161. Plan Your Leap from Corporate to Solopreneurship the Smart Way - A Sound Bite Episode

Are you ready to break free from the 9-to-5 grind and turn your passion into your livelihood? In this sound bite episode of The Aspiring Solopreneur, hosts Carly Ries and Joe Rando dive into the exciting—and sometimes daunting—journey of solopreneurship. They share their own cautionary tales, practical tips, and cheerleading moments to inspire you to make the leap with confidence.

From planning your transition while still employed to nailing down a lead generation strategy and understanding the hidden challenges of going solo, Carly and Joe offer a roadmap to success. 

Whether you’re considering a side hustle or ready to dive in full-time, this episode is packed with actionable advice to help you build a thriving solopreneur business—without the feast-or-famine cycle.

Tune in to learn why preparation is your best friend and how to create a sustainable, fulfilling business on your terms. Don't miss this empowering conversation designed to help you take control of your career!

Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr's SoloSuite Intro gives you free education, community, and tools to build a thriving one-person business.  So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, be sure to check out LifeStarr Intro!

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What is The Aspiring Solopreneur?

*Formerly known as Solopreneur: The One-Person Business Podcast*

Welcome to The Aspiring Solopreneur, the weekly podcast that dives deep into the world of solopreneurship. Join us as we bring you insightful interviews with industry experts and successful solopreneurs who have mastered the art of running their own businesses.

Are you a solopreneur looking for guidance on how to attract clients? Or maybe you're searching for ways to stay motivated and overcome the challenges of working alone. Perhaps you're even struggling with the intricacies of taxes and financial management. No matter what obstacles you face, The Aspiring Solopreneur Podcast is here to provide you with the knowledge, inspiration, and practical advice you need.

In each episode, our hosts, Joe Rando and Carly Ries, sit down with a diverse range of guests, including seasoned solopreneurs, marketing gurus, financial experts, and productivity specialists. Together, they unpack the secrets to solo success, sharing their personal stories, strategies, and actionable tips.

Learn from those who have paved the way before you, as they reveal their tried-and-true methods for growing their company of one.

Subscribe now and join our community of solopreneurs who are committed to achieving their goals, mastering their craft, and creating a fulfilling and prosperous business on their own terms. Get ready to unlock the secrets to solo success and become the best version of yourself as a one-person business owner.

Want to learn from and grow with other solopreneurs? Join our movement for FREE at https://www.lifestarr.com/solosuite-intro-for-solopreneurs

Carly Ries: 00:00

Today, we're diving into one of the most significant and exciting shifts you can make in your career, transitioning from corporate to the world of solopreneurship. Have you ever sat in a corporate meeting and thought there's gotta be more than this? Maybe you've dreamed of being your own boss, working on projects that truly light you up, and building a life with more freedom, flexibility, and fulfillment. Well, you're not alone. And in this short episode, we explore what it takes to take that leap, avoid common pitfalls, and set yourself up for success.

Carly Ries: 00:29

So whether you're just beginning to consider solopreneurship or you're already on your way, this episode is packed with real talk to help you navigate this solo journey. You're listening to The Aspiring Solopreneur, the podcast for those just taking the bold step or even just thinking about taking that step into the world of solo entrepreneurship. My name is Carly Ries, and my co host Joe Rando and I are your guides to navigating this crazy, but awesome journey as a company of 1. We take pride in being part of LifeStarr, a digital hub dedicated to all aspects of solopreneurship that has empowered and educated countless solopreneurs looking to build a business that resonates with their life's ambitions. We help people work to live, not live to work.

Carly Ries: 01:13

And if you're looking for a get rich quick scheme, this is not the show for you. So if you're eager to gain valuable insights from industry experts on running a business the right way the first time around, or want to learn from the missteps of solopreneurs who've paved the way before you, then stick around. We've got your back because flying solo in business doesn't mean you're alone. So, Joe, this is our first sound bite recording after the new year, and I feel like a lot of people are like, you know, this is the year I'm going to follow my passion. This is the year not gonna just, deal with the status quo.

Carly Ries: 01:48

I'm gonna actually do what I wanna do, and it can be hard. And people are trying to take that or a lot of people are thinking about taking that leap from corporate to solopreneurship. It's just a growing trend, and I kind of feel like we should talk about our stories, kind of our cautionary tales, but also our cheerleader tales and, just really motivate people to follow what they wanna do and enter the world of solopreneurship. What do you think?

Joe Rando: 02:14

Well, I think so. And I think every time I see one of these back to the office mandates from some Fortune 500 company, a lot more people start thinking about what it would be like to be a solopreneur.

Carly Ries: 02:25

Yeah. Oh, absolutely.

Joe Rando: 02:26

Thank you, Fortune 500.

Carly Ries: 02:27

Yes. Exactly. Well, I jumped into the world of solopreneurship back in 2016, and I remember being terrified because I am a very social person. I'm very extroverted, and I was nervous I was going to lose that when I left into solopreneurship. Turns out I'm much more engaged now as a solopreneur than I was before, and that was one of my biggest years.

Carly Ries: 02:53

But looking back even more now, like that's someone that stands out. But just thinking of the things that I wanted to get in place before I jump ship and what I recommend to other people is having an idea of what you wanna do. We have the success cycle, and we talk about icky guy and figuring out your business. A lot of this stuff should really be done before you jump ship from the corporate world. I feel like the planning part of your business should be done while you still have a job so that your execution phase can be done when you leave. Do you agree?

Joe Rando: 03:27

Absolute I mean, there is no reason not to plan your business while you're still working unless you work 20 hours a day, 7 days a week. I mean, the planning stuff can be done at any time. You can do it at night, you can do it in the morning over coffee. But all that stuff is so important to get right and so important to to check before you leap. So I absolutely suggest going through first phase, that envision phase, right?

Joe Rando: 03:55

Where you with your goals, what do you want out of this, why are you doing this? Because it ain't gonna be easy. And as easy as you think it's gonna be, you know, my favorite little meme there, we do this not because it is easy, but because we thought it would be easy. And so true. So just remember that you gotta have a good reason for doing it, get those goals written down, those whys written down, and then imagine the business.

Joe Rando: 04:20

Start with imagining it and check if the business makes sense, talk to people. You can do all this stuff, if you keep it discreet while you still have a job and get some feedback and develop a good idea that you can then start with. And then when you leave or maybe not leave, maybe you just do a side hustle for start. I mean, that's a really good way to kind of keep that income and benefits going and get your business to the point where it's grown enough that you can make that leap without having to go on to you know, benefits from the government to buy your groceries. So, I think it's a really good idea to start with a side hustle unless you've got something that you can really leap into regard to business, I'm saying, you know, if you can line up a bunch of clients before you even leave your company, great.

Joe Rando: 05:07

Go for it. But if not, you know, take your time. Do it slowly.

Carly Ries: 05:12

I'm so glad you said line up your clients because the biggest thing, I would argue the biggest thing we hear from solopreneurs is their issue with lead generation and getting those clients. Their business is great. They tested it with people, and everybody said, yeah. This is a really good idea. And so they think that means it's time to jump ship, but you need to have a lead gen strategy in mind and tested before you leave.

Carly Ries: 05:37

And you also need to figure out how that pipeline is going to continue. We talked about recurring revenue last week, and you just need to make sure that you're not solely relying on the one client you get and just focusing all the time and attention towards them once you leave corporate. You need to have that client, and then you need to continue working on getting your next client because you never know when that first client's going to leave. So just to save you the stress, really think about your lead gen strategy before you leave corporate, because that's essential for the livelihood of your business.

Joe Rando: 06:13

You know, it's the same pattern we see over and over. People, they leave. They start their solo business. They know a bunch of people. They have a network.

Joe Rando: 06:22

They engage some of those people as clients. Everything's wonderful. And then, you know, some time goes by and they start leaving because either they're finished or whatever, and the pipeline is empty. And it's like, oh, no. What do I do now?

Joe Rando: 06:34

And you end up with that feast or famine, then they're off, you know, building up the leads. And so you need that process like you're saying. And just to put some color on what you're saying too with the couple of clients. I started a company. It wasn't a solopreneur company.

Joe Rando: 06:48

It was with a partner. And for a number of years, we had 2 customers. They were great customers and they were paying a good amount of money and it was making us profitable, but there were 2. And if one of them left, we were doomed. And it was a very uncomfortable place to be. we eventually got focused, got that up to 75 or 80 customers. And then it was a lot less scary when the prospect of somebody leaving for whatever reason came along because it was, not gonna be half the business.

Carly Ries: 07:20

Yeah. And, Joe, the other things I would consider so lead gen is 1, but, also, think about the things that you don't realize other people were doing for you in the corporate world that you now need to do for yourself. So for me, taxes was like I mean, when you're working for a company, your taxes are, much easier than when you're a solopreneur.

Joe Rando: 07:42

Just put that W2 in.

Carly Ries: 07:44

Exactly. So figuring that out, health insurance, most companies provide health insurance. You need to figure that out. Joe, we were talking offline about COBRA and being able to extend your coverage. I think that is a great option for people, but I would also say shop around because COBRA can be really expensive.

Joe Rando: 08:01

Yeah. It can. You're basically paying what the company's paying and sometimes, I mean, sometimes it's really great coverage and it's worth keeping and sometimes it's just better for you to find something maybe a little less robust and, a lot less expensive.

Carly Ries: 08:14

Yeah. But the other things I would say in terms of thinking what other people would do for you, just as an example, I'm in marketing, but when I was working for an agency, I was often client side doing strategy, Client interactions. I was the liaison between the client and the rest of the agency And I'm not great at ppc and I'm not great at social because I always allocated that or delegated that to other teams within the agency. I was like, okay. So I know I need to outsource these things or learn these things if time allows. so think about those skills that you've always been able to offer in your corporate world that you may not wanna focus on in your entrepreneurial world and think of how you can still either drop those, delegate those, or educate yourself on those before you leave, and see if you still wanna offer what you're used to offering as a corporate job.

Joe Rando: 09:09

Yeah. absolutely great advice. Hey. just one thing I wanna back up on COBRA.

Joe Rando: 09:14

I'd meant to mention, if your company has fewer than 20 employees, in some places, you may not qualify for COBRA. So don't assume it. do your homework. I just wanna put that out there because I'd hate to have somebody find out the hard way.

Carly Ries: 09:29

So moral of the story, we are big champions for

Carly Ries: 09:31

solopreneurship, obviously. That's what LifeStarr is all about, but don't jump into it blindly. Ask yourself if you think you can even be a solopreneur. Some people, are not cut out for it. We're actually developing a quiz right now to see if people are actually ready for going out in the solo world.

Carly Ries: 09:50

But just ask yourself, am I self motivated? Is this something I actually wanna do? Or if you're just frustrated with your job, you will get impostor syndrome. That's a given. Just prepare for that.

Joe Rando: 10:00

It's a good thing. It's a good thing. think impostor syndrome is good, it means you know what you don't know, which people when they get started don't have that. Right? They don't even know what they don't know, and they're like, oh, will be easy.

Carly Ries: 10:14

Exactly. So we say go for it. If solopreneurship is in your cards, 100% behind you, and we're happy to help with every step of the way. But just get your ducks in a row before you jump in, and, that's my advice.

Joe Rando: 10:26

I think it's great advice. Thanks, Carly.

Carly Ries: 10:29

Well, thanks for tuning in, listeners. As always, we'd love that 5 star review. Please subscribe on any of your favorite podcast platforms, including YouTube, and we will see you next time on The Aspiring Solopreneur.

Closing: 10:42

You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.