Enthusiastically Self-Employed: business tips, marketing tips, and LinkedIn tips for coaches, consultants, speakers, authors, solopreneurs & small business owners

Side Hustle v. Jump Ship: Insights from Jenny Kay Pollock Ep 146

Brenda Meller Season 1 Episode 146

Join me as I welcome Jenny Kay Pollock, who delivered a talk at the SHIFT-LIVE-A-Thon event, "Side Hustle v. Jump Ship."

00:16 Jenny's Background and Side Hustle Journey

01:00 Leveraging AI in Business

02:48 Side Hustle vs. Jumping Ship

03:44 Evaluating Your Current Situation

04:51 Building a Solid Foundation

05:29 Strategies for Side Hustles

06:12 Scaling and Making the Jump

07:55 Financial Planning and Support Systems

09:37 Key Takeaways and Conclusion

10:10 Q&A and Final Thoughts

**************************************
My name is Brenda Meller. I'm a LinkedIn coach, consultant, speaker, and author. My company is Meller Marketing and I help business professionals get a bigger slice of the LinkedIn pie.

Visit mellermarketing.com

Let's connect on LinkedIn: linkedin.com/in/brendameller
(click MORE to invite me to connect and mention you listened to my podcast)

Speaker 1:

Today's episode is a replay of a speaker that I had at my Shift Live-a-thon event from back in April of 2024, and this is Jenny K Pollack. In Jenny's session, she's talking all about side hustle versus jumping ship, and she talks a little bit about her background, how her business came along, talks a little bit about AI in here as well, and then goes through the process of building a foundation, different strategies for side hustles, etc. So I hope you enjoy Jenny's presentation here and I look forward to seeing you on LinkedIn. We're going to shift next into our next speaker, who is Jenny K Pollack, and Jenny's going to be talking to us today. Look at this great topic side hustle versus jump ship. Jenny, first, why don't you tell us a bit about what you do, where you are right now, and then we'll get into your topic?

Speaker 2:

Absolutely by day. I used to do mobile marketing for apps and that was what I did all day and I really wanted to own my own thing, and so I was working on this Women in AI podcast and community as a side hustle and recently jumped ship. So we're going to be talking about that, what that looks like and what that means so excited to share my journey with all of you today. Awesome, perfect, thanks, brenda. All right, so I was working at this company and it was great and engaging, but I had been there for about four years and I needed a new project and something else to think about. So I started working on Women in AI, which is a podcast and community. We're an AI first business, which means everything we do we start with AI and then we work with the AI to make it better and to make it ready for everyone, for our audience. It's really a partnership between myself and the AI, and I want to encourage all of you as people who are considering jumping ship, as people who have jumped ship, as people who are working on your side hustles.

Speaker 2:

Ai can be your business partner. Gen AI can make stuff a lot easier for you. You can look at it as a business partner, another employee, a brainstorming buddy, and I think it can make the transition easier. So we're going to talk about that. When you look at AI support for small businesses, the way that I've been able to use it is really as an entry level or assistant to support anything from creating slide decks to my headshot on the first page. Instead of doing a whole photo shoot. I actually uploaded some images and had it edit that and change the way my hair was and my shirt and all of those things. You can streamline a lot of the stuff that is heavy lift and it takes a lot less time. It helped with our first draft of the website. It created our logo that you see in the bottom right corner. Anything that you're struggling with can be supported by AI. It can validate your business model. It can support your content creation. So for today, I'd like to do a prompt along. Please feel free to pull up your favorite Gen AI tool. I've been using Pyai a lot. There's also ChatGPT and Google's Gemini At the bottom of the slides. When you see the icon with the robot, that'll be a prompt that you can use to help you decide if it's time to jump ship, prompt that you can use to help you decide if it's time to jump ship.

Speaker 2:

So I want to talk about side hustle versus jumping ship. In terms of the side hustle, it can feel like you're doing so much because you're doing a job that you've been doing for a while and something new, you're creating something from the ground up, and that's so much work. And then when you jump ship, it is really enlightening because you have all this time, but actually you don't, because you're so busy building your business. And I have these two pictures here, created by AI the side hustle one. Actually, that's what jumping ship feels like as well, but it feels a little bit different because you're doing it for you and you get to focus on one thing and it's your thing. So the vibe and the environment that you're working in is a little bit different, and that's what I found from my experience.

Speaker 2:

The next thing I want to talk about is evaluating your current situation. So there's a series of questions here, and I think the first part is starting with your career satisfaction and goals. Are you happy with your nine to five? Are you learning? Are you providing value? Is it aligned with your values? Do you need the income? What's your personal burn rate and then analyzing your skills and interests as you get closer to making the move. What do you want to do? What inspires you? What are you interested in? Is their product market fit? What data do you have to confirm that? Do you need to do user research? Do you need to talk to potential clients and customers? What can you do to evaluate where you are and where you want to go?

Speaker 2:

A prompt you can use is what are the top five skills and qualifications for people starting their own at marketing consultancy? That's something that I looked into. You can put in any business there at the end, whether it is a coaching business or a marketing agency. Just put in anything you're considering there and you can build it out and it'll actually highlight the skills for you and you can see if that aligns with what you're working on. So the next piece is really building a solid foundation. You want to validate your business idea. You want to create a business plan, and the prompt that I used here is help me define my business idea and unique value proposition. I typed that into pie and it spit out four questions for me to answer, and sometimes the AI has got it right and they're great questions. You can see them over on the right-hand side here and sometimes it doesn't have the best question, so you need to, of course, use your own judgment when working with the AI to decide, because jumping ship is a big choice to be made.

Speaker 2:

I wanted to drill down and talk about strategies for side hustles because, at the end of the day, many of us start out as a side hustle and sometimes graduate to jumping ship and sometimes we don't. It depends on what your needs are. It's a very personal decision, but when you're in the side hustle phase, time management is so important, whether that's calendar blocking or reducing, context switching or even just setting a time limit hey, I'm only working on this project for this long. Then you can leverage your existing skills and network to build your new business, and the more you do that while you're in the side hustle, the easier it gets for you to get more data points to decide when it's time to jump. Next is scaling your side hustle and knowing when to make that jump.

Speaker 2:

This calculation is deeply personal. I've been trying to come up with a formula where we can put in numbers and it can spit out the answer, and I think for everyone it's different, we value different things and we have different situations, so I wasn't able to come up with a calculation for myself or to share with you all, but what I can share is a prompt to help you. What I did is I asked it to write a business plan based on the mission, and I pasted the mission for women in AI, and it was interesting to see what the AI spit out because it gave me a starting spot. I didn't have to deal with this blank page problem. Oh my gosh, how am I going to write this entire business plan? It can feel intimidating and it can feel scary, but it doesn't have to be so.

Speaker 2:

Any step you take is a step towards building your side hustle and deciding when the time is right to make a move. Growth is growth, no matter how I smell. I'm not sure who said this quote, but when you're in this phase, it might feel really hard to build a whole business or a whole agency or an entire company. When you don't look at it like that and you break it down into these smaller packages, it can feel a lot more manageable. So I encourage you to look at small, bite-sized pieces you can do every day. You can go to your nine to five and then come home and do something, or you can start the day with something for your side hustle and then hit up your nine to five. It's very important to celebrate the small wins always, but especially in the side hustle phase. So let's say you've been doing your side hustle and you're ready, you're excited and it's time to jump ship is actually doing some financial planning figuring out your burn rate, figuring out your risk management, figuring out your clients and then building a support system and seeking mentorship. You're in a great place here today with all of these amazing presenters who have different offerings and different support systems that they can provide you. So definitely reach out and continue to develop your new skills and expanding your network.

Speaker 2:

This will help For this section. The prompt is write a resignation letter for company name and address it to manager's name and cite that your last date will be insert date. It can do this. I actually had a friend who did this, so take some of the stress off of you and pass it over to the AI. A quote I wanted to leave you with I learned to always take on things I'd never done before. Growth and comfort do not coexist, and this is from Virginia Romney, the IBM CEO for many years, so keep that in mind as you're doing your calculations.

Speaker 2:

I wanted to share the metrics from the impressions for my LinkedIn for women in AI. You can guess when I jumped ship. Yeah, it's right here. When I had some time, I was able to skyrocket and be able to get more people involved in what I'm doing. We were able to go from not even having a website, just a logo, to having a podcast with 47 women waiting to come on as guests. So as soon as you have more time, that stuff you put in is the stuff you get out, so keep that in mind.

Speaker 2:

Lastly, a couple of key takeaways leverage AI for your side hustle. Manage it with your time and, when you jump ship, assess your goals and the market before you jump. All right, here's my contact info. You can scan the QR code. It'll go to my link tree. My gift today is our podcast. We talk a lot about AI and how you can use that to build a business and how other people are using it. So tune in anywhere you get your podcasts and please feel free to connect with me on LinkedIn and, of course, to follow Women in AI on LinkedIn. Are there any questions?

Speaker 1:

All right. Thank you so much, jenny, and, by the way, I'm gonna just as we're talking about the QR code, we have it up on screen. We were talking about this a little earlier. It used to be that you had to download software to scan a QR code and now you don't need to. So I'm going to keep this up as we see if there's any questions coming in from the audience. But I want to remind people if you want to download her resource, literally just pull out your camera on your phone right now. Hold it up as if you're taking a picture, try to get it fairly close to the QR code and then your phone will know there's a link there and then you can click on the link tree and then it opens it up from your phone. So the beauty of this technique is you can still be watching on your laptop and if there's any free resources that our speakers are sharing today, like Jenny is right now, I see LinkedIn, let's connect, I see free app monetization resources and I see her podcast, so I can go there right away without having to navigate out of my window. So really brilliant technique there, jenny, and so many great gems that you shared with us here today.

Speaker 1:

I want to see if there are any whoops. There's some comments coming in from folks like Laura and Meryl also saying, yes, always celebrate the small wins. Michelle, who's one of our panelists a little bit later, loves the quotes that you're having up on screen as well. And then we do have your LinkedIn. All the people are interested in finding you on LinkedIn, and I asked the question of you. I said do you go by Jenny K and or do you go by Jenny? Now, what's your preference? And tell us about that naming convention?

Speaker 2:

Yeah, so I actually go by Jenny when folks are talking to me but, believe it or not, there are actually a couple Jenny Pollocks, so I go by Jenny K Pollock when it's written out, so you know who you're actually talking to. I actually had a girl in the same major at college, at the same time as me, with the same name. It was very confusing, yeah okay, good to know.

Speaker 1:

So we go by Jenny, but her LinkedIn profile you'll find her at Jenny K Pollack, because there's other Jenny Pollacks that are out there. Jenny, thank you so much for joining. This is a great discussion. I want to thank you so much for coming out and joining us here. Thanks for having me.

People on this episode