Ep. 135/ A Pivot After a Layoff in her 50’s: Headshot Photographer Alissa Randall’s Inspiring Journey


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Alissa Randall is a dynamic headshot photographer who shifted from the corporate world to running her own business in her 50s. She shares how she turned a significant career setback “I was sad for 10 minutes” into a triumphant pivot by launching All About Headshots and later expanding with her heartwarming PupShots. She says a layoff “pushed me to chase my passion for photography,” and she shares tips on having a great photo shoot, the confidence-boosting power of tailored clothing and personal color preferences, and her expert tips to help clients relax and enjoy their sessions.

We both share our personal journeys of leaving corporate jobs to seize control of our professional lives, highlighting the financial and emotional rewards that come with entrepreneurship. Alissa offers valuable insights into overcoming imposter syndrome, the significance of a professional online presence, and the crucial role of supportive communities and networking in achieving personal and professional growth. I am absolutely inspired by  Alissa’s incredible story and gained even more tools to add to my own entrepreneurial toolkit.

In this episode you will learn:

  • After getting laid off, Alissa says how she was sad for “10 minutes” - 3:45

  • How having photographers in her family and her dad was an entrepreneur impacted her career - 12:36

  • Advice on how to take a great photo - how to be comfortable in front of the camera - 20:26

  • How to turn obstacles into opportunities - 30:22


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In this episode you will learn:

  • After getting laid off, Alissa says how she was sad for “10 minutes” - 3:45

  • How having photographers in her family and her dad was an entrepreneur impacted her career - 12:36

  • Advice on how to take a great photo - how to be comfortable in front of the camera - 20:26

  • How to turn obstacles into opportunities - 30:22

Quotes from our guest: 

  • "Am I working harder than I was at the nonprofit? Of course. But I'm working for me and I'm working for my clients. And there's really something magical about that because I'm forming it." - 10:15

  • "Before I even took one photo as a photographer with all About Headshots, I had once  introduced myself to somebody as a professional photographer. My husband was with me, and he said, you haven't even taken one photo yet, but you're introducing yourself as a professional photographer. And now I'm a professional photographer. And it's amazing, and I love it. And I feel so grateful." - 16:37

  • "Tailored clothing and knowing your personal color preferences can make a big difference in how you feel during a photo shoot. I always encourage my clients to bring multiple pairs of glasses for flexibility, and remember—any glare can be retouched. My goal is to make every session as comfortable and enjoyable as possible, almost like a spa day with music and professional makeup." - 25:34

  • "I truly believe that obstacles are opportunities. Losing my job as a Chief Marketing Officer was a turning point in my life. It pushed me to chase my passion for photography, and now I can't imagine doing anything else. It's never too late to pivot and find joy in a new career." - 33:59

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LINKS:

Alissa’s Website


Kim (00:02):

Meet Alissa Randall after getting laid off as a chief marketing officer. She says she was sad for about 10 minutes and then launched into her second career in her fifties and is now a highly sought after headshot photographer Alissa talks about turning obstacles into opportunities and how growing up with photographers in her family impacted her. And she gives incredible advice on how to take a great photo and how to be comfortable in front of the camera. Lastly, her positivity is just infectious. Welcome to the Exit interview with Kim Rittberg. Do you work for yourself and want to supercharge your business while still having fun? Well, this is your go-to podcast, part MBA Part Cheer Squad. Every week I'll be joined by top business owners who share the secrets to their success. After I found myself working during childbirth true story, I quit my executive media job to bet on myself fighting the fear and imposter syndrome to eventually earn six awards, an in-demand speaking career and features in Fast Company and Business Insider. Now I'm here to celebrate all you rock stars betting on yourself, and I want to help you win. Tune in every Wednesday to hear from remarkable founders and don't miss our Solo Friday episodes, a treasure trove of video and podcasting mini masterclasses with me. Exit the Grind, enter success on your own terms. Don't forget to subscribe today and grab my free video tips at my website, kimrittberg.com.

(01:31):

Before I tell you about our awesome guest, I just wanted to let you know we have some incredible webinars coming up. I only run them a couple times a year, so do not miss it. And you can sign up online. I'll put the link in show notes. This is Five Insider Secrets to Getting Clients From Social media and video. It's an interactive webinar, it's a marketing workshop. If you're a real estate agent, a business owner or a coach is perfect for you. You are going to learn the number one thing to do to get clients from video and social media, what most people are doing wrong with social media content that's wasting their time. The top trick you can use to make video that attracts leads and clients, how to show up confidently on camera and how to engage leads on social media. So there are workshops coming up on January 15th.

(02:09):

Make sure to sign up and that's at kimberg.com/webinar. Alissa Randall is a headshot photographer who transforms lives through the power of visual storytelling. As the founder of All About headshots by Alissa Randall, she specializes in helping individuals and professionals present their best selves to the world with both authentic and empowering headshots and branding photos. Alissa's journey to becoming a sought after photographer is as inspiring as her work in her fifties. After decades of working in business development, marketing, and most recently as a CMO for a large educational nonprofit, she made the bold decision to pivot her career toward her passion for photography, fueled by empathy and a desire to make it tangible impact on people's lives. Alissa built her business from the ground up, combining her seasoned professionalism with her creative vision. In 2024, Alissa expanded that creative vision by launching all about pup shots, a heartfelt venture dedicated to capturing the unique bond between people and their beloved pups, a connection like none other. Alissa, I am so excited to have you here. I know you have a really crazy pivot story. I love a good pivot. First, tell me right off the back, tell me about your exit.

Alissa (03:15):

Alright, yes. So Kim, thanks for this. This is amazing. So alright, my exit. So during a one-on-one meeting with my then boss, because as a chief marketing officer you have one-on-one meetings with your bosses. And so during my one-on-one meeting with my boss, when I logged in, I saw HR and my boss was on for about 30 seconds and she said, well, we no longer need the CMO position. And she got off the phone and then I was left with the director of HR and he started talking and he was lovely and he started talking and I said, Kevin, I cannot hear you. Let's reconnect Monday. So I sat in my office at home for about 10 minutes and said, huh, okay, I've lost my job. Now what am I going to do? Alright, I'm going to start my business. So I called BNH because I had these lights. I was a natural light street photographer. I've been doing photography my entire life as a fun side hustle. It was a fun side hustle for you. Not even a side hustle. It was a non hussle. It was, Hey, let's go and just do street photography for fun

Kim (04:18):

Of people or of buildings

Alissa (04:20):

Of people of people,

Kim (04:21):

People

Alissa (04:21):

Always of people. And prior to all of this, my brother had said to me, you should be a headshot photographer. So I had trained with a premier headshot photographer, so I knew how, but I was sitting here and thought, huh, okay, I'm going to start my business. And I called BNH, who put me in touch with the rep for the lights that I bought, and I said to him, well, my position was eliminated today I am starting my business. Can you come over and teach me how to use these lights? And he said, yes. And so that Saturday we were both standing in my living room with the lights and he was teaching me how to use them.

Kim (04:55):

Okay, BNHI love by the way, for anyone who's not based in New York, it's like this mega, mega, it's almost like a warehouse size tech camera videography. So they came over and they helped you set up all this stuff and you're like, this is day one of my business.

Alissa (05:08):

So Cliff came over, he was the rep at the time for ProPhoto, and he was in my living room teaching me how to use these lights. I am eternally grateful to him. So yeah,

Kim (05:19):

I want to go back for a second. So when the HR person said, when you said, I can't hear you, could you really not hear him? Or you needed time to process?

Alissa (05:26):

I needed time to process. I had been there for 13 years. I started the department in December of 2009. So I thought that I would be at that nonprofit until I retired. I really thought, but it was a, oh boy. But it was the greatest gift that I could have ever received. Why is that? Because I would've been there until I died, basically. And it forced me to pivot. It forced me to start my own business, and I am so thankful. I am just so thankful that I was able to start all about headshots.

Kim (05:59):

Because you feel like this is what you're meant to be doing?

Alissa (06:02):

Yeah, this is what I'm meant to be doing. Yeah. I am told by people that I'm living my life's purpose, which is helping people see themselves for the first time and helping them find their power through photography. And it would've not happened had I still been there.

Kim (06:17):

And then sometimes when people say, oh, what could be not the word catastrophe or disaster or tragedy, whatever, can just turn into triumph really quickly once you shift. How long were you in the stage of shock and upset that they laid you off until you were like, no, no, this was awesome. Was it a week or was it two years?

Alissa (06:35):

It was 10 minutes. So after I called BNH and I spoke with Cliff and he had come over, he was coming over that weekend, I called a colleague of mine, a person that I knew who was a recruiter for businesses, and I said, well, I'm going to start this business. Let's touch base in three months. And so she called me in September and I said, no, I'm still doing this. Let's touch base in December and called me in December and I said, I'm never going back to corporate. This is it. This is it. It's amazing. I feel like I'm not working a day in my life because I get to work with such fabulous people and really, really help my clients capture who they are. And it's amazing. So for anybody who's afraid of taking that leap, I would say just go for it. Because you never know what adventure might be before you that you just wouldn't even know because you're holding on because of fear. And it was the greatest gift. And when I tell you 10 minutes, I really mean 10 minutes. I sat here for 10 minutes and that was it.

Kim (07:44):

I love the idea of fear. I'm actually giving a keynote on fear later this year because I think for me, first of all, I have to say I love the stories of people when they're laid off. I've been laid off. And they were like, I took it really well. And they were like, thank you for taking it so well. And in my mind, I'm like, you got on a mystery trip to New York without telling anyone. Obviously I know what's happening. You know what I mean? I know you're coming here to lay me off. I'm not happy here. Things are getting restructured. How stupid do you think I am? And then there was another place I worked at, they made me sit there while they laid someone else off. I had to be there in the room with them. And I'm like, I'm not laying this person off. You're laying this person off, and I know this whole unit's going to close within six weeks. What are you doing? And it was just so inhumane. It was just so not nice. And then this person didn't necessarily get any comfort out of me sitting there.

Alissa (08:33):

They were probably more embarrassed that you were sitting there.

Kim (08:36):

And I was just like, oh my God, this is horrible. But I think also those situations are either red flags or just indications of this industry doesn't serve you anymore, or I felt like it wasn't stable. I'm like, oh, you could work your butt off, but it's not a stable industry, so what's the point? Might as well do it for yourself. If you're good at what you do and you're not afraid to put yourself out there, the sky's the limit. And so I think sometimes to your point, it ends up being a blessing in disguise. I do feel like I had a couple of jobs that just were like, the job you take and the job, it ended up being not a match, just not the same, really not a great match and not a good experience. And I was like, this is the universe telling me I don't want another full-time job. But also the universe is telling me your industry is changing so much. That full-time job is not going to be what you want it to be. It's not going to necessarily be there in two years or five years. So okay, self-employment is a risk. Well, so is my industry.

Alissa (09:26):

Right? Exactly. Yeah. Being employed. And that's something that's a really good point, Kim, because people say, oh, I don't want to go start my own thing because it's not secure. Working for somebody else isn't any more secure.

Kim (09:39):

And it depends on what industry you're in. I agree with you. Some industries, you'll always have a job and whatever, but a lot of industries are contracting. The digital revolution has changed so many industries. And to pretend that you're going to be there, get your 30 year paperweight, it's just not true.

Alissa (09:56):

But when you work for somebody else, you're at their mercy, right? I mean, so they are in charge of your longevity on some level, yes, of course you have to do a great job, but that other person is deciding whether or not you have a job. As an entrepreneur, it's lovely because, yeah, am I working harder than I was at the nonprofit? Of course. But I'm working for me and I'm working for my clients. And there's really something magical about that because I'm forming it. I'm making up the rules as I go, saying, what's working? What's not working? Does something need to shift? And it's fantastic.

Kim (10:32):

Okay. So if you were a CMO at a nonprofit, you said you had sort of worked under a headshot photographer. Is that kind of on the sides of your business or was that years before? Talk to me about how you got interested in photography. How did you have the photography spark and how did you nurture it such that when you were laid off, you're like, I'm ready to start this business?

Alissa (10:53):

So when I was a little girl, my mom was taking a photography class and she was actually taking the class across the street from where I currently live. I live in Verona, New Jersey, and there's a park, Verona Park. And I would go with her to help her do her homework, or I would watch her do her homework. And I thought, this is fantastic. And that's really what sparked my love of photography. And then my brother David is also a photographer, and he lives in Hawaii. And Dave was in town now, or going back, I guess November of 2022. No, no, November of 2021 for Thanksgiving. He was home and we were shooting in the park, just playing. I wanted to go get his camera. I loved his camera. So we went to New York, we went to BNH. And on the way out, David said to me, you should be a headshot photographer. And I said, what? I had never heard of it. What age is this? What age is this? This is right before I started all about headshot. I was like, oh, when you were 15 now. Got it. So I had never heard of headshot photography ever. And I trained under the premier headshot photographer. He said, you're great at it. And then when I lost my job, when my job was eliminated, I said, I loved it. Let's do it now.

Kim (12:04):

And that was it. At a company, you never had someone come on and do headshots. You never went to a headshot photographer. That wasn't a thing that you had seen that you were like, I want to do that part, that thing. I mean, as a

Alissa (12:13):

CMO, of course I've had headshot done before or at conferences or I've gotten them myself. But no, it was never, I want to do that until I trained. And then I fell in love with it because I love photography and I love connecting with people, and it made perfect sense, and it's my passion marrying, helping people, getting to know people, and photography. It's a perfect combination.

Kim (12:36):

It's so funny because when I interview people on this, I like hearing people's backstories for you that you actually are from kind of a family of photographers or they had a love of photography. And when I was a kid, my mom was a photojournalist. She's like a Jane of all trades. So she was a journalist, a writer, and a photojournalist. Then she went back to get her law degree, and now she's retired, does art and poetry, and I love that. But I feel like that creative spark was there. And then my grandpa had a lace store. So one of my earliest memories is touching the lace and picking out patches and sewing them on my bags and making things. Literally, I was seven years old and I was making a wallet, and then I started making jewelry, and then I had a jewelry business. And I do think those early years are so formative, and it makes such an imprint. Well, first of all, I better watch out what I expose my kids to. I'm like, I'm like, don't go into media. Just kidding, just kidding. I do think those formative moments in your career. And my dad was an entrepreneur though, so I definitely was not interested in being an entrepreneur because I saw him work really, really hard. So I was like, oh, I mean, I'm hardworking, but he looks really tired. I hadn't thought

Alissa (13:43):

About that. My dad was a lawyer and he was an entrepreneur. Oh, he ran his own law firm.

Kim (13:49):

That

Alissa (13:49):

Didn't hit me until just now,

Kim (13:51):

Until

Alissa (13:51):

You said

Kim (13:53):

That. I honestly had that epiphany also from a guest. They were saying about their own parents. And I said, oh yeah, my mom's really already, but also has a law degree. My dad ran his own business, was a engineer, computer engineer, and I was like, oh, okay. And now all three of my brothers and I, my two brothers and I, we all work for ourself, which is crazy. Okay, so you launch your business. How did you find clients?

Alissa (14:15):

So lots of word of mouth. So in the beginning, I was photographing people just to build my portfolio so I wasn't charging them. And then my first client, my first paying client, I wasn't intending on charging her for the photos. And she looked at these photos and she said, oh, I'm paying you for these photos. And that was it. And after that I started charging people, but it was really word of mouth, networking, really lots of word of mouth and networking.

Kim (14:44):

I love that. She's like, these are so good. I insist on. I've had moments like that where someone's giving me a discount or try to be nice. I'm like, this is good. Don't give me a discount. I was like, this is really good. I've had moments like that. So how many years have you been in business and what did it look like? What were the hardest parts? I know that you're running your business and you love it now, but it's not so easy at first. So talk to me about the harder points of building your business.

Alissa (15:07):

So the business started May 19th, 2022 and the hard parts. Well, it's interesting being organized. So as a CMO, I was incredibly organized and as an entrepreneur and handling quite a bit more on my own. And I say to people, I used to be so organized what happened? So that's something that I'm putting into place now. I'm trying to put in processes and spending the next few weeks going through my data and cleaning up my data and HubSpot, and then just positive mindset. So not having an imposter syndrome, can I really do this? Yeah, I can really do this. I've done this for the last number of years and it's been great. So just staying ahead of things and staying out there

Kim (15:56):

Is really important. Can I ask you, in terms of what you were earning as a CMO and the best year of your business, how do those compare financially?

Alissa (16:04):

I'm doing much better than I was as A CMO.

Kim (16:07):

I'm going to ask you that and then you're going to say it in a way that you're celebrating yourself, actually huge. So I'm going to re-ask you that now. And I'm not editing that out. I'm not editing that out. Alissa, financially compared to being a CMO of a nonprofit and now that you're running your own business in your best year so far, how does it compare financially? It's amazing. It's amazing.

Alissa (16:26):

It's truly amazing. But more importantly, you enjoy it. I love it, and I feel really grateful. So every day I am able to say, this is what I get to do for a living. It's funny, before I even took one photo as a photographer with all about headshot, I had, once I introduced myself to somebody as a professional photographer, my husband was with me and he said, you haven't even taken one photo yet, but you're introducing yourself as a professional photographer. And now I'm a professional photographer, and it's amazing and I love it, and I feel so grateful, and I feel so grateful to my clients for putting their trust in me. I like the idea of, you followed

Kim (17:06):

The rule of dress for the job you want, or the Oprah, whatever mindset thing, say what you want. But if you dress for the job you want and you say you're doing it, it'll happen. So I'm a speaker now, but I put speaker on my LinkedIn profile before I was really a speaker, but I knew it was going to happen because I knew it. I was like, I'm ready for it. I'm already doing it in small ways. But you can't step into that role until you believe you are right. Exactly. Exactly. Yeah. What's funny with the finances, I always, not that I feel weird asking it, I was a journalist, you have to ask the questions. If someone doesn't want to answer, no problem. But so many of us, we have this weird thing about sharing that this, you don't have to say your exact revenue, but this job is more lucrative than my full-time job. And people think self-employment is scary and risky, which it could be. But if you're doing what you love and if your clients are enjoying it and you're marketing yourself well, you absolutely can. And so this year I did much better than I did at my highest paid media executive job. And I don't necessarily lead with that because I really am mostly just appreciative that I have awesome clients and that I get to help them and that they're appreciative of my work.

(18:17):

I feel like mostly I'm happy that I have a good work-life balance and I love my clients and I like the work I'm doing, but also you have to say, what a great sign from the universe that you're making more money doing something you love, that you feel like you're meant to do rather than being at a company. And so I think that it's a mixture of things is a, it's capitalist great. So capitalist society good. You're earning more money, yay. But more importantly, it's an indication that you're doing what you're meant to be doing.

Alissa (18:41):

Right. And I'm grateful also because I'm able to help other people, so I'm able to share it. I am really philanthropic. I like to give back as much as I can. Yeah, so it comes full circle, I believe.

Kim (18:55):

I think you're right too though. I feel like, I know this is going to sound weird. It's not that I'm not a generous person, but I think about in media, I liked doing it because it's like fun for me. I get to tell stories and interact with people, but now I really am helping people. I'm actually helping people grow their business. I've had clients be like, I literally made tens of thousands or hundreds of thousands of dollars more because we worked together. And I'm like, I'm actually helping people. And that's such a mindset shift that that's actually a huge part of why I'm doing it now. Whereas I first was like, it's fun to story tell, it's fun to make videos. It's like, I like this. I'm good at it. Yay. I like to train people to speak in public, but now I realize I'm actually changing people's lives, their confidence, but actually their livelihood. And also to your point, I think we have a lot of similarity in that I'm changing how someone sees themself. And when you change how someone sees themself, that impacts everything in their life,

Alissa (19:47):

Their

Kim (19:47):

Personal life, their professional life, their family life. I think it took me a while to realize that because I hadn't been doing as much one-to-one with regular people. I'd mostly been doing media work. And so I think it's been a real mindset shift for me to be like, this is so cool. I'm actually helping people. This conversation with you has made me think about that, how you framed it at the beginning, where you're like, I am helping people see themselves in fresh ways, so I'm going to steal that line, Alissa,

Alissa (20:15):

Please do. And people cry in the studio all the time when they see their photos for the first time because they have forgotten that they could look like that. And it does really help them find their power.

Kim (20:26):

Talk to me about some of the other things, like what happens, someone comes in, they haven't really done a headshot, and then what's the process? How do you get someone into your studio and make them feel comfortable? I know for me, for my clients, getting on video is really hard when they haven't been doing it at all, ever, maybe. So same for you. Your clients come in, they're getting their headshot, maybe they're not comfortable. How do you loose them up? How do you get best photo out of them?

Alissa (20:48):

Usually what we do is with a longer session is we have a styling consultation. And the styling consultation is where my clients try on their clothes for me and I can help them choose which clothing they want for what use case, that sort of thing. And then they bring the clothing to the studio. So now they're prepared. I say to them, we're going to play, that is what we're going to do. So they have hair and makeup with my makeup artist who's amazing, and then they come to me. We do a test shot to make sure the makeup looks perfect, which it always does. And then we move into the session and I am trying to get them to laugh and relax and I could feel what they need, and I'm just there for them to make them comfortable. That's my job, to make them comfortable. And we just play and we have the best time in the studio and they see their photos. They usually start to cry because they see the photo for the first time, so they haven't seen themselves in a long time. And then we have a shoot where I'm connected to the monitor, so I'm calling them over doing lots and lots of facial expression coaching, and it's very, very interactive. And then at the end is when we look at the images and choose the images. But it's a really lovely experience. It's all about them.

Kim (21:58):

As they're looking at the monitor, they're not feeling self-conscious seeing themself. They're feeling good. They're feeling good. Yeah. Yeah, they're feeling good. And at what point, so they're coming in for a headshot for you, how does it help them in their career or in their life to have this incredibly professional

Alissa (22:11):

Headshot? I've heard from so many people that getting a headshot, that my headshot, the headshot that I took of them has helped them get a promotion or get a new job. I mean, it's changed their life. It's changed their life. I mean, we know that having a strong digital brand is really important, but it also gives them that confidence and they show up more confidently.

Kim (22:32):

Yeah, it's interesting. I worked in, when I worked in journalism, I would get pitched a lot of people to be on camera, to be the expert in a TV segment, a doctor, a lawyer, a psychiatrist, whatever. And what you're saying is true, and obviously it's so much more important now. When I was in tv, it was

(22:48):

Not as social media heavy. Sorry. I was in online media already when social media was heavy, but when I was in tv, social media, it wasn't as big of a thing. But already I was like, if this person doesn't have a professional presence online and they haven't invested in themself, are they really the level of professional that I can be putting them on TV as an expert? I have to put my name on the line for my boss. Everybody has a boss that they have to vouch for this person. And so to your point of having that headshot, having that professional presence online, having that logo, it's all a part of this package that says, I'm a real professional who invests in themselves. Not only am I good at what I do, but I'm aware that I need you to see that I'm a real professional.

(23:30):

And I think it is really, really important. And I know this not just from my opinion, but this is my professional opinion being a journalist for so many years. And I feel the same way, even when I get pitched people on the podcast, most people already have that really strong presence when they're pitching me for the podcast. If someone sends you a website or a headshot or a one sheet and it's casual and it's not written well, you're not going to think highly of them. You're not going to think that they're a really a strong professional candidate for a job or a promotion or being a guest on a podcast or being featured in the press or whatever it is that they want. And then, so speaking of getting comfortable, so we're in the age where everyone's either taking their own photos or maybe they're going into the studio, or maybe they're taking branding photos. What's your advice for someone to feel comfortable? I just said that so weird. As someone is either taking a selfie or going in for a branding shoot, how can someone feel comfortable when they're taking photos? The most important or the beginning

Alissa (24:20):

Step number one is to be in clothing that you feel fabulous in. If you are in something that you don't feel great in, you'll see that in camera, whether you're taking a selfie or you're going to a professional photographer, and then also try to get out of your head. So Kim, when you and I first started, I was nervous. So you had me do this breathing exercise. I do the same thing with my clients. They're standing in front of the lights. I can see them holding their breath, and I say, okay, let's pretend we're in the yoga class. Take a deep breath in, take a deep breath out, and you can see the stress or the nerves fade away. So if you're taking a selfie and you're nervous or you're working with a professional photographer, just step out of your head and breathe. Don't hold your breath because you'll come across much more stiff and you want the picture to be relatable and really capture who you are and really capture your personality. If you're in your head, that won't happen.

Kim (25:16):

Right? It's so funny what you were saying about wearing an outfit you like. It's so true. I have two dresses that I just love. I put on, I have this crazy magenta jumpsuit. I wouldn't wear it necessarily for headshot, but when I wear it, I'm like, this is fun. I feel great. Everyone's looking at me because I'm wearing a fun, bright color. And so you're right that it really does change your

Alissa (25:34):

Mindset. Yeah, absolutely. And whether we're doing headshots or lifestyle, branding, photos, fit is so important. If you're wearing something that is too large, you're going to look larger. So wear something tailored and then colors, any color, whatever makes your train go, woo is what you should be in. So fabulous clothes that you love, that you feel great in. And then just try to get out of your head.

Kim (25:58):

I feel like I always get the question about glasses. What do you recommend about glasses and glare and all that?

Alissa (26:04):

Yeah, absolutely. So if you have multiple glasses, bring them to the shoot because you could accessorize your outfit with your glasses. And in terms of glare, don't be afraid of having glare because your photo, if you're working with a photographer, will go off for retouching and the glare will be removed. If you're doing a selfie, you have to be more careful.

Kim (26:25):

Did you ever have someone who came in and they were so nervous and you had to bring out the whole enchilada, then what do you do? What does that look like?

Alissa (26:32):

Yeah, yeah. So when I open the door, sometimes people say, I'm so nervous. And I said, don't worry, we're just going to play. I put on music and they work with my artist, makeup artist, and that's really relaxing. It's like a day at the spa. She and I have talked about getting a recliner so that people can fall asleep when she's doing their makeup. And then they come to me and they're nice and relaxed, and then we just have a great time in the studio. A lot of people equate getting their photos done with going to the doctor, and I completely understand because people are nervous about that and having your photo taken, it's very vulnerable, but it's a very, very safe space. And people, they become comfortable,

Kim (27:12):

Which is all I want for them. I love that. Alissa, this is such a good conversation. I feel like it's so inspirational. I don't know that I flagged to people in the interview that your pivot happened in your fifties. I don't know that we'd mentioned that. It's in my notes, but I just wanted to say to people, you're on your second career in your fifties, you're a few years in. It's going great. I just want to say I feel like that's really inspirational. So many of us, I think we envision our careers in chapters instead of our grandparents' generation where it was one job for your life. When you think about this chapter of your life, what do you see it as? How do you see the arc of it? Where do you see all that headshots going?

Alissa (27:52):

I see doing this until I'm in my seventies. And it's funny, when I was first starting, I spoke with a coach and I said, I want to have this incredible second career where I am speaking to groups of young people, of young women talking about this career. I think, well, I know I'm in this incredible second career, and I can see doing it until I'm in my seventies.

Kim (28:16):

I love that. And does everybody come to you? Do you go to places? Is it the sort of thing sometimes people come to your studio and sometimes you go to a place and do a setup somewhere?

Alissa (28:24):

Yeah, so both. So I have my studio in New York City, but we go on road shows where we'll do headshots and lifestyle branding around the country. And then if people need me to come on site to do photos, I could do that. I do corporate photos, corporate team photos and events. And then if we have a branding shoot, let's say, and someone wants it in their office or at a workspace, we could do that too. So it's whatever the client needs. And then I've been asked by clients to do family photos. So we've started doing family photos, and then recently, because I lost my dog Chumley, he was 18, I rolled out all about pup shots to capture the connection between the pet owner, the pet parent, and their pups, because there's nothing like it. And I did not have professional photos of chumley, and I thought, I don't want anyone else to go through that. So that's why I have all about pup shots also.

Kim (29:17):

Oh, I love that people love their pets. I bet that's more lucrative than anything else. People love. They'll pay any amount of money for their pets or their kids, but not necessarily for themselves. Yeah. Alissa, is there anything I didn't ask you that you would like to share?

Alissa (29:31):

No, this has been incredible. Thank you. And I would say if you are thinking about taking the leap from corporate to starting your own thing and you're afraid, just go for it. Just go for it. Take the leap, and if you want to chat about it, I am happy to talk to you about it. So happy to brainstorm.

Kim (29:47):

Oh, yeah. I was like, oh, wait, Alissa had advice. Did I forget to give any of her advice out? What was something you wish someone told you before you started your

Alissa (29:56):

Business? Well, certainly to have the processes in place and then make sure that you ask your clients what will delight them. So as a photographer, I want to know, does the client have specific shots in mind? Have they seen something that they say, oh, I would really love that for myself. So make sure you ask your clients what would delight them. Is that how you say it? What would delight you? Yeah, what would delight you from this session? Which

Kim (30:22):

Means not what makes it acceptable, but what makes it amazing. Yeah. What makes it amazing. I know one of the things you told me before the podcast was see obstacles as opportunities. Talk to me about that. What happened in your business that you realized that, that that's something that you want to pass on?

Alissa (30:39):

Well, not so much in the business, but when I lost my job, that was a huge obstacle. But look at such a great opportunity came from it. My whole life changed because of losing that job and starting all about headshot.

Kim (30:52):

Yeah, it's funny. I think it's like it only happens when you have that big moment. I remember I always tell people it's like I was working in the hospital when I was having my second child, and I loved my career, but I was like, this is a hundred percent not what I wanted out of my career. I don't want to be in the situation where I can't have two days to myself to give birth. No hard to hard, no hard, no, I am a rom-com hero in a movie that I don't want to watch. That's not the character I want to play. And that was a real just moment of just like, that's a moment of clarity and saying, okay, so now and then I do. I feel like I've had the most incredible year. This is so fun. I get so much time with my kids. I've been traveling a lot. I feel so happy. And I literally have people who are paying me money sending me notes going, Kim, thank you so much for our work together. I'm like, you're paying me. You don't need to thank me. It's my job. But not only do I have good clients, but they appreciate the work I do, and it's like, this is the best. Amazing. It's amazing. I just feel it's amazing. Super lucky.

Alissa (31:55):

I got a call at my dad's funeral from somebody at work, and I actually said to them, you know what? I'm really sorry. I can't talk to you right now. I'm at my father's funeral, and when I first started the company, I was walking to my garage to go to a networking lunch, and I thought to myself, I don't have to tell anybody where I'm going. It's amazing. And the fact that you were in the hospital giving birth, yeah, no, that's not okay. So now that's what I say. You can make the rules up as you go along and make sure that it works for you and make sure that it works for your client. But the freedom is amazing. It's incredible. And being able to help people in ways that they need help

Kim (32:35):

Is incredible. And I think you're right. I think one of the things that I've learned just from this podcast, from life, from being a business owner, you don't have to explain to anyone what you're doing and who you're doing with and why. It's nobody's business what I'm doing on any given day. They also don't need to know that I work till 11 o'clock one night. It fixed nobody's business. It doesn't matter. I just feel like, I remember when I had a big team in media, someone emailed me, I have PMs today, or I have this, and I'm like, yeah, just take a sick day. You don't need to tell me everything. Not in a judgmental way, just not everybody needs to know everything. You can keep it to yourself. You're allowed to just say, it doesn't work for me, or I'm busy. Here's another time. How about this other time, be flexible, but you don't have to give up everything. No one's giving up everything for you. So don't give up everything for anyone else.

Alissa (33:21):

Yeah, and it's an opportunity to create magic, really, truly.

Kim (33:25):

Yeah. I ended on a negative note and you're like, oh, yeah, it's magic. I'm like, yeah, it's magic. No, but I do think that along with the flexibility is this reality of you're in control of your life and live that life how you want to live, and you don't need to give people explanations or answers. Serve your clients in the best way that you can, but also live your life according to how you want to live your life and don't feel the need to explain things. Someone said no is a full sentence. I used to be like, I'm sorry, I can't come to your party. I have to do this other thing. It's like you could just be like, oh, I'm sorry I'm busy, or I'm sorry I can't come. I would like to, but I can't. You don't need to explain why.

Alissa (33:59):

But also, you had asked me a question earlier, and I just want to touch back about it for a second. When you're building your business, and I know that you found this as well, people really connect with authenticity and they want to get to know and trust you, and that's something that's really important as well. Putting yourself out there too so that people can get to know and trust you because when you do that, now they know more about you and they want to work with you. So that's just something important too. I think when someone's looking at starting a new business that sometimes you have to put the obstacle, sometimes you have to put yourself out there when it's maybe not as comfortable, but it's important. It's important to do

Kim (34:36):

Because I feel like we're in such adjacent businesses, it's never comfortable. I think that's the other thing, everybody's waiting for the moment. They're like, I'm not ready to market myself. I'm like, if you're trying to get clients, you're ready to market yourself. And in fact, you should have started six months ago, but that's okay. The best time to plant a tree was one year ago, and the best time to plant a tree second best time is now. I think that no one's ever ready. And so I think the obstacles sometimes, I think to what you're also related is mental obstacles, and we have to break through those. I have so many clients who just don't want to be on camera, but it's not that they're, it's not really about the camera, it's about the negative messages that they're hearing in their own head, and they're worried they're going to receive negativity from the outside world and nobody messages you and is like, what a terrible video. What a terrible photo. They're actually like, oh, look, who's online. Nobody's judging us in the way that we're so worried that they are, and I think a lot of that obstacle is in our own heads that we don't feel good about things. We don't feel good about other things that are happening either internally or externally, and you have to break through those obstacles to be ready to put yourself out there if you want that, if you want that for your job and you want that for your career, you want that for your business.

Alissa (35:40):

Yeah. It's the imposter syndrome, and so it's important, like you said, to break through it and to pull out that moxie, that courage, because we all have it. We just have to sometimes dig a little deeper to find it, to get it, but then once you do,

Kim (35:55):

Then you're unstoppable. But I think I liked what you were saying about the photo shoot, about making people feel comfortable. I think that people find that community and that comfort both in when they're doing headshot or video work, but also in those communities and putting yourself in the right place to feel ready for it. I think so much of this is mental, and it's hard if you're putting yourself out there, but your peers or your family have private lives and you feel like you're the only person being more public and being more vulnerable. It's challenging. So I think that's the value of those networking groups. I know you and I met through Entrepr, and I think the value of those networking groups is it's a group of like-minded people all breaking through those obstacles together, and I think when we're all cheering each other on and saying, you can do this and you don't need to hide, I think that's very powerful as

Alissa (36:38):

Well. Oh yeah. It's so important to be part of a group that lifts you up.

Kim (36:43):

Yeah, absolutely. Absolutely. Alright, Alissa, this was so great. Where can people find you allaboutheadshot.com?

(36:50):

All about headshots with an s.com? Yes. Great. I was like, I must have listed it, but that's great. Alissa, this is such a great interview. Thank you so much. Thank you. Thank you. Thank you for joining us. Don't forget to exit the grind and enter success on your own terms. This is the exit interview with Kim Rittberg. Don't forget to grab my free download, how to Grow Your Business with Amazing video at kimrittberg.com and linked out in the show notes. I love to hear your feedback. Make sure to submit to me what you learned from the show and how you are crushing it on your own terms. Connect with me on Instagram or LinkedIn at Kim Rittberg, R-I-T-T-B-E-R-G. And this show is edited by Jillian Grover and produced by Henry Street Media. I'm your host and executive producer Kim Rittberg.

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