682: Beating Side Hustle Burnout: 14 Strategies for Sustainable Success

24:39If you can see that light at the end of the tunnel, maybe a sprint is in order. William Wadsworth had a similar line. He said, if you're bored walking up the hill, try running up it. Maybe speed can be a secret weapon. And if I'm running away from something I hate, like a toxic job or an angry bear, I can probably sprint longer and harder than I normally could. But every sprint has to have an endpoint. And if you don't have a specific direction and milestone to know when you've made it, I would hesitate to recommend that strategy. One interesting twist on Rachel's sprint strategy was Drew Ackerman's idea of setting somewhat arbitrary quit dates for his side hustle.

25:16Here's how he explained it. Hey, this is Drew Ackerman. I make Sleep With Me podcast, a podcast that helps grownups fall asleep, a little bit like a goofy friend telling you a bedtime story. I started the show in 2013 just as an experiment of like, how come there aren't silly bedtime stories for grownups? And would anybody listen? Would the idea even work? and one of the most effective things for me was setting quit dates where I was like, okay, I would have a meeting every few months and say, do I want to keep making this podcast or not? And usually it was like, oh, of course I want to. You know, there's a few people listening or it helps these people fall asleep.

25:58But in between those quit dates, it really helps not silence my internal critic or the other parts of me that are kind of obstacles a lot of times for getting stuff done. But it helped me say, hey, let's just keep working on this until the next quit date because I just have this internal critic that's like, oh, this is a bad idea. This isn't working. This isn't successful. And I would give my critic full voice at those meetings. But in between the meetings, they'd say, hey, can we just save this for the next meeting? And that really helped me keep the podcast going over, I think, like three years is really where it started to finally gain momentum.

26:34them. The second thing I did was talk to my listeners about sharing the podcast and just ask them, hey, if you get value out of the show, just share your honest experience with that. And letting them know how incredibly powerful word of mouth is, because I don't think everybody knows that. And then thanking people when they did share the show. And so that's where a lot of growth happened. And then after making the show for about four years or so, maybe three years, I started Patreon. I tested out podcast merchandise, affiliates, sponsors. And in 2017, so I started the podcast in 2013. In 2017, I would say the podcast became my side hustle, and I slowly started to use up my vacation at my day job and started to cut back my hours at my day job from full time to three-quarter time to eventually half time.

27:27And then in 2018, I was able to leave my day job as a librarian and work on my podcast full-time. And between Patreon, merchandise, sponsorships, and a few other things like affiliates and stuff like that, I'm able to do the podcast as a full-time job, pay for health insurance, put some money aside for retirement. Very similar to what I would expect if I was looking for a job. I've also been able to build up an emergency fund, a personal emergency fund, and a business emergency fund, because a lot of my goals around finances with the podcast are making sure the podcast is sustainable and high quality and delivered on a regular basis.

28:06But it started as something almost like a hobby, an experiment, that I just kept going. I kept working at it and trying to make it a little bit better each time. Now, a couple of things here. I love Drew's example of scaling slowly back at his day job as the podcast grew. Doesn't have to be all or nothing. And I love the idea of setting a quit date 90 days in the future, six months in the future helps you avoid the day to day decision fatigue of whether or not you should keep going. And I imagine had Drew come to one of those quit date meetings with himself, by the way, just him, and found he no longer enjoyed doing the show, it wasn't seeing enough traction, he would have had the discipline to say, I'm going to retire this project, I'm going to see if there's another side hustle that makes more sense.

28:50So that's strategy number nine, put a quit date on your calendar. I do this for all kinds of side hustle experiments. Hey, we're going to test out a new content strategy. We're going to give it 90 to 120 days. We're going to see what kind of results or return on investment it generates. And we're not going to question it. In the meantime, we're just going to collect the data. We're going to re-evaluate it then and see if it makes sense to keep going, to pour some fuel on it, or to pull the plug. Now, let's say you're running your business and the stress is mounting. There aren't enough hours in the day.

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31:37Terms and conditions apply. Hiring. Indeed is all you need. in my original side hustle my online shoe business there would be times i would crank away on that site 10 12 plus hours a day maybe even more when when brin was out of town maybe 14 hours a day sometimes it was pretty tedious work not quite data entry but definitely not rocket science either the challenge that i felt was like every hour i didn't work it felt like it was costing me money especially during the busy season of Q4. I was problem aware, as they say. I knew I should probably get some help, but I had all the usual hang-ups of not knowing how it would work payment wise or cost wise or tax wise.

32:20I was afraid that any assistant I brought on would like steal my ideas. I didn't have the time to train anyone. All the usual excuses. It was 100 % a case of being too busy chopping down trees to sharpen the saw, which is why strategy number 10 is to hire some help. Even though the website itself had leverage, it could make sales when I wasn't working. I still felt like I needed to work on it all the time. When I finally hired my first assistant, it was a huge shift. And that's not to say everything was perfect right out of the gate. There was a one step back before taking two steps forward kind of thing, where it took some time to vet and interview candidates.

32:59It took some time to document processes that up until then had only existed in my head. It took some time for training. And no, they weren't as fast or as quote unquote good as me at these tasks. But after that, after bringing on this person, this first assistant, something magical happened. And that magic was work getting done when I wasn't working. That was a big unlock. And yes, it cost some money, which was another one of my hangups. I could just do it myself is always my excuse, but it was well worth having some breathing room in my day and not feeling like I had to keep grinding 10, 12, 14, 16 hours a day.

33:35Now to get started down the delegation path, if you've never done it before, my recommendation is to start with a time audit. This is tracking for a couple weeks what you're actually spending your time on. And if you're anything like me, you might find that you've got a lot of hours spent on relatively low level administrative or repetitive tasks that with a little guidance, a little documentation, a little training, an assistant or another hire could reasonably take off your plate. And there's a couple different flavors of outsourcing. The first, which I just described, is when you take something you're already doing and hire somebody to do it for you.

34:15The second is perhaps a little more advanced, and that's to hire for the stuff you don't know how to do. Here's John Jonas from onlinejobs.ph and Nate Hirsch from our episode on hiring your first virtual assistant, describing those critical hires. So what I tell most people today for like, when do you know is when's the time to hire someone? Because for me at the time, it was like, dude, I don't want to do this. I don't want to do this thing that I'm doing. I hate this. So I had to try and find help. what I'll tell most people is if there is something that you're doing that you could potentially teach someone else doesn't matter how much work it takes you to teach someone else it's time to hire someone else it's time to hire someone else to do it because if it takes you a month to teach them how to do it after that you'll never have to do that thing again if you've hired correctly you'll never have to do it again and that is the only way that I know of that you can buy time yeah it's kind of this saw sharpening moment where you have to take, again, you're already pressed for time, you're already busy and say, well, now I'm going to take time away from doing that thing to train somebody else to do it in the hopes of never having to do it again.

35:29Like it's going to take me this time up front. It's this investment in your future, the only way to buy time. Nate, anything to add on that? Like for when is it time to hire? There's really two schools of thoughts. I mean, the first one is exactly what John said, when it's all these things that are just piling up that are taking on your time and the only way to get your time back is to pass those tasks off to someone else. And how do you get five hours in your week back, 10 hours in your week back, whatever it is. The flip side of it is I think the average entrepreneur is only good at one to three things, their core competency.

35:59Maybe you're good at sales or you're good at content or whatever it is. And as you get farther and farther away from your core competency, sure, you could take a six month course to become a Facebook ad guru, but you can't do that with every single part of your business. So at some point, you have to hire people who are better at doing things than you are. And it could even be the small stuff. I mean, take the bookkeeping, for example. I wasn't necessarily great at just transferring information and making sure everything's accurate and double checking it. I mean, that was very tedious for me. That's probably not my core strength.

36:31So I take someone else and I put them in it. And not only are they doing the job, but they're doing it better than I could have done it originally. So I think that was a big eye opener for me as well when I would give someone a task and maybe not right away, but eventually they would do something even better than I could. And that's very liberating. And it makes you want to delegate. It almost makes you want to be a lazy entrepreneur, so to speak, really just toning in on what are you the best at, what helps you scale your business and finding ways to delegate everything else. Definitely a worthwhile episode to check out in full if you find yourself as the bottleneck in your business.

37:04It's episode 343 in your archives. And I know we've re-aired it at least once as a greatest hits episode. and I've used several different sites to connect with assistants over the years, from johnsonlinejobs.ph to Upwork and Fiverr to more specialty services and even our sponsor, Indeed. But the key is to define the role, to set clear expectations and rip off that band-aid. You can't expect to do everything on your own. It's no wonder you're burnt out. Chris Ducker calls it superhero syndrome. But if you want to go fast, go alone like the old proverb. If you want to go far, go together. Get some help.

37:39Really grateful for the team I have in place and all the work they do to get these episodes ready for you every week. For any given episode, there are four or five team members all doing their part. Stuff I used to do all on my own starting out, but slowly chipping away at the tasks where I'm not adding much value. Now, as your business grows, you might find yourself kind of out of your league or what made it fun early on is no longer the case. When I chatted with Justin Tan from Video Husky, he took a really interesting approach in essentially outsourcing himself as the CEO? I was quite burnt out.

38:11I think the back-to-back crisis made me realize that number one, I did not enjoy management. I'm not really somebody cut out to ensure the day-to-day and the week-to-week, everything aligns and we're moving forward in the right direction. And I think doing that properly for a year really taught me that lesson. And so I started considering other solutions, whether it was just minimizing my own role or, while not really selling, just seeing ways that I could step out. Yeah. What was the day-to-day? So you mentioned, I got to manage this huge team. Are you still running marketing? What's your role?

38:50Yeah. So at that point, I was still running marketing and we still had our set of weekly calls that had to happen to ensure things ran smoothly. And I think as we went through more and more of those, as we set a good weekly cadence, I just realized that there was a pretty big disconnect for me personally between both me and our clients because I personally am not a video creator. I don't know how to film. I don't know how to edit. I don't know how to, I guess, promote. I don't particularly enjoy promoting myself or our editors because I don't have a creative eye. As I said already, I don't know how to edit.

39:21And so I realized that lack of sort of founder market fit and founder product fit was really hindering, I guess, my own ability to apply myself in Video Yoski. Okay. So you think, well, it may not be sellable where it's at today, or I'm not quite ready to let go of it, but I do want to outsource myself from the day to day. I want to bring in somebody else to be the operator, the COO in a way. Is that what happens? Yeah. So it was around, I think, beginning of 2021 that I started working with another coach, Taylor Pearson. And so working with him kind of made me realize, okay, this is really not my role.

40:01Even though, of course, like at the end of it, I am responsible for videoski. I feel a lot of responsibility for the team that I just could not continue on a day to day basis. And he kind of outlined the consequences of a person running a team when they're already burnt out. And it turns out that this is a thing around the four to five year mark, a lot of founders get burnt out. And the key is to kind of already have a team in place that you can transition to so that when that burnout inevitably happens, your team is still good to go, your business is still good to go and it can run without you.

40:31Yeah. And so he was the one who outlined kind of like what a sale process would look like and what the multiple would be, which wasn't all that attractive to me, just because it's three to four times earnings, five, if you're really lucky, compared to the idea of, let's say, bring out a general manager where I personally might earn a little bit less, but it would mean that the business would continue to spend out dividends, which would be enough to live off of while the GM would have the opportunity to grow the business while reducing the kind of key man risk that the business was relying on me, which also ironically makes it more sellable in the long run.

41:07Yeah, I was, and this is an interesting kind of fork in the road. And I won't name names, but I was talking to some friends at FinCon who had gone down, maybe not a completely similar path, but you know, they went down the path instead of, you know, doing a clean, one and done, cut me a big check, I'm getting out of here, sell the business, exit. They went down the path of kind of bringing on a partner with the hopes, well, maybe the partner can grow the business. I'm kind of in this burnout phase. I don't really want to work on it day to day. But then the partner ends up just tanking everything.

41:37So it's a huge risk for you as the business owner. They can take what we've already built and they can take it to the next level. But they could also screw things up. They could also upset the clients. They could also upset the team. They just might not be the right cultural fit. Like, you know, we might have another crisis where 30 % of the clients leave again. Like it's a risky proposition versus, you know, almost taking the money in and just, you know, washing your hands of the whole thing in a sale. Yeah. And so I think that was something that I was willing to give a shot for. So the way I figured it was the absolute worst case scenario is that if it turns out he's not a good fit after one, two, three, six months, well, I guess I'll step back in and I'm exactly where I'm at.

42:22But at least I had a three to six month break, which maybe would be enough kind of fuel to get started again. But while there are downside risks of potentially doing worse than what Video Husky was, there was also the upside risk of doing better than what Video Husky was previously doing. And in my head, it made sense because at the end of the day, I have limited business experience. I had never managed a team of 50. So I inevitably would have made a lot of mistakes versus bringing on somebody who had that experience, who had already worked at a higher level than where I was at. I think there was something to be said about that kind of know-how that I really wanted to bring to Video Husky and our team.

43:00Because not only am I, but our entire team is just so young that we can either learn from experience or ideally learn from other people's experiences and get to where we want to go faster. again that was justin tan from episode 540 really powerful episode on a side hustle that turned into a pretty big business and all the trials and tribulations along the way plus did you catch the part where he said he wasn't a video creator or a video editor but still managed to build one of the most popular video editing services for video creators really cool example of not needing to be the expert to solve a problem but playing matchmaker instead so that's number 10 that's the delegation piece?

43:39If you're burnt out or overwhelmed, what's one thing you can get off your plate this week? How can you start chipping away at these tasks and start leaning more on your team so the business maybe can start to run a little bit less without you? You start to be a little bit less of the bottleneck. And you may not even need to delegate it. I mean, if it's really that important, if it's not really that important, you could just eliminate it. Or you could ask ChatGPT if there's a way to automate it. You might even upload your time log into Chatty and ask for some recommendations on what to outsource next.

44:10That's number 10, hire some help. Number 11 is to sell the business. Like Justin mentioned, if you can make the business less reliant on you, the more sellable it becomes down the road, which might be the ultimate way to beat burnout, cash out, be done with it. This was a fail of mine holding on too long to the shoe business. In hindsight, I could have exited. It might have been worth maybe half a million dollars if I timed it right. And I could have used that runway to figure out the next project. Because as entrepreneurs, we're always looking ahead for the next thing. And I've found that having an exciting new project or experiment tends to breathe some new life into an old business.

44:46That's why that's number 12 is to change up the routine and spark some creativity. And sometimes that creativity gets sparked just by changing up my routine, working from the coffee shop instead of from home, visiting a new city, going to a conference, taking some time off with the family. Because it feels new and different and exciting, even if it's adjacent to what you're already doing, I feel like I attack it with some more energy and enthusiasm than I would if it was just the same old, same old. And this is super common in startup culture and maybe should be a little more so in side hustle culture, but it's the idea of a pivot.

45:21This is number 13. If you're burnt out and you're not seeing the traction or results that you like in your current business, maybe it's time to consider a pivot. One of the most inspiring and profitable examples of that from the Side Hustle show comes from Abby Ashley in episode 284. She'd already replaced her day job income with virtual assistant work and even built a small agency at one point. But she had this itch to grow it even more. She just wasn't sure if taking on more clients was necessarily the right path. I was starting to get a little burnout on client work. So I got actually I got a few more clients because, hey, I needed money and I knew how to do that.

46:00Well, I knew how to get clients. So I grabbed a few more clients and started working again and still just devoting a lot of time to trying to figure out what I was going to do. I actually stumbled upon a podcast in fall of 2016 about discovering your niche. And it was so funny because I had hired a business coach. I had really done so much soul searching and this one stinking free podcast totally just made me think, I just need to teach or like, I need to ask my audience and teach what I'm actually good at, like what I've had success at. So rather than creating courses, I had the idea. I didn't just say, you know, what do you want to learn in general to my email list?

46:43I said, hey, I have this idea for creating a virtual assistants course. I created this agency. I was able to quit my job doing virtual assistants. I thought up what like the modules for the course would be. I just listed them out. And I asked if anyone was interested in that topic. If so, I was going to sell the course at a lower price. It was about half the price around, I think it was like$400 or$500, where I knew eventually the course would be probably a$900 ,000 product. I said, Hey, you can get in early. And I had about 16 people buy from my list of a thousand. So I made$8 ,000 from doing that tactic, just asking people before I even created the course, is this something you would want to learn?

47:27Here's the modules. From doing the thing to teaching other people how to do the thing. Here was a low risk, low overhead pre-sale validation. She hadn't recorded anything. She just had outlined it and said, hey, is this something that would be a fit? I think in that episode, she goes on to describe that the sales page she used was a Google Doc. Really, really lean startup style. really cool. So is there something new you could sell or even pre-sell to your existing audience or customer base that would reinvigorate you to the business? For me, what's gotten me excited lately is some process improvements, usually powered or assisted by AI, coming up with new episode ideas like this, new affiliate partnerships to test out, or creating new digital products.

48:09It was a question that came up lately with a friend of mine. He said, dang, I can't believe been doing this show for 12 years. I was like, you know, time flies when you're having fun. But he asked if it got boring or felt repetitive. And the answer was an immediate no, which I took as a good sign. There are repetitive components to the process, but the individual stories and strategies will keep it exciting and such a fun, creative outlet for me. And that creative constraint of six times a month, we've got to come up with some compelling radio to share and how we're going to fill in those boxes with something that is hopefully helpful on the side hustle front.

48:45So that's number 13. Consider a pivot. if you're feeling burnt out in your current work. Like, okay, what is adjacent to something we're already doing that we could use the existing skills for? Number 14 is this mindset shift of I get to versus I have to. Now, this definitely doesn't apply if your burnout is the commuting two hours each way to a job I hate that barely pays the bills variety, but it definitely applies to side hustlers and entrepreneurs who chose their path, right? It's a privilege to get to be the boss. And it might feel like we have to get up and work on our business today, but we get to.

49:24It's a unique chance to help our customers, to learn new skills, to connect with people in a meaningful way, and hopefully improve our financial well-being along the way. Now, I remember not being a lot of fun to be around leading up to my TEDx talk, where every spare moment was spent rehearsing in my head. I may have been physically present, but I wasn't there mentally. I was like, you know, stressed out. I was losing my appetite. And at one point, my wife goes, just remember, you chose this. And she was right. I volunteered for it. It didn't necessarily make me any less stressed, but it did put a smile on my face.

49:55And it was an important reminder of get to versus have to. And that's where I want to wrap this one. So to recap, we covered how to prevent burnout and some different tactics that you might find effective in reducing it in your own life. We started with finding your why and try and go five why's deep. Why is it important to you? Why do you want to do this? Talked about your five-year perfect Tuesday exercise, kind of this visioning exercise and how to start chipping away at that in small ways today. How can I get closer to my perfect average day today? Talked about the importance of a nightly shutdown routine.

50:31When I get done, I'm going to recognize and celebrate the progress that I did make. I'm going to be grateful for the positive things that happen. And I'm going to prioritize my next day. How am I going to win tomorrow? Talked about building sustainable systems. We talked about avoiding the comparison trap. Easier said than done. Talked about the importance of taking care of your physical health, your fundies, your sleep, your diet, your exercise, and the impact that that can have on your mental well-being as well. Talked about finding a creative outlet. Whether or not it turns into a side hustle doesn't have to be.

51:02Don't put that pressure on yourself. Talked about this balance of persistence plus patience with the example of Sile. Hey, I worked for nine months before I started to see any meaningful revenue here, but I was afraid to stay where I was. And this goes back to the finding your why. That persistence plus patience piece. We talked about, in certain cases, a short-term sprint might make sense. If you could see the light at the end of the tunnel. Remember Rachel? Oh, she's like, I felt like I was drowning, but I could see the light. I knew I could get myself out and free up an extra 40, 50 hours a week.

51:32We talked about giving yourself a deadline. We talked about setting specific quit dates, three, six months in the future to say, I'm not even going to be allowed to question this until then. Or we can address that at the next quit date meeting. We talked about delegating, outsourcing the parts of your work that don't light you up. Talked about the optionality to potentially sell your business, something I did with a website of mine in 2020. We talked about the idea of keeping your work fresh, changing the routine, sparking some creativity. Talked about maybe doing a pivot where that might make sense.

52:05And finally, the mindset shift of I get to versus I have to. If you're battling burnout, don't just think it'll magically go away. I encourage you to seek out some professional help beyond the advice of your friendly neighborhood podcast host. I will also link up the individual episodes that we heard clips from in the show in the show notes for this episode. Just follow the show notes link in the episode description and it'll get you right over there. As I mentioned, the Side Hustle Show recently had its 12th birthday. It's almost a teenager and like you heard, there's a lot of gold in the archives.

52:36You just got to know where to find it. And to make that easier and hopefully more relevant for you, you can actually get a personalized side hustle show playlist at hustle.show. Just answer a few short multiple choice questions and it'll recommend 8 to 10 of our greatest hits based on your answers that you can add to your device, you can learn what works, you can go make some more money. Again, that's hustle.show for that short personalized playlist quiz. Big thanks to all our guests over the years for sharing their wisdom on this important topic. Thanks to our sponsors for helping make this content free for everyone.

53:09Where do you go if you want to see all the latest offers from our sponsors in one place? Stay with me. SideHustleNation.com slash deals is that place. Thanks for supporting the advertisers that support the show. That's it for me. Thank you so much for tuning in. If you're finding value in the show, make sure to text a friend. Until next time, let's go out there and make something happen. And I'll catch you in the next edition of the Side Hustle Show. Hustle on.