6 Suggestions to End The Year Right

Jessy Grossman is a long time entrepreneur in the digital media space. She’s passionate about supporting women in business and being at the forefront of innovation. She’s been quoted in Forbes and was awarded a spot in the “Influencer Top 50” by Talking Influence. In less than two years she created one of the fastest growing talent agencies in the country. Amidst unprecedented growth, she sold the multi-six-figure agency and pivoted to focus on her long-time passion project: Women in Influencer Marketing (better known as WIIM). Founded in 2017, today WIIM is the premiere professional organization for those who work with influencers. The community offers networking and new business opportunities, career services, continuous education and more. Jessy also does consulting, advising and influencer marketing recruiting with her company Tribe Monday. You can find inspiring stories and more about Jessy on the WIIM Podcast. Check out iamwiim.com and tribemonday.com for more information.



[00:00:00] Jessy Grossman: The people that you do have in your life that truly mean a lot to you, I think that you should express that to them. It’s a really powerful thing and I highly recommend it.

All right, kids. I’m back with a new episode this week. I guess I should start with like a fun life update. Hold on. Ooh, if you’re watching on YouTube, it’s not centered, but You can see my engagement ring because I got engaged this past weekend. I wish I could show you the face of my handsome fiance instead of, I mean, this ring is gorgeous, but it’s a little bit more meaningful.

to have him versus the ring, but he’s upstairs working. I asked him, I was like, so maybe you can come on the podcast. I’m like, talk about how you planned the engagement. And like, I don’t know, we can have like a fun personal episode. He seemed open to it, you guys. So maybe we’ll have that in. The not-so-distant future, but yes, I got engaged this past weekend.

I can share more about that story another time. But yeah, guys, like I’m 36, like I’m no spring chicken. This will have been my first time getting engaged, my first time getting married. We are taking the more modern approach in that, you know, we’ve been together for like over five years.

We already own a house together and we’ve been trying to have kids for over a year now. So,  while it was a little bit, I guess, of like a formality, I didn’t want it to feel that way. And I told him, I was like, please just make it special. And he hit it out of the park, you guys. Like, he truly did.

I will give credit where credit is due. I love you, Paul. And thank you for making a really special evening. So,  oh, and then we told Zoe yesterday when she got back from her mom’s. So,  she’s very excited. He asked for her permission, you know, is it okay if, if I ask Jesse, to marry me?

And she said, yes. Thank goodness. Oh my God. Okay. So this episode. is going to be a, I mean, I think it’s fun. It’s going to be a fun one, you guys. It’s about six suggestions from Moi to end the year off right. Okay. So I’m just very cognizant that it’s like the end of the year. I mean, we’re recording this before Thanksgiving.

This will come out after Thanksgiving, the Thanksgiving holiday time. And I think that a lot, I can imagine a lot of you guys are in a similar place that I’m in, which is like, I’m trying to like to assess what do I want my 2024 to look like, to feel like. I thought, okay, so 23 is my lucky number. And so I remember very vividly this time last year being like 20, 23 is going to be my jam.

Like I’m just going to kill it. Well, I know I’ve mentioned a few things on this show about how. Oh, well, it was the exact opposite of that. It was like a shitty year, but it’s, it’s, you know, I’m excited for next year because it can’t get any worse than this. The engagement is hopefully going to parlay into.

you know, even bigger, better, wonderful things in 2024.  and I know that I’m sure you guys are also sort of imagining what will 2024 look like, but I always like to take the approach, like less of the world is going to happen to me and more let’s architect our lives. Like, let’s build it together. If you want something, make it fricking happen.

So these are just six suggestions of things that.  I have found have like really improved my life, really made me feel good, and things that I want for you guys. Take them or leave them, but I do hope you consider them because I do think that they’ll be helpful. All right, let’s get into it.

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Visit me at wim.com/join. That’s I-A-M-W-I-I m.com/join today and I look forward to seeing you more around the community. All right, so we are starting hot with something. It’s very, I don’t know, practical. Tip number one, invest some money in the stock market. Okay. I know I’ve mentioned this a couple of times before.

I am, I’ve never been comfortable with like all things money. I think that I had like weird money things growing up that like my dad made so much more than my mom. And I like going from house to house and I, I think it left me like. I feel weird about money. I know I’m not alone. A lot of people feel weird about money, but I’m always one to want to challenge myself.

I feel like the more uncomfortable I am, the more I’m like, Ooh, I got to push through this. Like, Ooh, I got to figure this out. And so that, that.  that was harder for me for money, but I feel like I’ve made progress. So this past year I hired a bookkeeper, I hired a new accountant, and,  I have learned a lot from them and I’m not going to go into the specifics of that certainly, but I think that the biggest piece of advice I can give you is like.

Just exposing yourself to these things like the stock market and investing and, you know, 401k and whatever, like it will just make you feel more comfortable. And simply, if you have a better comfort level, you’ll just. You’ll do it more and you’ll, you’ll get better at it. And it’s all a process. So for me, I’m starting in a place where like, not comfortable with money.

Like, what do I do with my money? I like it, I don’t know. I’m mostly, I think it was just me being in my head and like, just. Just feel insecure about it. That’s probably the main thing I can convey, but this past year in particular, I like opened up an Ameritrade account and I started trading and I started making fricking money from it.

You guys, it’s a, I certainly am no expert. This is not going to be a conversation with money advice because I’m probably the least qualified to give it. But again, just like. Putting yourself out there and like investing in your future is such a fricking powerful thing. We’re all on the same journey to learn keep learning and grow.

And like, I’m not an expert and I fricking did it. So you can do it too.  Ameritrade is fine. There are other apps out there, but that’s the one that I use. And I have made a few thousand dollars, like probably tens of thousands of dollars already. And I just purchased stocks of products that I genuinely like and use.

Like there’s, for me, there’s no science to it, but for me, it makes a lot more fricking sense to have my money. Parked in, you know, in the stock market or in a 401k, which I contributed to a lot this year. I’m going to probably max it out. And I have a SEP account, which is a whole other conversation, but there are different types of retirement accounts.

If you are self-employed versus employed by someone else. So if you’re self self-employed, definitely check out a SEP retirement account. But anyway, it’s the week that makes way more sense for me to park my money in places like that. Then in my checking account, I’m making pennies on the dollar. Okay.

Suggestion number two, open up more. I gotta say, this was a very transformative year for me. I usually am very uncomfortable opening up to people. I acknowledge that, like, mainly through WIM, I have hundreds and thousands of, of mostly women who like follow me and were, you know, connected and maybe they listen to the podcast or they’re part of WIM and like, for all intents and purposes, it seems like I have a community.

Here’s the dirty little secret. Real, like, personal friends who really, truly know everything about me, like the good, the bad, the ugly, everything. It’s like one person, like I have like one best friend and not many other real friends. If I’m being completely honest, I also have like a very small family, I have a lot of family issues, like being estranged from most of them.

I have like. Very few people who I consider myself comfortable with, like truly, truly comfortable with. I only bring that up because, in this past year, I’ve tried to make a concerted effort to just open up more to be like unapologetically me. It’s going to sound stupid. Sometimes it’s going to sound unintelligent.

It’s going to sound silly. I’m going to trip up and it’s not going to be perfect, but opening up to people and just being. Being more comfortable being myself has been fricking therapeutic. So I highly recommend it to you.  what I will warn you about is that in doing so you might rub some people the wrong way and you might, like some people might not like what you have to say when you’re being more and more honest.

So we do want to warn you that that is a very real outcome, but even with that. I, I still feel like I’m like the honesty in it like trumps the, you know, embarrassment or the, you know, the shame or like whatever it is, because there is no shame actually when you’re just being honest, it’s like, well, this is who I am.

And if you don’t accept me who I am. You know, like, we can disagree, but if you don’t accept that, like, this is what I believe and respect it, then you’re probably not a person that I would want in my life anyway. But these are things that you have to practice. I think that’s what I want to convey to you guys, like, opening up more, like.

At least for me, it has taken a lot of practice to be able to do and do consistently and feel more and the benefits of doing so regularly have felt good. Okay. Suggestion number three, I suggest that the people that you do have in your life, truly mean a lot to you. I think that you should express that to them and tell them that you love them or tell them that they mean a lot to you and tell them why.

And like, I feel like for some of us that feels awkward to do or it’s just like not our natural way, but it’s really important. And You’d be pleasantly surprised, I think, that by expressing those things to people who mean something to you,  you build more trust with them and they’ll say kind, honest things in return.

And I think that’s been a theme this year for me is like just really being, wanting to deepen relationships. Again, I’m not someone who has a ton of them, but the few that I do, I want to. Have those be like deeper, more meaningful relationships. So expressing how you feel about people and complimenting them when you feel like they have, you know, earned it or deserve it or whatever it is.

It’s a really powerful thing and I highly recommend it. Okay.  suggestion number four, I really believe that you need to spend more time with animals. Yes, you heard me. Animals, I have a cat and a dog, and some of the most stress-free moments in my entire life have been when I’ve been like snuggling the crap out of my dog or like really snuggling with my cat.

He has been waking me up at like four in the morning lately and it is simply. just to snuggle. And this cat purrs loudly. Like he is no dainty flower. This cat, like he’s a bit of a tank and he purrs very loudly. And if I wasn’t so fricking in love with this cat, I’d probably be annoyed at four in the morning to be woken up just to snuggle.

But I snuggled back. Why? Cause he’s just, he’s so amazing and he’s so sweet. And it’s just like all of the chemicals that I know are being released into my body simply because I’m like being affectionate with my animals, my pets. It’s just, that it’s like a wonderful thing to have in your life. So if you don’t have an animal either, I highly recommend getting one.

But you’re probably like, some of you at least are like, Jess, I don’t have the time. I’m busy and I wouldn’t be able to give a pet a good life. So I can’t get one. Here’s what I recommend instead. You should look into fostering. And if you’re in New York, I’m more than happy to tell you about a couple of organizations that I’ve personally fostered with that,  would love more fosters.

We still foster every so often because I mean, if it were up to me, we’d have like, 10 dogs and 20 cats. Okay. Maybe not, but we would have a lot and I do love fostering and it’s a temporary situation. So you could have a dog or a cat, some sort of pet in your life for like a month or less. It’s the most incredible experience and I highly recommend it.

Also, that’s how we got Jojo. She was my foster fail. And so it’s also a great way to like shop for a pet because if you love them, you can keep them and quote-unquote foster fail. Okay. The second to last suggestion, number five to end the year, right? Find more of what you enjoy and do it more. I don’t know about you guys, but I have struggled this year when reflecting.

Like, what do I enjoy? Like what genuinely makes me happy? And I think that maybe the reason why I was struggling with it this year is because I think that some of the things that used to make me happy and get me excited aren’t doing it for me anymore. So I don’t know, again, I’m like 36.

So like, maybe it’s like a shift in. in life, like different life phases or whatever it is. And I feel like that’s going to happen multiple times more throughout my life, but perhaps like every 10 years or so, like our, our likes change. And I think that that’s natural, but I. I don’t, I mean, I never really thought about it before, so I was like a little bummed when I couldn’t think of things that like genuinely really made me happy and excited because I was doing these things that I was so used to doing for so long and I wasn’t like getting the same fulfillment out of it.

Um Maybe you guys know this already and maybe I’m just dumb, but I honestly, like, I, I never really thought about it. And so I was just going through these motions of doing the things that I used to enjoy and like not getting fulfillment from it and like feeling kind of shitty about that.

Right? So I have learned, for example, silly example, that I enjoy puzzles. I know this probably sounds silly. So lame, but it’s so true. I have enjoyed like, okay, so we have this buy-nothing group in New York and Brooklyn that I’m part of. And I’ve gotten three or four puzzles from people who gave them away.

And I just got one the other day and I’m like genuinely excited to find some time to do it. Um. I also used to enjoy baking so much, less though the baking, I guess, and more so like the decorating of cakes. And in my mind, I want, I still do think I enjoy giving the finished product to somebody and like having them be like, Oh my God, this is me just for me.

I feel so special. Like I love giving somebody that experience, but it takes a lot. of time to bake. And I just like haven’t been so into that. Also was in a phase for a while where I genuinely enjoyed cooking. I was like really into keto and I was finding all these like new recipes to do. This was probably like five years ago at this point.

Wow. Time flies. And now I’m just like, I like making the same sort of things. You sort of have to be in the mood for it. But anyway, the point is that your likes are going to shift. And if you’re maybe in a rut for a bit, like I was like, Do some critical thinking to say like, is it that I’m just on a rut or maybe I just enjoy different things, but that could be a scary proposition.

Right? Because then you’re like, well, like, what do I enjoy now? Like what makes me happy? And I do think that it’s really important to sort of reassess those things and like, ask those types of questions, you know, every five years or every 10 years and see what your answer is. And, then do those things more.

Okay. The last time. Suggestion to end the year right, eliminate stuff from your life. So you can, you can interpret this in a few different ways, right? Like for me, I hate things. I’m not like a things person. I love throwing stuff away. I hate. Like paper. I love having everything like electronics. I can organize it better.

Like if you ever have kids or you have kids, you understand, like having these little, like, Oh my God, these like cheap little like toys and tchotchkes and whatever, like constantly all over the house. Like I can’t stand it, but then I feel. Guilty if I throw it away so that we have like a whole system of like, you know, go through the stuff, clear out the stuff so that we can get rid of some of it.

Cause it becomes overwhelming. Anyway, I’m not a stuff person. I like to enjoy having a pretty minimalistic house. All that being said, sure. Eliminate the stuff, the physical stuff from your life, because lack of clutter does, I think, make a big difference for me at least. And hopefully for you, but also.

The stuff that we’re filling our time with, that’s probably what I mean most. And that’s the part I want to focus on with you guys I think that eliminating the superfluous stuff in our lives just frees up so much more time for you to do what’s more meaningful to you. So for example, even in my business, let’s bring it back to business.

This year has been insane. We planned five huge tentpole events in different cities around the country. One every couple of months, right? Throughout the year. Cause our last one was in October. It was a busy year and there were parts of that that I loved and I enjoy and I enjoy the planning aspect of it and seeing it come to life and all that, but I gotta say.

The past month, I cut it off. I downshifted after that event in particular, and I’ve had all of this additional time towards the end of this year to sit and reflect and think of like what I want to be doing in 2024 and like big picture thinking and just like opened it up to Do whatever I want in my business and not be so bogged down with so many things going on.

Anyways, it’s been nice and like really noticeably different. So if you are in a position where you can just eliminate some clutter, whether it’s like emotional or physical or, you know, calendar clutter from your life, You start to feel the difference. And I do think that that would be a positive change to end the year on a good note.

So with all that being said, guys, I thank you for listening. I hope that you got something from this, you know, take some of it, take all of it, leave the rest, interpret it how you want. But I do hope that it helps you for the rest of the year. Speaking of the rest of the year, we do have. One event that I want to remind you guys of, it’s our annual State of the Union.

We have it that it’s happening virtually every single year. We did it last year as well. We have incredible panelists who are coming to chat with you basically to reflect on how 2023 was and also make a lot of predictions and anticipate. 2024, sort of saying that the union is on December 6th at 1 PM Eastern, very excited about it.

And I hope you guys attend for members. Of course, it’s always free. So I highly encourage you to check that out. I hope to see you there. And I hope to see you next week for another episode of the Wynn podcast. All right. Take care, everyone. Happy holidays. If you enjoyed this episode, we gotta have you back.

Check out our website for more ways to get involved, including all the information you need about joining our collective. You can check out all the information at IAmWhim. com. Leave us a review, or a rating, but the most important thing that we can ask you to do is to share this podcast. Thanks for listening. Tune in next week. Tune in next week.


Founder of Women in Influencer Marketing and CEO of Tribe Monday

Jessy Grossman is a long time entrepreneur in the digital media space. She’s passionate about supporting women in business and being at the forefront of innovation. She’s been quoted in Forbes and was awarded a spot in the “Influencer Top 50” by Talking Influence. In less than two years she created one of the fastest growing talent agencies in the country. Amidst unprecedented growth, she sold the multi-six-figure agency and pivoted to focus on her long-time passion project: Women in Influencer Marketing (better known as WIIM). Founded in 2017, today WIIM is the premiere professional organization for those who work with influencers. The community offers networking and new business opportunities, career services, continuous education and more. Jessy also does consulting, advising and influencer marketing recruiting with her company Tribe Monday. You can find inspiring stories and more about Jessy on the WIIM Podcast. Check out iamwiim.com and tribemonday.com for more information.

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