Should You Actually Start a Side Hustle w/ Stef Caldwell

UX Marketing

Blake: [00:00:00] today on the podcast you have Stef Caldwell, who is going to tackle a bunch of different subjects with us. Today we're going to be discussing things like side hustles and authenticity and customer experience, kind of the, the whole gamut.

[00:00:11] But I'm really excited about this one. But Stef, before we get into it, I do want to give you a chance to give some context about yourself. Basically, if you could just tell us, first and foremost what your career path has been to this point, where you got started and how you got to where you are now.

[00:00:28] Stef: [00:00:28] Happy to do that and thanks for having me on the show. So my career path, if you just looked at it on LinkedIn, might be confusing to somebody who doesn't know kind of where I'm headed. So I started, , my first internship was in recruiting, right? I worked at a staffing firm where I was recruiting people and, and helping place them in jobs.

[00:00:48] In my professional career, I moved from being a business analyst to working in a sales and marketing role, to then working in a product management role and a channel development role to now where I sit, which is in customer success. And so again, , any person would look at that experience and be like, huh, this girl's really, , been all over the place in terms of her variances.

[00:01:08] But the way that I look at it is I'm collecting the experiences necessary to make me the most ultimate general manager or CEO of a business. And I think that, okay, really, really incredible leaders can empathize with their people in any department. And so I really navigated my career path. Bye bye.

[00:01:28] Creating opportunities to have those experiences so that when I do become, you're the leader and I am, , and my side hustle that I can really emphasize and create good experiences across departments.

[00:01:39] Blake: [00:01:39] Oh, that's a, that's a pretty unique. Viewpoint, I guess because most people when they go into a side hustle are basically just looking to make money.

[00:01:47] That's, I mean, that's the facts of the matter, and I love that you're really more like people focus your people customer centric. That's going to bode really well for you down the road, and it's gonna be great for our audience as well, because I think it's a really important message to hear. And before we dive too much more in detail, I do ask everybody, what do you consider to be your professional superpower?

[00:02:13] Stef: [00:02:13] I think adaptability and tenacity. So whatever the baby is, of those two words, that's me.

[00:02:20] Blake: [00:02:20] It's a necessity.

[00:02:21] Stef: [00:02:21] Untapped tenacity. Yes. it's, . I believe and truly like live out every day that everything is figureoutable and having that mentality and then also having the willingness to get up everyday and take one step forward, even if that step is very uncertain, I think is what sets me apart in my professional career as well as in my side hustle.

[00:02:44] Awesome.

[00:02:44] Blake: [00:02:44] Well. I know that you do work full time at narrative science. Correct. So you've, you've already got the full time job. Now you also have the side hustle thing going on. obviously the word side hustle itself is self explanatory. Do you understand that it's something you're doing on the side? You already have a full time job, but it's another thing to actually help people understand how you can do that.

[00:03:06] And so you're in a unique position where you can discuss that a little bit with us. I'm curious right now, what does your day to day look like? I mean that, that may be a bad question because right now we're going through all this coronavirus stuff and everybody's normal is completely out of whack, but normally how are you balancing having a full time job that's, that's demanding where you're trying to learn skills and grow and you're doing a side hustle at the same time.

[00:03:31] Stef: [00:03:31] That's a really good question. And because my side hustle is helping women optimize their lives and kind of step into the woman they were born to be. I talk about this often. It starts with boundaries. I am ruthless about my boundaries and I know specifically what my dream day looks like, which starts with know.

[00:03:50] Putting my physical and mental health first through practices like yoga and journaling and meditation and making sure that I set myself up for a successful day because my days are strenuous. Then, , I go directly from kind of my self care routines into working at narrative science where. , my, my day really changes.

[00:04:10] I'm in customer success. So it depends on, , what the customer problem is or what the, the advices that I'm giving to any other department to ensure that our customers have a great experience. And then my day kind of ends, , between five and six o'clock when I transitioned over to working for manifests full time.

[00:04:28] And I think it's an important distinction. A lot of side hustlers, they're like, Oh, it's, , it's my side hustle. To me manifest is, is something that I would love one day to be the hustle, right? And so the way that I am orchestrating, , my team and orchestrating our client experiences is such that, , we're setting ourselves up for a broader future.

[00:04:47] So. I tell my husband all the time I worked, I worked two full time jobs. It's just that the hours are distributed differently. If you look day to day, Saturday and Sunday, full time manifest Monday through Friday, full time narrative science. So it's a, it's a lot of effort. It's a lot of work. Okay. I'm doing it because all of these things bring me joy.

[00:05:10] So it's a choice and I choose kind of every day too, spend the time doing those things. I have

[00:05:16] Blake: [00:05:16] many questions following up on that, but I'll start with from the company's viewpoint, because there are a lot of companies out there that are at their very roots, very entrepreneurial, so they're okay with people having side hustles.

[00:05:27] They understand it. Then there are a lot of traditional businesses, probably the majority of businesses that actually look at that and say, why aren't you giving us a hundred percent of your time? So how, how do you go about, if you were in that position of working for a traditional company, like many of our audience is going to be right now, but you want to do a side hustle, how might you convince your employer or your company that it's actually a good thing for you to have your own little side project?

[00:05:53] Stef: [00:05:53] So it manifests, we talk about the people in our lives as, expanders, people that are the validation that you need to prove that that success that you're seeking as possible for you. I think when I started with manifest, I wasn't sure how to communicate this idea to my company that I was going to be doing something on the side.

[00:06:14] And , when I first started, it was small enough that it was just a few hours a week where I was planning events to bring women in Chicago together, that it was really manageable. And now it's become a little bit more of who I am, obviously. And so. To answer your question, I think it's find someone who can be an expander for you.

[00:06:35] What I found the second I started my side hustle, it was that was actually more effective and an even better employee of narrative science because I was thinking like a business owner and it narrative science. That's something that they really value in the respect they say, I mean, we are all owners of narrative science in a sense because we have equity positions in the company.

[00:06:55] But it's difficult when you're working for someone to really feel that ownership. And when I started working at manifest and every dollar that was going out the door was mine, and I was, , mobilizing a team in all these directions, achieve these outcomes. I started applying all of that in narrative science.

[00:07:12] So neuroscience science isn't getting, , two years ago, Stefanie, pre side hustle, value anymore. They're getting full blown, like super power value out of me because I've got these two lives and they're teaching me and informing one another. So find an expander who is the validation you need, understand their story, and then communicate that to.

[00:07:33] Your company so that you can help them realize that you're not going to be splitting your time. You're actually going to be even more effective in all the time that you spend, regardless of where you're spending that time.

[00:07:42] Blake: [00:07:42] I love that. I've never heard the concept of an expander, so kudos to you. That's, that's awesome.

[00:07:47] Stef: [00:07:47] But even Aboriginal work, that's fine.

[00:07:52] Blake: [00:07:52] And expanding even further though. You're probably a proponent of everybody having a side hustle. Right? But I'm curious, if I were to play devil's advocate, is there anybody out there that actually should not consider doing something on the side?

[00:08:07] Stef: [00:08:07] This is a really good question, and the president of my company actually has asked me a little bit about my side hustle and why I'm able to manage these things.

[00:08:16] Realistically, I'm a dog mom. I'm a narrative scientist and I'm a side hustle entrepreneur and I'm a wife, and those identities are really easy for me to manage and balance. If I was a real mom, if I was a full time philanthropist, if I was super involved on, , a nonprofit board or super involved in other companies boards, then it would be really difficult for me to balance all of these things.

[00:08:39] But my point to the president of narrative science, when he asked me that question was. There's so many people out there, right, who sit on the boards of nonprofits and nobody looks at their side hustle and says, well, you shouldn't be doing that. So again, it all comes down to how effective can you be with your time?

[00:08:55] How balanced do you want to be with your life? And do you have, do you have room to fit these things in? Because at the end of the day, we all have, I think it's 168 hours per week. We have to send an email. A bunch of that time sleeping a bunch of that time working. What do you want to do with the extra time?

[00:09:14] If you don't have the time, you can't fit more stuff into the day than it's actually possible. So ask yourself those questions and figure out like, what are you trying to get out of this and is it realistic that you even pursue this? Maybe now's not the time. Maybe there's a time in the future where it will be realistic and then give yourself that grace of understanding what your capacity is and what you can actually take on.

[00:09:38] I would love to

[00:09:39] Blake: [00:09:39] expand more into the side hustle area here. Usually when we're talking about side hustles on this podcast or elsewhere, a lot of times it goes to growth hacking and things that you can do, like tools you can use to growth hack your way to the top. That's very tangible stuff that you can, I mean, you could go find stuff on Google and do that, but I would love to take this a more intangible route and talk more about the intangibles that are necessary to grow a side hustle and make it successful.

[00:10:06] I know that one of those things that you're a big proponent of is raw authenticity, so I would love to, yeah, pick your brain on that. What, what that really means to you, how you can use it for your side hustle and how you can actually use that to your advantage to grow.

[00:10:22] Stef: [00:10:22] So when I think about rots, authenticity, it is truly inspiring people through your own story.

[00:10:31] And everybody's story is, in my opinion, their intellectual property, right. The experiences that you've had can't expand. Others. We just talked about being an expander. Hmm. When we started, manifest. What was raw and authentic to me was I don't want to build a growth hacky business. I don't want to build a seven days till skinny business.

[00:10:55] I don't want to build something that is not sustainable. I wanted to build something. I mean, I do want to build something. Okay. Impacts women at scale across the world. And that's a really, really big vision, right? And so what was authentic to me is taking that 10 year vision cast that I have for our business and then breaking it all the way down and to what was tangible and executable the next day.

[00:11:22] And there are. Practical matters that allow you to move, , allow you or prevent you from moving forward. , capital is something that I think a lot of side house entrepreneurs need to think about. And my self funding this business, is it going to be bootstrapped if it's going to be bootstrapped?

[00:11:39] How much cash do I have in reserves that I'm willing to invest in myself and in my team that I'm putting together? And for me, the answer to that was $5,000. So if I have $5,000 and I have a vision that is frickin massive, then what specifically can I deliver in the next 90 days? That's going to set me on that path.

[00:12:00] And so for us. It was, let's bring 10 women together, all ambitious women from around Chicago, and let's get them to share their stories and let's provide them with value. Let's ask about their biggest dreams and let's have them do our goal setting program so that we can get them started moving in those directions as well.

[00:12:18] So to me, again, raw authenticity is. You have this big vision, you have this big dream or, or you don't, , depending choose your own adventure, but how can you be really true to yourself and like what you were able to take on so you can start moving that vision forward

[00:12:35] Blake: [00:12:35] and expanding on that. Like I know that when, when at least when I am listening to a podcast or reading a book and it says, you need to be yourself, you need to be authentic.

[00:12:43] To me, that comes across as like, okay, that's, that's go good and well, but can I have examples of what that actually means? Because. I am myself all the time. Sometimes I might edit myself a little bit for certain people, but like, could you give examples online? Like if for example, in different formats of posting on social media.

[00:13:04] Okay. What's an example of a way that I could come across as authentic versus it's scripted or like, do you have examples of what that actually looks like when you're being authentic?

[00:13:15] Stef: [00:13:15] So. The way that we extract that out of our community members and , ways that I think about how I can show up as, as raw and as authentic as possible for the people that follow me or follow our business is by asking the questions that nobody would ask you in like a traditional networking environment.

[00:13:34] Like what are you most grateful for in your life? What are you most proud of? Okay. In terms of all the accomplishments that you've had to date. Where are you struggling the most? What makes you nervous or scared? What's your biggest dream for life? Why aren't you pursuing that? ? So getting kind of beyond the surface level questions that you would normally answer or talk about with a stranger and getting deeper into who you are, what drives you, and what motivates you and what you're.

[00:14:04] Bigger purposes on this planet. So I think that if you start asking yourself those questions and getting really in touch with who that person is within you, then you can start showing up more wrong or authentic, , online, even in conversation offline. but it's, it's kind of answering those questions as opposed to staying where most people stay.

[00:14:25] Blake: [00:14:25] Did, do you have any tips for people that are really shy or scared about sharing vulnerabilities in their life? On how to get over that. Like do you have any questions that they should be asking themselves or yeah, exercises they should be putting themselves through to get to a point where they can actually share that about themselves.

[00:14:42] Stef: [00:14:42] So the most effective, professional and personal tool that I have, I've been exposed to to help me feel safe and being raw and being authentic. Is literally calling it out. So I remember specifically two years ago, maybe, maybe a little longer, I was about to present a financial model to a former McKinsey consultant who.

[00:15:04] Knows how to do incredible financial models, right? I've never been trained. He's exceptionally trained. I walk into this meeting, I'm nervous that he's going to look at my dumb, stupid little model and judge it and critique me and make me feel really terrible about it. And so I walk into that meeting and I say, I'm feeling really vulnerable right now.

[00:15:26] I know that you are really skilled here and I'm not, and I'm putting forth the effort and I'm putting in the work. But I want you to know where I'm coming from because if you judge me here, it's going to break trust. But if you support me here, it's going to build trust. And so I felt shy, I guess, quote unquote in that moment saying that.

[00:15:47] But it opened the door for more effective conversation. So if you're shy, if you're feeling really vulnerable, my guidance to you and the best guidance I've been given is just call it out. Let people know where you're coming from so they can show up for you and tell them. Show up for me in this way so we can, we can build this together because this is a really scary moment for me.

[00:16:08] I love that

[00:16:08] Blake: [00:16:08] and I would love to go even deeper in terms of what, what you do a lot at narrative science and what I think you're really passionate about as well as just improving customer experience as well. Just shifting a little bit from the authenticity part, but I'm sure that that plays a huge role in this, but I think you, you view customer service more as a marketing tool than, than anything.

[00:16:29] I'm curious like. How do you use customer experience? How do you use things like word of mouth, authentic communications that are person to person as a marketing tool?

[00:16:41] Stef: [00:16:41] So again, I think going back to this idea of raw authenticity, it's really, really easy in business to forget that person on the receiving end of your product, your service, your communications is an actual human who has actual motivations and dreams of their own.

[00:17:00] And when you think about, Oh, we should run this marketing campaign, or Oh, I'm going to do sales outreach, that's super abrasive, or I'm going to treat all my customers the same. They're just not right. Our customers are people just like us, so I'm always flipping the script. If I was on the receiving end of this communication that was on the receiving end of this call, how would I want to be communicated with?

[00:17:25] How would I want to be supported? And then. With narrative science specifically. The challenge there is to design that at scale so that we can grow our business exponentially. The challenge at manifest is right now it's still kind of delivering those one offs and figuring out how do we scale this? What would...