where this is going to go.” Here’s the last question I ask everybody. Other than your book, what is the most impactful book in your life that you recommend everybody read?
For people of faith, I’m going to say the Bible. I’m going to throw that one out. It’s a little cheesy but it’s something I read every morning. It’s important to me. Outside of that, I didn’t come prepared for this one. I should have.
My gut says you’ve read too many and you’re worried about picking the right one. It can be off the top of your head.
I’ll send you a picture of my bookshelf. One of the most recent books that I read or did on audiobook was a David Goggins book. A lot of things like that are helpful for mindset. Also, Jocko Willink. People always think it’s funny coming from me because they think men read these things and women don’t. They’re great for everyone across the board. It’s a weird marketing thing that they’re more geared towards men. Those are great. Zachary Levi wrote a book. I’m blanking on the title. It’s something love but that was a great book about overcoming your traumas and meeting yourself at the best version of yourself. I read a ton of books but those are some of my favorites.
I’m looking up Zachary Levi’s book. Is it Go Love Yourself or Radical Love?
It’s Radical Love. That was a super easy read. You can get through it in 1 day or 2 but had some good points. It was beneficial from a social and emotional maturity standpoint to read through.
Episode Wrap-up
It has been great getting to know you better. Where can everyone get in touch with you? They can find your book on Amazon, SO SHE DID. Where do we get in touch with you?
On LinkedIn, it’s @SkylarRomines. On Twitter, it’s @SkylarRomines. If you use Instagram, I don’t use it much but it’s under my name, @SkylarRomines. I’m pretty much everywhere with the same handle and name.
It’s super good to get to know you. Please, read the book. It was an enjoyable read. It took me about three hours and I was making notes. It’s super good to get to talk to you again.
Talk to you later.
Bye.
Important Links
- SO SHE DID
- ATW Advisors
- CREW Orange County
- Go Love Yourself
- Radical Love
- @SkylarRomines – LinkedIn
- @SkylarRomines – Twitter
- @SkylarRomines – Instagram