3 entrepreneurs share tips

Living and working my passion

Want to turn your 5-to-9 into your 9-to-5? These firsthand tips from side hustlers-turned-small business owners can help you transform a passion project into a career.

Working for yourself can be hard work. But it may also bring you more joy and day-to-day satisfaction than your current full-time job.

According to one survey, half of millennials have a side hustle, and 53% of all people with side gigs depend on that income to make ends meet.Disclosure 1 But what if you want to build a career out of your side hustle? We spoke with three different entrepreneurs about the highs and lows of owning your own business, the importance of self-care, and advice they’d share with anyone looking to work for themselves.

You don’t always have to do it on your own

 
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Speaker 1 (00:00):

How many of us have thought, while working a nine-to-five job, I want to be my own boss.

Jeff (00:06):

Even though I enjoyed what I was doing, I didn't like having to work for someone else. That's a big reason why a lot of entrepreneurs end up getting started.

Speaker 1 (00:18):

That was Jeff Proctor, co-founder of DollarSprout.com, a personal finance education website.

Jeff (00:23):

We're helping people who are just starting to learn about money. We write about a lot of topics, such as saving money, making extra money, how to start investing for retirement. We're trying to be a good source for readers to learn about how to be a little bit smarter with their money. Most of what I focus on is managing our content team of writers, as well as working with different advertisers that we promote on our platform.

Speaker 1 (00:51):

Jeff started the company with his college friend, Ben Huber.

Ben (00:54):

I head off the social media marketing and like paid advertising analytics type stuff. So I kind of do the numbers and analytics portion of things, while Jeff kind of heads off more of the content creation.

Speaker 1 (01:05):

Jeff and Ben had always talked about eventually going into business together. But the path they took to starting a finance blog was a winding one.

Ben (01:12):

I went to school for biology. I ended up getting a degree in nursing.

Jeff (01:16):

So in college I actually studied biochemistry. I was wanting to go down towards the career path of something to do with medicine. And as time went on, I found that I really enjoyed reading and learning about personal finance, to where that was occupying all of my free time, rather than what I was supposed to be studying in school. After I graduated with my biochemistry degree in 2013, I was able to get a job working for a wealth management firm.

Speaker 1 (01:42):

Ben became a full-time nurse. While Jeff started working with high-net-worth clients.

Jeff (01:46):

I had liked working with people and helping people invest their money, but I really wanted to be able to help everyone, not just those with a high net worth. Even though I enjoyed what I was doing, I didn't like having to work for someone else. That's a big reason why a lot of entrepreneurs end up getting started, is they want to create their own thing and do things kind of your own way.

Speaker 1 (02:09):

The idea for DollarSprout.com and working for himself was planted. And Jeff began building up his savings. And he knew just who to turn to, to help him with the tech side of his startup.

Ben (02:19):

I had a background in technology, and I had run a hosting company during my years as a teenager. So I used my experience from that side hustle back then to help Jeff distribute his message of personal financing.

Speaker 1 (02:36):

Ben stayed in his nursing job, helping with the new business on the side until eventually deciding to join Jeff full-time. These two entrepreneurs are now enjoying the freedom and flexibility of being in charge. We talked with Jeff and Ben about the learning curve of starting a business and how they've managed the transition to being business owners. So Jeff and Ben, you both had a background in science and were working in pretty different fields from what your current business does. What was it like for you to make the leap? And what were some of the challenges that you ran into starting out?

Jeff (03:07):

The first entire year was just a massive learning curve. And when I look back on that experience, I really see that there was no shortcut for that. There was nothing I could have really done while working full time at my nine to five that would've truly prepared me for the learning that takes place, once you're fully on your own. As a result of that challenge, I started to deal with the stress of, you're not making enough money from the business to cover your personal bills. Your savings are running out. You'll tell yourself, "Okay, I've saved up a year's worth of money." And then when that sum actually starts to drop down, and then you've only got six months left of savings. And then three months left, two months left. It's quite a lot of stress.

Ben (03:51):

For me personally, working 50, 60 hours a week at the hospital, it didn't leave much time, literally in the day, to try to get things done. I was constantly trying to answer emails or work on a piece of content or trying to find a way to scale our marketing. And I think that that challenge is something that presents itself, is how do you balance good time management, devoting time to things that matter in your life and things that are mandatory. I think that it can get easy to get burned out, because sometimes you just kind of need to step back and think about how you can better prioritize your time.

Speaker 1 (04:23):

Did you guys experience that? What are some strategies you used to avoid feeling too burned out?

Jeff (04:27):

I'm always trying to keep a forward looking scope on where are we going to grow? Like where are we going to be three months from now, six months from now, a year from now? So being able to take that long-term perspective, also help mitigate some of that short-term burnout. But there's not really any way to actually totally negate burnout. But there might be a week or two weeks or a month or there might be a whole year where you're burnt out. But I think just keeping that long-term perspective is really important.

Ben (04:57):

Even if you get into business with the best of intentions, when you make that transition to a full-time job, it can seem like work. When I made the jump, it was actually a huge relief for me because I was balancing two jobs, so to speak. I was going from a 90-hour workweek down to a more manageable 40ish-hour work week. And even then, I got burned out. One of the things that we're really intentional about doing is taking time off together and then time off apart. We both enjoy golf, so sometimes we'll go play a round of golf just to kind of mentally reboot. And then other times we spend time apart. We completely unplug, no email, no laptop, nothing like that. And it kind of allows us to come back with a fresh mind. I think that people have the pressure of, when they're running their own business, they feel like they can't step away at all. They have to be hands on all the time. And even if you're running a one-man show, you have to be intentional about taking time off.

Speaker 1 (05:59):

So what has being a business owner meant for your financial confidence?

Ben (06:02):

So I know for me personally, financial confidence has really been improved because of what Jeff and I do in our business. When you run a business or you're fortunate enough to have a partner in your side hustle, there's a sense of accountability that may not be present when you are dealing with your own personal finances. You've got a second set of eyeballs, for better or for worse that are are kind of critiquing your decision-making. And that's translated really, really well for me personally, to my personal finances, just because I apply that same discipline to my personal spending. And I'm constantly thinking, is this something I need versus something that I want? And that has helped me start to really save for future goals. I know that Jeff and I are both actually pursuing home ownership here probably in the near future. And the discipline I've gained from the business is translating well into my saving for my home.

Jeff (06:52):

I started to look at my personal finances as just a smaller part of a bigger picture of like my total financial life. Which involves Ben, my business partner. But then it also will tangentially relate to Ben's family and my family. So I think that extra duty of obligation has really helped improve my own financial confidence and managing my own money and making sure that I'm able to meet my personal goals and have the business meet its goals.

Speaker 1 (07:24):

So what other advice would you give to someone thinking about turning their side project into a full-time business?

Jeff (07:28):

I think that a lot of it is risk management. You're going to have to take risk at some point, but I think that a lot of people probably make the jump too soon and I was one of them, and it cost me. So for instance, let's say you're making enough from your side gig to cover your personal bills and maybe even fuel a little bit of business growth. So that's great. But I like to think about, if you were to quit your job today and let's say part of your business income or your source of income dropped by 50% the next day. Are you going to be okay with an instant drop in income from something outside of your control?

Ben (08:06):

Part of it kind of depends on what exactly your side hustle is. You know, say you're a freelance photographer and you're deciding whether or not you want to leave your day job. You've already got several clients lined up. Your risk is not the same as someone who is jumping into an online business with no customer base. I think it's almost like a two-step process. You want to have realistic expectations for what sort of income you're going to generate if and when you do make the jump. And then have a budget in place.

Ben (08:33):

In my nursing field, I was making about the national average for a nurse of my tenure. And I waited to a point where not only we could support Jeff's living expenses, but we could maintain a standard of living that I was used to.

Jeff (08:45):

I think month one is great because you're excited to be an entrepreneur, you're all in, everything's great. And then month two through 12 were a little bit stressful because you know now there's actually pressure on you to pay your bills and grow your business. But then going from year two to three and beyond, now I'm getting to really enjoy the fruits of our labor, basically of working nonstop that first year or two. I probably work a little bit less now than I did back then. We're still enjoying the growth that we've been able to achieve and the benefits that come with that.

Speaker 1 (09:23):

Thanks again, Jeff and Ben.

 

Sometimes, your business may not take off on the first try. DollarSprout co-founders Jeff Proctor and Ben Huber found this out the hard way. After starting a wealth management firm and running out of money more quickly than planned, Proctor teamed up with Huber to create DollarSprout: a personal finance blog focused on helping its readers maximize their earning potential.

When they launched their new business, they quickly learned that the freedom and flexibility that came with being in charge has both pros and cons. There was a steep learning curve and some financial stress—but the two agree that having a business partner made things more manageable.

“My financial confidence has been improved because of what Jeff and I do in our business,” says Huber. “When you’re fortunate enough to have a partner in your side hustle, there’s a sense of accountability.”

Proctor and Huber have been able to apply the same discipline they have for their business expenses to their own personal spending—and were even able to save for homeownership because of it. But they caution not to jump into full-time business ownership too quickly.

“If you were to quit your job today, and your income drops 50% the next day, are you going to be okay with that?” asks Proctor.

Their other advice for building a career out of a side hustle?

  • Take time off for mental breaks.
  • Have realistic expectations for what kind of income you might make.
  • Start building your customer base before quitting your current job.
  • Create a budget—and stick to it.

Offer something that people really need or want

 
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Speaker 1 (00:00):

Aha that light bulb moment. The moment when you say, "Hey, this side project that I love working on in my spare time, what if I could find a way to make this my real job?"

Jason Patel (00:12):

Ultimately, what's so exciting is that when you can add value to someone's life, you're scaling that passion you have in your heart, and you're giving it to someone else. That's a really beautiful thing to have a positive impact on someone's life.

Speaker 1 (00:26):

That's Jason Patel, Founder of Transizion, a college admissions assistance and mentorship company.

Jason Patel (00:32):

We provide bootcamps and tutoring on college applications, AP exams, SAT testing, resumes and cover letters, and internship and job searches. Naturally, our audience includes freshmen through seniors in high school, and we strive to take the anxiety and stress out of the entire college admissions and application process for students and parents.

Speaker 1 (00:56):

Jason is just one example of an entrepreneur who was inspired to take a side project and turn it into a full-time job.

Jason Patel (01:02):

So I was a working college student, which meant that I had to work to pay my bills. And I applied for the job at our university's career center. I worked as a career mentor, helping college students and graduate students, and also visiting students with resumes and cover letters and helping them find internships and jobs once they graduated college.

Jason Patel (01:23):

After I graduated school, I worked in political communication because that was my major. And I also had a volunteering gig on the side where I helped young people navigate the college admissions process and find jobs and internships.

Speaker 1 (01:37):

Even though it was just an unpaid volunteer project, Jason could tell how invested he was in helping kids learn, grow, and meet their goals.

Jason Patel (01:44):

I fell in love with education. I loved growing young minds and helping young people find opportunities that could help them succeed in their careers in the short and long term.

Speaker 1 (01:55):

One of the students Jason worked with ended up being accepted into a top university. That student's mother suggested to Jason that he could turn this volunteer work into a business. Jason took the message to heart. He knew there'd be some risk, but he also knew he'd regret it later if he didn't at least give it a shot.

Jason Patel (02:11):

Opportunity is everywhere. If we can increase the productivity and happiness of our customers, we're doing better for our community. And the more we scale this, the more people we help, the more we're doing for the people around us and the communities that we want to get involved in. And think about it as if 50 years from now you had a dream that you didn't pursue, how would that make you feel? And I think ultimately what's so exciting is that when you can add value to someone's life, you're scaling that passion you have in your heart and you're giving it to someone else. That's a really beautiful thing to have a positive impact on someone's life, to be a part of someone else's journey, someone else's ambitions. It's a really great thing.

Speaker 1 (02:54):

Jason was able to turn his passion project into a full-fledged business, but what does that really look like? We talked with Jason about the day-to-day realities of being a small business owner and building confidence in the face of challenges.

Speaker 1 (03:08):

So Jason, I'm sure it was really exciting for you to bring your business idea to life, but I know it was a lot of hard work too. What did you find were some of the challenges of turning your side project into a business?

Jason Patel (03:19):

The first problem that I had was that originally I started Transizion because I wanted to give workshops, other career and college services to schools and organizations. But the thing is that many of these schools and orgs already have an in-house person to help them with these tasks and with these challenges.

Jason Patel (03:37):

I was marketing to an already saturated market. I didn't validate the idea going into it. I went in with rose-colored glasses with this idealism that if I went in with energy and great intentions, that people would automatically latch on to the idea and sign up and enroll, and therefore grow my business.

Jason Patel (03:55):

But I didn't validate it. You don't know what you don't know. And I didn't know that there will be so many unexpected costs. I had to budget and account for things a little better. So cash flow and time flow really was a challenge at first.

Speaker 1 (04:08):

So how did you overcome these challenges? What helped you work through them and build up your confidence?

Jason Patel (04:13):

My parents came to this country in 1985 without any money. And my mom worked in fast food, and my dad worked at a gas station and went to night school, and my mom supported him through night school. They struggled for a long time when they came here, like many immigrants struggled.

Jason Patel (04:30):

My dad eventually got a job at a computers company, and my mom got a job at an insurance company. They took their savings and they started a small business. What my parents have given me is this value of self-reflection and learning from failure and learning from the grind really.

Jason Patel (04:47):

They're very honest about their failures. They're very honest about how hard it is to balance individual finance with business finances. And they're very honest about how you should self-reflect and think about why you failed at something and then how to best iterate from there.

Speaker 1 (05:08):

So if you stop and think about it for yourself, what are some of the lessons that you learned? If you were going to give advice to someone who was thinking about starting this process, what would you want them to know based on your own experiences?

Jason Patel (05:20):

Don't simply quit your job or start that business, pour a bunch of money into it, and then realize your audience never existed, or the audience doesn't want to pay for it. And then of course the worst problem of all, your idea has no merit for product market fit. And therefore you spent time creating this idea of bringing it to life that no one wants.

Jason Patel (05:42):

The second thing I'd say is before you're quitting your job, take up all of your expenses, add them together, and multiply by two and a half or three. Because that's how much you'll be paying. Business is about pragmatism and making compromise.

Jason Patel (05:55):

We place a strong emphasis on encouraging the students to take a practical approach to their dream. You will have to compromise. You will have people who are too hard on you, or you will have people who don't appreciate what you do. You have to remind yourself why you're doing this, remind yourself why you're taking on challenges and doing things most other people don't do and most other people frankly, will think you're crazy for doing.

Speaker 1 (06:17):

So how do you do that? How do you give yourself those reminders about why you're doing this?

Jason Patel (06:22):

I think you have to learn how to balance business with life. When you do that on a day-to-day basis, you will gain confidence by it through discipline and repetition.

Jason Patel (06:31):

When you're operating a business, you're juggling personal expenses, business expenses, and probably more important, you're juggling your time. So many millennials and other people really ask that same question about finding their passion and then retaining that spark as the day-to-day grind hits you in the face and occasionally corrodes your enthusiasm for what you do.

Jason Patel (06:52):

Passion will keep you going at first, but it's not the thing that will sustain you over the course of six months to two years to six years to 10 years. Discipline's the thing that we'll do that.

Speaker 1 (07:05):

So what are some things that people can do to help achieve that balance. Is there anything that you do for yourself?

Jason Patel (07:11):

Read a lot of books. Do nighttime reading to help you relax and get your mind off the challenges that you encountered earlier in that day. Find a hobby. I know it's sort of a cliche for some entrepreneurs to say, I work a hundred hour weeks, 120 hour weeks. I have no time.

Jason Patel (07:28):

Having a hobby is really important because it takes your mind off the challenges you encountered early in the day. The same way books do that. My hobby is that I'm a jujutsu and Muay Thai competitor. Athletics gives me that chance to refine my competitive edge. It gives me a chance to iterate on something other than the business. It gives me a chance to meet people. It gives me a chance to make me a better person.

Jason Patel (07:53):

Always consider yourself a work in progress. You're always developing, and there's no limit. There's no ceiling for you to hit. You're always going to be better. There's always a new journey or a new challenge to take on.

Speaker 1 (08:04):

Great, thank you so much, Jason.

 

Transizion helps students and professionals alike advance their careers, whether it’s by guiding students through the college admissions process or coaching professionals interested in switching jobs. Jason Patel, Transizion’s founder, started it after he helped a student get into a top college and the student’s mother encouraged him to turn his tutoring side gig into a business.

“Opportunity’s everywhere,” says Patel. His motivation lies in helping people achieve their ambitions and bettering the communities he serves. He also credits his parents, who immigrated to America in 1985, for instilling lessons that he carries with him today.

“What my parents have given me is this value of self-reflection, learning from failure, and learning from the grind,” he says.

While getting the business off the ground was tough—Patel was entering an already saturated market and had to deal with many unexpected costs—he overcame those challenges by budgeting his money and time and learning to find balance in business and life. “When you do that on a daily basis, you’ll gain confidence through discipline and repetition,” he says.

Patel’s top tip for people building a business out of a side hustle is to not quit your full-time job and put everything into something nobody wants or needs. He also recommends:

  • Do your research before diving in.
  • Plan to spend 2.5 – 3 times more money than you expect.
  • Be realistic and willing to compromise.
  • Find a hobby to relax.

“Passion will get you going at first, but it’s not the thing that will sustain you over time. Discipline’s the thing that will do that,” Patel adds.

Confidence and knowing your value can help you succeed

 
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Speaker 1 (00:00):

How many of us have thought, while working a nine-to-five job, I want to be my own boss.

Jeff (00:06):

Even though I enjoyed what I was doing, I didn't like having to work for someone else. That's a big reason why a lot of entrepreneurs end up getting started.

Speaker 1 (00:18):

That was Jeff Proctor, co-founder of DollarSprout.com, a personal finance education website.

Jeff (00:23):

We're helping people who are just starting to learn about money. We write about a lot of topics, such as saving money, making extra money, how to start investing for retirement. We're trying to be a good source for readers to learn about how to be a little bit smarter with their money. Most of what I focus on is managing our content team of writers, as well as working with different advertisers that we promote on our platform.

Speaker 1 (00:51):

Jeff started the company with his college friend, Ben Huber.

Ben (00:54):

I head off the social media marketing and like paid advertising analytics type stuff. So I kind of do the numbers and analytics portion of things, while Jeff kind of heads off more of the content creation.

Speaker 1 (01:05):

Jeff and Ben had always talked about eventually going into business together. But the path they took to starting a finance blog was a winding one.

Ben (01:12):

I went to school for biology. I ended up getting a degree in nursing.

Jeff (01:16):

So in college I actually studied biochemistry. I was wanting to go down towards the career path of something to do with medicine. And as time went on, I found that I really enjoyed reading and learning about personal finance, to where that was occupying all of my free time, rather than what I was supposed to be studying in school. After I graduated with my biochemistry degree in 2013, I was able to get a job working for a wealth management firm.

Speaker 1 (01:42):

Ben became a full-time nurse. While Jeff started working with high-net-worth clients.

Jeff (01:46):

I had liked working with people and helping people invest their money, but I really wanted to be able to help everyone, not just those with a high net worth. Even though I enjoyed what I was doing, I didn't like having to work for someone else. That's a big reason why a lot of entrepreneurs end up getting started, is they want to create their own thing and do things kind of your own way.

Speaker 1 (02:09):

The idea for DollarSprout.com and working for himself was planted. And Jeff began building up his savings. And he knew just who to turn to, to help him with the tech side of his startup.

Ben (02:19):

I had a background in technology, and I had run a hosting company during my years as a teenager. So I used my experience from that side hustle back then to help Jeff distribute his message of personal financing.

Speaker 1 (02:36):

Ben stayed in his nursing job, helping with the new business on the side until eventually deciding to join Jeff full-time. These two entrepreneurs are now enjoying the freedom and flexibility of being in charge. We talked with Jeff and Ben about the learning curve of starting a business and how they've managed the transition to being business owners. So Jeff and Ben, you both had a background in science and were working in pretty different fields from what your current business does. What was it like for you to make the leap? And what were some of the challenges that you ran into starting out?

Jeff (03:07):

The first entire year was just a massive learning curve. And when I look back on that experience, I really see that there was no shortcut for that. There was nothing I could have really done while working full time at my nine to five that would've truly prepared me for the learning that takes place, once you're fully on your own. As a result of that challenge, I started to deal with the stress of, you're not making enough money from the business to cover your personal bills. Your savings are running out. You'll tell yourself, "Okay, I've saved up a year's worth of money." And then when that sum actually starts to drop down, and then you've only got six months left of savings. And then three months left, two months left. It's quite a lot of stress.

Ben (03:51):

For me personally, working 50, 60 hours a week at the hospital, it didn't leave much time, literally in the day, to try to get things done. I was constantly trying to answer emails or work on a piece of content or trying to find a way to scale our marketing. And I think that that challenge is something that presents itself, is how do you balance good time management, devoting time to things that matter in your life and things that are mandatory. I think that it can get easy to get burned out, because sometimes you just kind of need to step back and think about how you can better prioritize your time.

Speaker 1 (04:23):

Did you guys experience that? What are some strategies you used to avoid feeling too burned out?

Jeff (04:27):

I'm always trying to keep a forward looking scope on where are we going to grow? Like where are we going to be three months from now, six months from now, a year from now? So being able to take that long-term perspective, also help mitigate some of that short-term burnout. But there's not really any way to actually totally negate burnout. But there might be a week or two weeks or a month or there might be a whole year where you're burnt out. But I think just keeping that long-term perspective is really important.

Ben (04:57):

Even if you get into business with the best of intentions, when you make that transition to a full-time job, it can seem like work. When I made the jump, it was actually a huge relief for me because I was balancing two jobs, so to speak. I was going from a 90-hour workweek down to a more manageable 40ish-hour work week. And even then, I got burned out. One of the things that we're really intentional about doing is taking time off together and then time off apart. We both enjoy golf, so sometimes we'll go play a round of golf just to kind of mentally reboot. And then other times we spend time apart. We completely unplug, no email, no laptop, nothing like that. And it kind of allows us to come back with a fresh mind. I think that people have the pressure of, when they're running their own business, they feel like they can't step away at all. They have to be hands on all the time. And even if you're running a one-man show, you have to be intentional about taking time off.

Speaker 1 (05:59):

So what has being a business owner meant for your financial confidence?

Ben (06:02):

So I know for me personally, financial confidence has really been improved because of what Jeff and I do in our business. When you run a business or you're fortunate enough to have a partner in your side hustle, there's a sense of accountability that may not be present when you are dealing with your own personal finances. You've got a second set of eyeballs, for better or for worse that are are kind of critiquing your decision-making. And that's translated really, really well for me personally, to my personal finances, just because I apply that same discipline to my personal spending. And I'm constantly thinking, is this something I need versus something that I want? And that has helped me start to really save for future goals. I know that Jeff and I are both actually pursuing home ownership here probably in the near future. And the discipline I've gained from the business is translating well into my saving for my home.

Jeff (06:52):

I started to look at my personal finances as just a smaller part of a bigger picture of like my total financial life. Which involves Ben, my business partner. But then it also will tangentially relate to Ben's family and my family. So I think that extra duty of obligation has really helped improve my own financial confidence and managing my own money and making sure that I'm able to meet my personal goals and have the business meet its goals.

Speaker 1 (07:24):

So what other advice would you give to someone thinking about turning their side project into a full-time business?

Jeff (07:28):

I think that a lot of it is risk management. You're going to have to take risk at some point, but I think that a lot of people probably make the jump too soon and I was one of them, and it cost me. So for instance, let's say you're making enough from your side gig to cover your personal bills and maybe even fuel a little bit of business growth. So that's great. But I like to think about, if you were to quit your job today and let's say part of your business income or your source of income dropped by 50% the next day. Are you going to be okay with an instant drop in income from something outside of your control?

Ben (08:06):

Part of it kind of depends on what exactly your side hustle is. You know, say you're a freelance photographer and you're deciding whether or not you want to leave your day job. You've already got several clients lined up. Your risk is not the same as someone who is jumping into an online business with no customer base. I think it's almost like a two-step process. You want to have realistic expectations for what sort of income you're going to generate if and when you do make the jump. And then have a budget in place.

Ben (08:33):

In my nursing field, I was making about the national average for a nurse of my tenure. And I waited to a point where not only we could support Jeff's living expenses, but we could maintain a standard of living that I was used to.

Jeff (08:45):

I think month one is great because you're excited to be an entrepreneur, you're all in, everything's great. And then month two through 12 were a little bit stressful because you know now there's actually pressure on you to pay your bills and grow your business. But then going from year two to three and beyond, now I'm getting to really enjoy the fruits of our labor, basically of working nonstop that first year or two. I probably work a little bit less now than I did back then. We're still enjoying the growth that we've been able to achieve and the benefits that come with that.

Speaker 1 (09:23):

Thanks again, Jeff and Ben.

 

Speaker 1 (00:00):

Confidence, flexibility, creativity, an open mind. These are all traits that help you succeed in business, or on an improv stage.

Jen Brown (00:11):

You don't plan too far ahead. You don't look too far back. You respond to what's happening right in front of you. That's what gets you through a lot of those challenges in the beginning and in the two-year, three-year, four-year, 10-year, 20-year mark of business.

Speaker 1 (00:31):

That's Jen Brown, founder of The Engaging Educator, a company that uses improv comedy techniques to help people, especially women, become better speakers and communicators.

Jen Brown (00:40):

We work with either individuals or with organizations, and we're teaching them public speaking skills, communication skills, all through improv-based education. A lot of the stuff we work on is networking and small talk, also presentations, pitching the clients, even just working up confidence to be able to speak up at work. So we're using this very lighthearted way of examining these really deep things with communication.

Speaker 1 (01:08):

For Jen, improv was a fun activity she did during the evening. Her day job was something quite different.

Jen Brown (01:14):

By day, I was working as a museum educator, as the person that walked around with school groups, gave them tours, gave them information, things like that. Improv by nights, museum educator by day.

Speaker 1 (01:27):

As it turned out, improv was a natural fit for her museum job.

Jen Brown (01:30):

Improv at its core is just really listening and responding. I could pay attention. I could be in the moment. I could listen. My boss called me her show pony. And that meant that she could put anyone on my tour and I wouldn't get rattled because I had done such ridiculous things in improv that I don't think I cared who was on my tour, I knew how to focus.

Speaker 1 (01:51):

Jen realized how much she was benefiting from improv and that it could help other people too. She also realized that she loved teaching improv more than performing. So she planned a workshop on improv and communication and it sold out. As her side hustle began to take over her life, Jen realized that it was now or never to turn this hobby into something more.

Jen Brown (02:09):

I realized that the only way that I could do this in a way that it would be taken seriously as a business was if I committed myself to it. I had to stop the, "Okay, I'm doing this on the side. I'm doing this on the side," because it diluted my personal life and my just health and wellness that I was working essentially two full-time jobs and sleeping as much as you could imagine when you're working 80 hours a week.

Speaker 1 (02:38):

Being able to pivot on a dime used to be something that Jen did just for fun. But now it's her full-time job. We sat down with Jen to hear more about her journey. So Jen, your business is all about teaching confidence to other people. But how did you find your own confidence when you were just starting out?

Jen Brown (02:56):

I think that was the biggest challenge in the beginning, not just for myself, to take myself seriously, for other people to take me seriously. And I do look back now and I hear myself talking about the business and I'm like, "No wonder I struggled in the beginning being taken seriously," because I was apologizing for myself constantly. You have to trust yourself, because if you're not believing in yourself, no clients will believe in you. No customers will pay you to do what you do.

Jen Brown (03:25):

As someone who came from a theater background and a dance background and an art history background, all things I had degrees in, I never businessed. So I didn't know what it was like. It was a big learning curve for me. You have to be able to pivot and kind of be in the moment. And I think that's why my improv background is so helpful because I respond to what's happening around me. You don't plan too far ahead. You don't look too far back. You respond to what's happening right in front of you. And when you do that, then you'll succeed because you roll with it, you move around, you do what you got to do. And that part of that flexibility, that's what gets you through a lot of those challenges in the beginning and in the two-year, three-year, four-year, 10-year, 20-year mark of business.

Speaker 1 (04:21):

What are some other lessons you've learned from being a business owner?

Jen Brown (04:24):

It has made me so hyperaware of spending and how time is money and where my money goes. I pay attention to do I really need this $5 coffee? Or should I save this $5 coffee and hire a branding firm down the line? And that's not saying I don't still treat myself. When you run a business, if you put work into it and you are constantly learning and striving to be better and faster and stronger, you get that out of it. And that is directly correlated with my financial confidence. Because if I'm putting money into my business, I know that it's going to pay off in the end.

Speaker 1 (05:17):

How do you find the energy for the day to day responsibilities that come with running your own business?

Jen Brown (05:21):

If I'm having a difficult day, I'm like, "All right, you know what? I can get this, this, and this done and then I'm going to walk away and start fresh tomorrow." Or, "I'm going to do this one thing that I know I really love doing that needs to be done still, and then tomorrow I'm going to do the harder thing or the thing that I'm struggling with."

Jen Brown (05:41):

I think that the biggest thing is take some time to step back and look at the full picture. I was going day to day so much in the beginning. And when I hit year five, I was like, "I don't want to go day to day anymore. I want to know what my year goals are, or two-year goals or three-year goals." That up and down is what running your own business is all about. It's the highs and the lows. It's not going to be sunshine and rainbows just because you work for yourself. Are the highs worth the lows? Are the lows too low that the highs don't make up for it? Because as much as we want to say we're doing it because we love it and the good of our heart, bills got to be paid. So how are you going to get people to pay you for what you do or what you create? And if you can answer that question, if you know your value, then you should go for it if you want to. If you don't, then keep it as a hobby, keep it as a side hustle because it will no longer feel a hobby once you start doing it for work.

Speaker 1 (06:51):

So what can people do to figure out if something should just stay a hobby or if it can turn into a business opportunity?

Jen Brown (06:57):

I think the thing that I always tell new entrepreneurs is, "How can you do this and still love what you're doing?" Because sometimes that hobby is your hobby because it takes care of you. I absolutely love crafting. I would never start a business in it because that is something that I do for self-care. I can say, "All right, well I'm going to sit here and crochet something." And people have said in the past, "Oh, why don't you make blankets and sell blankets?" And I'm like, "That would take the fun out of it for me." And I think that so many people confuse a hobby that they really love doing with something that could be a potential business for them. Because when you are starting a business, it becomes work.

Speaker 1 (07:44):

Did you have that experience with improv?

Jen Brown (07:47):

So, improv for me is work now. It means everything to me when I can get into a room, work with a group. I have so much fun. I do love it. It is a passion of mine. It is still work. I don't perform anymore. I have no interest in that. I don't go see improv shows anymore. No interest in that. I spend my free time taking care of myself, cooking with my family. My husband and I, we cook all the time. I taught him how to crochet. You have to take care of that passion, because even if it becomes work, you still have to love it and enjoy it. You still have to feel something for it. So making sure that you're taking care of yourself while you're taking care of your business, I think, and not just going all in because you're excited is a really, really important advice point.

Speaker 1 (08:40):

Awesome. Thanks again, Jen.

 

Improving communication through improv is what Jen Brown is all about. She uses improv comedy techniques to help people—especially women—become better speakers. As a performer, she realized that improv teaches skills people need for life: staying present, responding to what’s right in front of you, and being flexible to overcome challenges. That’s why she decided to start The Engaging Educator.

At first, she kept her teaching as a side hustle while working a full-time job. But eventually it became too much—Brown says working two jobs was “diluting her personal life and health.” So, she decided to commit to teaching improv full-time and hasn’t looked back.

“I was apologizing for myself constantly,” Brown says. “You have to trust yourself, because if you’re not believing in yourself, no clients will believe in you.”

Brown says she’s learned many lessons from being an entrepreneur, like:

  • Be “hyper-aware” of spending and where your money—and time—goes.
  • You have to make personal money sacrifices to benefit your business.
  • Take time regularly to step back and look at the full picture.
  • Confidence can help you get out what you put into your business.

Like many other entrepreneurs, Brown emphasizes the importance of taking time for yourself. Refreshing your mind is incredibly important, especially when an activity you love becomes your full-time job—your once-hobby will feel like work.

“As much as we want to say we’re doing it because we love it, bills have to be paid,” Brown says. “How are you going to get people to pay you for what you do or create? If you can answer that question and know your value, then you should go for it. If you can’t, then keep it as a hobby or a side hustle.”

The advice from all of these entrepreneurs on building a career out of a side hustle follows similar themes: don’t dive in too quickly, learn to manage your time and expenses, and schedule time for yourself. Learning these lessons can help you succeed when attempting to turn your passion into sustainable income. 

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