How to Systemize Your Solo Biz Without Killing Your Creativity

In this episode, I’m joined by Jessi, an operations strategist and expert Asana consultant who helps businesses and nonprofits streamline the way they work. With her blend of emotional intelligence and sharp systems thinking, Jessi shows founders how to build workflows that feel like scaffolding, not a cage—so you can stay creative, delegate confidently, and actually take a breath in your business.

We’re getting real about where to start (hint: what’s painful or costly), which tools won’t overwhelm you, and how to hand things off without losing control. 

You’ll learn:

• The first three things to systemize (based on time/money “leaks”) and a 5-minute brain dump to find them fast
• A simple tool stack for soloists (why Asana Free wins for beginners + when paid tiers make sense)
• The 3 types of delegation (task, strategy, outcome) and how to match the right work to your VA
• How to design people-first workflows (ADHD-friendly reminders, low-notification modes, and a “Someday” sandbox for ideas)

By the end of this convo, you’ll feel equipped to delegate smarter and protect your energy because you deserve a business that feels good! 

About Jessi Engelke:

Jessi is an operations strategist and expert Asana consultant who helps team-based businesses and nonprofits streamline the way they work. With a background in corporate and nonprofit leadership, she blends emotional intelligence with sharp systems thinking to bring both calm and momentum to overwhelmed founders. Jessi specializes in building people-first workflows that boost team efficiency, improve client experience, and make sustainable growth feel possible again. 

Her signature approach centers on simplicity, emotional safety, and practical delegation so CEOs can focus on leadership instead of logistics. Through her company, One Stone Solutions, Jessi supports service-based businesses that are ready to scale with intention and lead with more ease, not exhaustion.

🔗 LINKS & RESOURCES

• Connect with Jessi on LinkedIn
• Need a simple system? Find out what Jessi does here

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Transcript

Natasha (00:00)

Hello and welcome to the show, Jessie.

Jessi (00:02)

Thank you for having me excited to be here.

Natasha (00:05)

I'm so excited about this topic because I think that, you know, project management and organization can make such a difference in your business, especially for your sanity. We're always, you know, struggling with time management and all of the things, and this just adds such a beautiful piece to your business that will give you that piece that you're looking for. So with that said,

Jessi (00:26)

quickly.

Natasha (00:28)

I'd love to jump in and just ask you a lot of solopreneurs hit that tipping point where they know they can't do it all alone anymore, but they're really just not sure where to start with these systems. How do you help people figure out what to systemize first?

Jessi (00:44)

I start with what's either painful or costly. Where is the time, energy, or money leaking? My intake questionnaire says, what do you have to do every week or every day, even if you're feeling sick, tired, or over it? And so the answers to these questions tell me if it's a scheduling tool they need, a project management tool they need, or a CRS.

Natasha (01:08)

Yeah. those pain points, man. And do they hit home? Like where are you bleeding money and time? That's a great place to start. What are your go-to project management tools and software for small teams that, you know, and solo printers that make a big difference without like overwhelming the user?

Jessi (01:11)

Seriously? Seriously?

So I'm a certified Asana consultant, so there's a correct answer to this question. I love Asana because it's so simple and a lot of people don't know that there's a free version that's perfectly suitable for solopreneurs. You just need a place to put the tasks that you need to do on a regular basis and you need reminders for when it's time to do it again. Paid tiers in Asana start to make sense when you're ready to delegate or you need to do some heavy reporting.

Natasha (01:32)

you

Jessi (01:55)

⁓ I caution against tools like ClickUp or Notion if it's the first time you're setting up a project management tool because you can kind of get lost in the onboarding. It's very complicated. I hear from other folks all the time that they love hearing about other, they hear from other solopreneurs that they use ClickUp or Notion and then they try to get in it themselves and it just, the onboarding is so overwhelming that they just like let it go.

Or they set it up at a time when they had all that time and now they don't have that time and they need something more simple.

Natasha (02:28)

Yeah, I think that's a great point. And I can think of an example where I came into a company and they actually had like probably a 12 seat, like, you know, of Monday. So that's 12 users and they're paying for it and not a single person was actually using it. And so I came in and helped set that up for the team. But

Jessi (02:39)

Yeah.

Yeah, ⁓

Natasha (02:47)

that we really needed to set up a system within the project management tool. It's not necessarily that you just get it and everyone knows how to use it. There's a training and all of these things that need to happen. So I really resonate with what you said. I think that is so important.

Jessi (02:51)

Yeah.

Yeah.

Yeah.

Natasha (03:03)

So before someone brings on a VA, because there's a lot of talk about bringing on a VA, but there's pieces that need to be in place. So what should a business owner have in place so they're set up for a smooth, productive working relationship from day one when they bring in help?

Jessi (03:20)

I love this question. First is I would caution not to wait for perfection, but wait until you're at a point where you are ready. Sometimes we can get caught in making sure we have all of our, I was working with a business owner not too long ago. She was adamant that she needed to write all of her SOPs in perfect condition before she was ready to bring on anybody. And that day never came. The perfect condition never came.

Natasha (03:47)

And meanwhile, she's probably getting busier and busier, right?

Jessi (03:50)

Yes, exactly,

exactly. And so you need a list of clear recurring tasks, daily tasks, weekly tasks, monthly tasks. And if you're not sure what these things are, just monitor your own activity for a couple of weeks and keep a list of the things that you're doing on the regular basis. Some sort of system to share passwords.

Natasha (04:09)

I love that assessment advice.

Speak into my heart here. Which, which tools do you like the best for that?

Jessi (04:15)

Yes.

I see LastPass as a very popular tool, though the cybersecurity community would encourage us not to use that tool. ⁓ One password is another suitable option, but having anything in place is better than just emailing your passwords all over the place and not having a way to revoke.

Natasha (04:37)

That's my opinion as well. I have LastPass and I know that there's different opinions, but at the end of the day, most of the people, ⁓ I see their passwords and LastPass is going to be better than your child's name and birthday.

Jessi (04:45)

Yes.

Yes.

Yes.

So a clear list of the recurring tasks, some way to share passwords safely and a lightweight SOP. It doesn't have to be a 19 page document with screenshots. It can be a bulleted list or it could be just that loom video. A lot of folks will hire a VA and allow that person to fully flesh out their SOPs. You just need enough for them to get started and then it can be their role because they're in it all the time. You're not in it anymore.

It can be their role to complete that SOP for you.

Natasha (05:27)

Yeah, and I think that's a great point because sometimes, like you said, the other gal's waiting to create all these SOPs to bring someone on. But you could bring someone on who could write those SOPs, and then that's done for you because you just don't have the bandwidth. ⁓ Perfect. Yeah, I think that's wonderful advice. And I love the assessment. Just sitting down and assessing what you're actually doing is going to tell you a lot about your processes and what you need.

Jessi (05:40)

Exactly. Exactly.

Hmm.

yeah.

Natasha (05:51)

So what are some of the biggest mistakes you see solo printers make when they just try to hand stuff off without like any kind of process, even that like that light SOP that you mentioned?

Jessi (06:00)

Mm.

Attempting to hand off processes that are not suited for the person doing them. I have a freebie on my website called the delegation toolkit and I talk about the three different types of delegation. ⁓ Task-based delegation, this is stuff that's suitable for a VA, the repeatable rinse repeat tasks that happen all the time, they're very clear and they're also kind of tangible, binary, it's either done or it's not. The statements are either downloaded or they're not. The post is either posted or not.

And then there's strategy-based delegation where you have a higher level resource like maybe an OBM or strategist of some kind who can give you advice about the strategy that you need to follow. And then there's outcome-based delegation where you're bringing on somebody who's your equal within the organization, a chief of some kind. This person owns a whole section of your business. And what I'm finding is solopreneurs are often in their overwhelm or haste to delegate.

will give a VA all kinds of tasks, the tangible tasks, the strategy tasks, the outcome-based tasks, and just that's a recipe for failure for everybody. You're frustrated that the thing didn't go as planned and the person who's trying to work for you is frustrated because it's just not suited for their level of experience or the pay range they're receiving.

Natasha (07:29)

Yeah, and some of that's kind of trial and error if this is the first time you're hiring, but I think you can think about those things upfront, like know that that's a gap and try and find the right fit. And then, you you might just have to learn. For those listening who aren't familiar with the term OBM, can you define that?

Jessi (07:46)

sure, online business manager. This is somebody who owns operations with your business. They're not quite chief level resource, but they're also not a VA either. Project manager is another term that I've seen thrown around.

Natasha (07:48)

Okay.

Okay, perfect. That's helpful. And you talk about building people first workflows. What does that actually look like when your team is just you and maybe one other person?

Jessi (08:12)

So I'm focusing on making the workflow work for the person that's using it. For example, if it's somebody that's super forgetful, I'll configure Asana to show them where the reminders are. And we turn on the email reminders and show them where the calendar is. I show them where the inbox is so that they get those daily notifications. These are the things that you need to work on today. ADHD brains love this. And if it's somebody who...

maybe doesn't need a lot of those notifications or they find them extremely disruptive, like our autistic friends, I turn off all of those notifications. And if they're visual, then we embed a lot of loom videos and screenshots. So it's really about what that person needs in order to follow the workflow as opposed to, well, it's already built, so you just follow what it says. And so we don't resonate with those type of instructions and we need them to be configured in a way that makes sense.

for us as people.

Natasha (09:09)

Yeah, I love that approach and really considering the individual because everyone has different learning and implementation styles. And I know I use Monday as my project management tool. I think one of the things, and I know Asana is similar in this, is that there's all these different filters. So you can actually look at things differently. So you can have all the same tasks and information, but it can be looked at differently for different people and their needs. So I think that's the beautiful thing about these tools as well.

Jessi (09:33)

Mm-hmm.

Exactly.

Natasha (09:39)

So I think a lot of solopreneurs, especially creative ones or ones running low on time, they resist systems because it may feel limiting and like it boxes them in. But how do you design systems that actually keep flexibility and creativity intact?

Jessi (09:57)

This question comes up all the time. I would say if you feel boxed in by your system so you feel like they're a cage, then you need to break them because they're not working for you anymore. A truly supportive system should feel like scaffolding and it should feel like it's helping you along and not making you feel totally stuck in something. I do this by making sure that we're working with or developing minimum viable systems first and not

wholly complete, super complex systems as the first point of entry. We're keeping things really simple at first and we iterate on them over time. So instead of having a phased approach to, or cyclical tasks that have phases, I keep them to three at first. If your system has 17 different phases, I would say that that's actually separate processes that need to be broken apart. And it really needs to be as simple as possible. I also like to make ⁓

Natasha (10:52)

Yeah, I love that.

Jessi (10:54)

little sandboxes or brainstorming places. Folks that have ideas that sort of like pop in their head at a moment's notice love having a place to just put it to think about later. I have a someday, I have a someday place at my asana and I tag tasks that are someday when I have time, when I have that help, when I have more capacity, et cetera. But that way I'm not like carrying that with me throughout my week. I have a place that I can go when I do have that someday.

Natasha (11:25)

Yeah. And, ⁓ one of my previous guests on the podcast, Marie Reginado, she said that, you know, she has something similar because inspiration, doesn't necessarily hit you. Like when you're sitting down to work, like you might be out for a walk. And so you just want to jump in your system and just jot it down and then come back to it. Maybe when you are working, but that inspiration is just, it's free flowing. just comes to you when it comes to you. Wonderful. So delegating.

Jessi (11:46)

Yeah, exactly.

Natasha (11:53)

can really feel scary, especially when you've been doing it all yourself. People have a tendency to not want to let go. What is your advice for letting go without feeling like you're losing that control?

Jessi (11:55)

and

Mm.

Yeah,

yeah. Start small. Start with a thing that will not tank your business if done correctly, or done incorrectly, excuse me. And then allow your nervous system time to feel that as safe. And so I start with, I like to trust people obviously, but I also start with like an internal 30 day ⁓ onboarding period where I don't allow somebody access to my entire system all at once. They have

sort of a playground that they play in for the first 30 days and I see how they respond to certain tasks and I allow myself time to feel that safety of, okay, they handled this one, okay, they handled this one, they handled this one, and then that becomes a snowball effect for bigger tasks.

Natasha (12:50)

Yeah, that's a really great approach. And I think that also helps your employees feel confident. Because I think sometimes people come into a new workplace and we have this perception that we need to know everything day one. But I think the best advice I've ever gotten is that it takes six months to feel comfortable in a new role. And so what you've structured is really modeled after that and feels successful and thoughtful to me.

Jessi (13:01)

Yes.

Yes, agreed.

Natasha (13:16)

So for someone listening who feels behind on systems and they're already overwhelmed, what's one small thing they could do this week that would make an immediate difference for them?

Jessi (13:27)

I have an activity I sometimes do with folks. It's just a brain dump. Pen and paper, write down, set a timer for five minutes, write down everything in your head. Everything. Don't filter. Just write it down. And then circle after the, the end of five minutes, circle things that are your top three priorities. That's sometimes hard to do because it feels like everything's a priority, but try to limit yourself to the top three. And then, ⁓

with another color pencil, right, a circle, anything that's just a random thought. I'm hungry, my shirt itches, like whatever. And then anything else left that's not a three, one of your three priorities or a random thought is a task that you need to complete. And so you put all of that in your tasks, but you start with those priority threes.

Natasha (14:17)

Yes. And I, my lucky number is three. So I love threes and I've, I feel a lot of magic in it because I feel like I can get three things done in a day. Like obviously I get more, but like when I write out my tasks, like I know I can get three things done and then other stuff will happen around that. But if I do more than that, it just, maybe I get one done. ⁓ perfect. So I know that you work with folks. So can you tell us a little bit about your services where people can connect with you?

Jessi (14:21)

this, right?

Yeah.

Right, exactly. Exactly.

Sure. My website is onestonesolutions.org. That's O-N-E-S-T-O-N-E dot O-R-G. I have been focusing a lot on setting up Asana systems for solopreneurs and teams. And so I have a service for both somebody who needs to move into a solution for the first time. Maybe they're using a lot of sticky notes and they have a whiteboard, et cetera. I have a service that will set up their Asana account within seven days using the free version.

And then for teams that have been using Asana for a while, I have a rescue where I'm actually working with a company right now out in California who has been using Asana for the last four years and have respectfully made a right mess of it. And so now it's my role to help them make it a little bit more streamlined so that they can grow their business. They're in a really great, exciting time in their business. And so we need to clean up some of the noise so they can expand.

Natasha (15:44)

Awesome, that's great. And as we wind down the podcast, I always love to ask people what's one piece of advice you would give your younger self.

Jessi (15:56)

You don't have to earn rest by hitting rock bottom first.

Natasha (16:04)

That's a big one.

Jessi (16:04)

You really

do need those, those breaks. And they're part of the reason that you are so successful is taking breaks. And so I've always sort of felt like I don't get to rest until my things are done. And because my task list is so long, I'm kind of an overachiever. That time never really comes. And so I've dealt with burnout in my, business and in my W2 life. And so the things that have helped me overcome that is just blocking out times for breaks.

in my day. It's mandatory five minutes on the porch like a lizard absorbing the sun. And that has really has really done a lot for me.

Natasha (16:43)

I think that advice is so powerful and I think a lot of entrepreneurs struggle with that. actually think this is one of the more frequent answers is, you know, not being so hard on yourself or scheduling in that time. You know, you're worthy of that just because you exist, like to enjoy your life. I really love the perspectives you've brought to the podcast today. I think you're very thoughtful in the way you approach things and I've really appreciated having you on today.

Jessi (16:51)

Yeah.

Yeah, exactly.

Thank you, I really appreciate that.

Natasha (17:12)

All right, we'll see everyone back in the next episode.

Jessi (17:16)

Thanks, y'all.