200: Why It’s Important to Celebrate Your Wins with Jennine Heller

Andrea Liebross: Welcome to the She Thinks Big! Podcast. Get ready to level up your thinking and expand your horizons. I’m your host, Andrea Liebross, your guide on this journey of big ideas and bold moves. I am the best-selling author of She Thinks Big: The Entrepreneurial Woman's Guide to Moving Past the Messy Middle and Into the Extraordinary.

I support women like you with the insights and mindset you need to think bigger and the strategies and systems you need to turn that thinking into action and make it all a reality. Are you ready to stop thinking small and start thinking big? Let’s dive in.

Hello, my friends, and welcome back to the She Thinks Big! Podcast. I am not going to make this intro very long, but what I do want to share with you is that today I am chatting with a fellow masterminder, Jennine Heller.

She and I are in a group together. We have the same coach, so we get to see each other regularly, and she and I celebrate together. So this is the 200th episode of the She Thinks Big! Podcast, which used to be Time to Level Up for the first 100 and something episodes. But this is the 200th.

When I was thinking about, “Hmm, what do I want to do for this episode?” I thought about, “Huh, I need to have someone in here that celebrates with me on a regular basis.” Sit back, buckle up, and listen to my conversation with Jennine.

Hi, Jennine. I'm happy to have you here. How are you today?

Jennine Heller: Hi, great. Hi, Andrea. It's so nice to be with you today. Thank you.

Andrea Liebross: All right. Before we get started on our discussion about celebration, tell the audience who you are, and then I will tell them how we know each other. How does that sound?

Jennine Heller: Great. That sounds perfect. I am a no-nonsense executive coach for leaders in tech. I was a software engineer. I moved into management. I co-founded and sold a software company, and I held several executive positions, so I bring decades of hands-on business experience to my practice. My passion is working with tech leaders to understand their deepest values and strengths, set bold objectives, and lead with true confidence.

Andrea Liebross: I love it. Okay, what was the very first thing you said?

Jennine Heller: I'm a no-nonsense executive.

Andrea Liebross: I think this is why Jennine and I get along so well. I feel like I'm sort of no-nonsense too. I'm not coaching tech executives, but I'm coaching other people. She and I are in a Mastermind together for a couple of years now.

The reason I invited her on today, my friends, is that this is the 200th episode of the She Thinks Big! Podcast. Actually, the Time to Level Up turned into She Thinks Big! Podcast. My podcast producer and I, Stacey Harris—I have like 72 Staceys in my life—but Stacey Harris thought that we should talk about celebrating in this 200th episode.

So, as I started to think about how did I want to share this with you, how did I want to create a discussion around celebration, I thought of Jennine because every time we get on a mastermind coaching call, our coach—a different Stacey, who I've had on this podcast—always starts with, “What are we celebrating?”

That's our first question. “What are your wins? What are we celebrating?” So I have been celebrating with Jennine now for several years, multiple times a month. I thought she was the perfect person to come on here and have this discussion.

Jennine Heller: Sounds great, absolutely. I think so, and you have a lot to celebrate and sometimes you need reminders.

Andrea Liebross: I do, and Jennine is very good at reminding me. She actually would give me a little hard time there sometimes when I was like, “I don't know what I'm supposed to celebrate. I don't know what I'm celebrating.” I'll say, “You go first.” And then she goes first and then I ponder and then I get to myself. But yes, you do have to push me a few times.

Jennine Heller: Yeah, little no-nonsense nudge.

Andrea Liebross: Yeah, all right. So, Jennine, what are your thoughts about celebrating? Tell me all the things and then we'll get into this.

Jennine Heller: Well, it's funny because when you are an ambitious person, you're a high achiever, you're busy, you're getting stuff done, sometimes you think that celebrating is maybe a little self-indulgent. But in reality, it's necessary. It's actually something that you have to do.

Andrea Liebross: Right.

Jennine Heller: It's not an indulgence. You have to make time, you have to develop a practice and you have to really embrace the idea that celebrating is part of how you manage your mindset as a business owner, as an executive, as you go about getting your stuff done.

Andrea Liebross: So true. I think that it does have to become a practice. One of the things in planning for this podcast, I was like, “Okay, how am I going to structure this?” The first thing that I wanted to share, and Jennine just brought up, is that it's so necessary for us to have a routine or build in a habit or have space to “celebrate” on a regular basis.

Our coaching calls do serve for me that it does serve as that space to do it. I sometimes will do it when I'm planning my week and reflecting on the past week. I'll do it then. But the coaching calls you actually are verbalizing it, which is totally different, to actually say it out loud. I think that's different too, than just writing it down.

Jennine Heller: Yeah. There could be something that you do with friends or colleagues or if you think about people who are supporting you in your business and your life, you can have just when you see people for lunch or coffee, it could be something that you say, “Let's all make sure that when we get together, we do this.”

The other thing about celebrating is it doesn't have to be about big stuff, it should be about almost anything that is positive. It can be a big thing, it can be a little thing. The type of celebrating you do can be in relationship to that.

I had a client who went out and bought herself a very expensive piece of jewelry for a promotion that she had been wanting to get for a long time. That was her way of celebrating. I think that that celebration was commensurate, but that's not what you're going to do every time.

The other thing is to celebrate things that aren't just about your business. Like if you get the kids off to school in the morning with a little fuss, you know what? That's a win. It's big and small. It's all different ways. It's about establishing a regular way of doing that.

Andrea Liebross: Sometimes when we come up with our celebrations, you are always saying, “I went on a hike.” Like you got outside, you spent time outside, that can be a celebration.

Sometimes I like to celebrate the fact that I actually took time off with not working, and not even looking at any of my ways I'm connected to the world, that can be a celebration. It doesn't have to be like, write a book or 200 podcasts. Actually, let's think about this. Who says what's small and big? That's almost like societal in a sense, too.

Jennine Heller: It is. I think that when you're trying to achieve, you have this idea of should, you have this idea of what matters and what doesn't matter and you're always looking for the big rocks. But they don't just happen. They happen by step by step by step, you have to move the little pebbles before you can move the big rocks.

Every step you take that gets you towards your goals is a win. Those steps can be in your personal life creating space for yourself, creating energy for yourself, getting a good night's sleep, or they can be in your business, the fact that you made a hard decision.

Sometimes I have people who move from doing to managing and they have to learn that their presence in that day made things not as bad as they could have been. They don't have anything to point to, but as a business owner, sometimes your level head and your prioritizing and your good decisions just made things a little bit smoother than they could have been. That's a win.

Andrea Liebross: Totally true. I did a little Googling and I typed something like, “What questions can you ask yourself when you're trying to figure out things to celebrate?” Brendon Burchard and he had these six quick questions, which I think totally speak to something like going from being the doer to the manager.

He said, “Ask yourself, “What did I do well this week? What did I achieve? What went well this week? What good things happened that I didn't even anticipate? How can I feel good about something that happened this week? What could I notice that happened that brought me joy, fulfillment, or a sense of accomplishment?”

So what could I notice? There are a couple that say, “What did I do well?” Or, “What did I achieve?” Then there's the general, “What went well? What good things happened?” Then there's the piece here about, “What did I notice?” I just thought that was interesting. I really like those questions.

Jennine Heller: Yeah. It comes back to being mindful.

Andrea Liebross: 100%.

Jennine Heller: If all you're doing is trying to chase that to-do list, trying to get your tasks done, you're not even noticing what's going on and sometimes we're focused so deeply, hey, that's great when we're in execution mode, but sometimes you need to take a step back and say, “What's the effect? What's the impact of what I'm doing? Actually, is this where I want to head?”

Andrea Liebross: Yeah.

Jennine Heller: The other thing that I find so interesting is that when we are in execution mode, and it's just all the time, we become slaves to our list, our tasks, they own us, we get into this mode of like, “What do we need to fix? What's missing?” You get it done, done, done. You don't even stop to celebrate that or acknowledge it and you're just going on and on and on.

Now, when we get into that flow, that's not always a bad thing. Sometimes that's great for our execution and getting things done. But the thing is that we are not to-do lists. We cannot treat ourselves like to-do lists and say, "I did this. I did that. Done, done, done." No, we actually have to stop and say, "And I did something great. And I'm going to acknowledge myself." Because we are not our task list.

When we acknowledge ourselves and when we celebrate, we actually get in the moment, we stop executing, we look at what's going on, we actually generate energy by being positive about something, we slow down, we celebrate it, and it gives us energy to do more.

It helps us look at the future, instead of grounding in what's next, what's next, or what didn't I do. It really helps us be open and forward-looking and gives us as people energy. We are not our to-do list.

Andrea Liebross: No, we're totally not our to-do list. I think when I'm coaching my clients, I'm really big into, “How did this feel?” This really has to do with feeling the win and not just doing the win, in a sense. Because there's the to do list piece.

I think if you can feel the win, it really allows you or feeds into more confidence. That's a confidence generator, being able to feel it. I have an example of that. When I finished my book last September, actually, this was probably maybe four or three or four months before, I knew the release date and I was on a coaching call, a mastermind call with Jennine and someone, either you or Stacie said, "Are you going to celebrate this? Are you going to have a party? Are you going to do a launch?"

I said, "I don't think so. I don't know." Now at that point, actually this is interesting, I was so into the to-do list of all the things that had to happen in order for it to actually launch, that I couldn't even go to that place where I might actually feel a win.

Now that I think about it, that's probably why I was like, “No way. I can't do that.” But they pushed me.

Jennine Heller: And I had I literally yelled at you.

Andrea Liebross: You did yell at me, yes. Then I ended up having a fabulous big party, a launch party, which I'm so glad I did because it was really when I felt it. The to-do list is never over, let's face it. But no, the to-do list sat on the side. That wasn't what I was focusing on. I was really focusing on being in that moment and feeling what that looks like and feeling it physically almost in a sense.

Jennine Heller: Yeah. Having those moments allow you then later to say, “Remember what it felt like.” You can reconnect with your success. The more you have those moments where you really just marinate in the happy, you can then access those later and it builds.

Andrea Liebross: It totally does.

Jennine Heller: The other thing that is really interesting is that sometimes people use fear as a motivator. I've got this to-do list and I've got so much to do and it's like unless you really create pressure for yourself, you're worried that you're not going to get it done.

Sometimes people do not want to celebrate because they feel like I can't take my foot off the gas pedal. The reality is you need to take your foot off the gas pedal, you need to feel the success, or you're going to run out of energy.

You need to find a different motivator. If fear and pressure are the only things motivating you, this is not a sustainable effort. This is not a sustainable business. You have to actually use your success and the party and the toast with your friends and supporters. Ultimately, the goals and the results and the impact you're having on your clients, those have to be your motivators, not fear and pressure.

Andrea Liebross: That is interesting because a lot of people do use that fear. We can all use it. What if this doesn't happen, then what? I like to say this serves as evidence that you can get through things and that you do have something to offer, whatever it is. You are able to not work for a day and the world still survives. Yeah, what fear can be a motive? This is a much better motivator than fear.

Jennine Heller: A much better motivator. And if you're just working, working and never celebrating, this is back to the mindfulness thing, you're going to wake up in five years and say, "Why did I do any of this?"

Andrea Liebross: Yeah. Why did I do it? I don't think if you don't celebrate and you keep plugging away at that to-do list, then you don't set yourself up for bigger goals either. Do you find that?

Jennine Heller: Well, it is very backwards-looking, whereas the celebrating provides that energy and that positivity and that possibility forward-thinking. You need that as a business owner, as somebody who's really working towards having an impact. Isn't it nicer to show up in the world with that happiness and that joy and that confidence and satisfaction than the stress?

Andrea Liebross: Yes, 100%. Learning how to also, I think this is another thing, learning how to share with others the celebration is very important because that creates energy not just in you, but in other people too. I think sometimes I feel like I'm doing them a favor by including them in this celebration, because they get to have that little boost of dopamine too.

Jennine Heller: Mm-hmm. No, absolutely. I mean, think of that person in your circle of friends and your family and your professional life who's just a ray of sunshine. Now, that might not be how you wake up in the morning. But when you bring little rays of sunshine to the world around you, it reflects back.

There's a great aspect to the energy you bring, and then what it brings you. If you're just always stressed and grumpy and heads down, that's fine to get when you're in execution mode, but you have to get out of execution mode, you have to think about why you're doing stuff, connect with your motivation, and then celebrate the things that get you towards that, then it's just going to feel so great as you really approach that and achieve your goals.

Andrea Liebross: If you can't celebrate with someone else. If you always feel like you have to make yourself smaller, we'll call it, or not bring things to the surface that you're actually excited about, then I think you're also not in really a good relationship with the world around you.

Jennine Heller: Oh, that's interesting.

Andrea Liebross: Right? If you're not telling other people what you're proud of, or what you've accomplished, or what you've achieved, big or small, then you're not really playing fairly in a sense. You're scared of how other people are going to judge you or you're minimizing how far you probably could go.

Jennine Heller: Well, I think people, this is one of the things that makes it difficult to celebrate. One is you feel like I can't take my foot off the gas pedal or I don't have anyone to celebrate with or whatever it is. But the reality is that a lot of people confuse being proud of something with being arrogant.

Andrea Liebross: Oh, yeah, let's talk about this.

Jennine Heller: Yeah. When you achieve something that you have wanted and even if it's a small step towards a larger goal, that's great. To share that with other people, even to acknowledge it to yourself is hard for some people because they feel like they're being arrogant.

There is a difference. Arrogance means that you think you're better than other people because of it. Happiness and being proud means you're happy because of it. Those are two very different things. You can be happy about something and not truly believe you're better than other people because of it.

Andrea Liebross: That's so true.

Jennine Heller: I have my hairstylist whom I love and I've been seeing her forever and she's relatively young and over the years, I've seen her grow in the business and now she owns the salon.

Andrea Liebross: That's so good.

Jennine Heller: I didn't know that for almost a year because she didn't say anything. When I found out, I said, "Why didn't you tell me? I would have taken you out for a drink. I would have high-fived you. I would have something." She said, "I don't want to brag."

I actually thought that was a little sad because she had worked towards something. She was amazing at what she did. It felt to me like there should be a way for her to share that without feeling bad about sharing it.

This was when you're getting your haircut, it turns into one of these discussions. We work on this the whole session. She does now, actually, she committed to telling five people that week.

Andrea Liebross: Okay, that's so good. Do you find that men are different than women on this?

Jennine Heller: I think they've been socialized to be more open with the things they've done. I don't think, and it's interesting, my practice is made up almost half and half.

Andrea Liebross: Yeah, I know, that's why I wanted to ask you that.

Jennine Heller: Everyone's pretty senior. What's interesting is the introverts and the insecure people are pretty balanced across genders. But I think that men and women are socialized to express these things differently. I think men are encouraged to still vocalize and to say the good things.

Now, some men who are insecure about it, that doesn't feel comfortable for them, but they still feel like they should do it. Whereas women, I think, are socialized to just hide it. I think there's an awareness of, we haven't talked yet about how to really turn this into a practice, but it starts with thinking about who are your people who support you, who's going to love you, who's going to high five you and start to think about those people that are your real supporters.

It can be in your personal life, it can be in your professional life, your family, whatever and start with those people. If you find it difficult to celebrate, start small and find a way to share with them and find a way to get that high five and to get that applause. Then you can start to expand your circle.

A lot of it starts with your mindset. It's that mindfulness of “Was this a small step I took towards something bigger and I'm happy about it?” Then maybe you give yourself a little pat on the back.

Andrea Liebross: It just has to be a step too. It doesn't have to be the grand finale. Okay, so in practicing, how do we turn this into a practice? I do think that's a great piece of advice to start with a small group of people, identify who they are. Do you have the next step?

Jennine Heller: Yeah, think about things that make you even happier. Like for my client I mentioned, it was a very expensive piece of jewelry. Okay, great. It could be taking the afternoon off. It could be having a food treat. It could be watching a show that you absolutely love, it could be putting on your favorite song and dancing around the room.

Andrea Liebross: You're good at that.

Jennine Heller: I love to do that. I absolutely love to do that. Yup. I don't even put on my earbuds. I put the speakers on in the house.

Andrea Liebross: I do too. That's so funny. In this new house, we have this really good sound system and I have been known to turn the music up really loud.

Jennine Heller: Really loud. Yeah, because then you can dance like all of them.

Andrea Liebross: Yes. Yes, that's so funny.

Jennine Heller: Yes, think about you're already happy about something, so what makes you even happier? How can you even go towards that happiness?

Andrea Liebross: That's good. That's good. Yeah.

Jennine Heller: There's another couple of things that I think are important. One is to turn it into like a physical manifestation, like something you write down or a picture you put on the wall so that you can look at it and remind yourself.

There's the moment, there's the ephemeral moment of the dancing but then maybe there's like a picture. I bought a picture at a yard sale once because it reminded me of something in my past that made me super happy. It was of a place.

Sometimes I look at that and just think of all the happy times I've had, I try and connect them. Sometimes I look at that picture and it allows me to just be happy. So looking at things or making a list or a sticky note or an attaboy or whatever it is that is up over your desk and going, "Look what I did last week," or an exclamation point, it almost doesn't matter, but something that you can look at or touch or hear that connects you with that success is really a nice thing to do.

Andrea Liebross: Love it. Okay. Any other great tips? I mean, something that I've thought about is like inviting people into your celebration versus celebrate. I think there's equal importance to invite people in and to celebrate on your own. I think sometimes we don't want to take the energy to invite people into our celebration because it's like another thing on the to-do list.

Jennine Heller: But that's why I think you start with your group, and then expand it out, and maybe even your group can help organize things for you, or have a little lunch for you, or whatever it is.

I guess the other tip you're asking me, and I had to think about this for a second, but it's really nice to collect your wins, and to think about your celebrations, and to retouch that thing.

Whether you have something on your wall or a piece of jewelry or a picture or whatever it is, every time you celebrate, take a minute and think of all the wins. It's not just that day. It's like, “And last week I did this and the week before I did this. Last year I did this and today I'm doing this.” I'm like, “Well, there's a lot of really positive stuff along the way.”

Andrea Liebross: Along the way. Yep.

Jennine Heller: Along the way. Connect them all. Actually, I think the more you do that, the easier it is so that when you're in a positive space, like all the positive stuff comes back to you. It's just not that day.

Celebrating, it doesn't just make you feel good in the moment. It really does reground you in your purpose. It does make you feel good about what you're doing and reminds you of your reason for getting up in the morning.

Andrea Liebross: A hundred percent, a hundred percent. It regrounds you, it reminds you why you're doing it. People say, “Why do you do what you do?” a lot of us start with “I do it because I want to X, Y, and Z for other people.” But part of why you do what you do is hopefully it's helping you feel great too at the same time. It's not always about everybody else. It can be a little about you.

Jennine Heller: It can be a little bit about you. In fact, if you just are very self-negating all the time, you're going to run out of steam because building a business, building a career, having an impact, it's a long haul.

Andrea Liebross: It's a long haul.

Jennine Heller: It's a long haul, it's not an overnight thing. If you are not taking care of yourself, and I don't just mean like eat well, whatever, if you do not recognize yourself and celebrate yourself, you're going to run out of steam. You just start.

Andrea Liebross: You are, 100%.

Jennine Heller: Yeah, that's why it's a necessity. It's not an indulgence.

Andrea Liebross: Yeah, that's not an indulgence.

Jennine Heller: It's not an indulgence. You're not going to run out of steam. In fact, you better take your foot off the gas pedal for a minute because the car needs to go in for servicing and you need to walk around the block. You have to do it, you're not your to-do list. It's absolutely, absolutely necessary and it's fun.

Andrea Liebross: Yeah. It's so fun.

Jennine Heller: If we're not having fun, it's no fun.

Andrea Liebross: It's no fun. It's no fun. All right, so as we wrap up all of you listeners out there, I would love to know what are you celebrating? Send me a message, message me on LinkedIn or Instagram, or wherever you are, send me an email. Tell me what you're celebrating because if you think no one will listen, I will listen. I want to celebrate with you and I think this is not an indulgence, it is a necessity is a great way to put a little bow on this.

Jennine Heller: Yeah, absolutely.

Andrea Liebross: Well, Jennine, thank you for being here for a very important discussion.

Jennine Heller: Andrea, I'm so happy that this is your 200th episode. What are you going to do to celebrate this besides have me on your podcast?

Andrea Liebross: I mean, having you as a celebration in and of itself. Well, the actual date, I think that this is going to get released—we're recording this a little bit ahead of time—is the middle of October and I am taking a little bit of time off that very week.

Jennine Heller: That’s wonderful.

Andrea Liebross: So, going to see my old friends, and they're always up for celebrating actually. So, that is a good thing.

Jennine Heller: That's wonderful. Yeah. Well, thank you for having me. This was so much fun.

Andrea Liebross: Thank you for being here. If people want to learn more about you and all of the amazing coaching you do, which Jennine is a master, my friends, so if you have anyone in your world that is in tech, that is in a leadership position, that is growing and getting to the next level, you need to connect with her, where should they find you besides Googling you and you'll pop up with having written a thousand articles?

Jennine Heller: Start with my website, jhellercoaching.com.

Andrea Liebross: All right, it's pretty easy.

Jennine Heller: I'm on LinkedIn, connect with me. I'd be happy to hear from you. Just reach out. Yeah, and Google me. You'll find me. I'm out there.

Andrea Liebross: All of this will be in the show notes. Okay, friends, keep celebrating. Tell us what you're celebrating. Seriously, I would love to have an influx of celebrations that week. All right.

Jennine Heller: What you're celebrating and how you're doing it and who you're celebrating with.

Andrea Liebross: That's true. What, how, who, where? Give us all the details.

Jennine Heller: All the things.

Andrea Liebross: All right, see you next time, my friends. Have a great week and keep thinking big.

Thanks for tuning into the She Thinks Big! Podcast. If you're ready to learn the secret to unleashing your full potential, don't forget to grab a copy of my book, She Thinks Big: The Entrepreneurial Woman's Guide to Moving Past the Messy Middle and Into the Extraordinary. It's available on Amazon and at your favorite bookstore.

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