Confused by Instagram? This Episode Will Fix That

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Think Instagram is just for influencers and avocado toast? Think again. In this episode of The Aspiring Solopreneur, we sit down with Sydney O'Brien, a rockstar Instagram strategist who built her business while juggling three kids under five and a military deployment (yes, really).

Sydney shares why most solopreneurs are talking past their dream clients, the mistake you're probably making with your hashtags, and how to stop letting engagement (or lack thereof) ruin your day. 

From easy tools for beginners to the secret behind getting real conversations started in the DMs, she breaks down Instagram in a way that’s actually doable and even fun.

If Instagram makes your eye twitch, this episode is your cure. Tune in and get ready to rethink your whole content game.

Like the show? We'd love it if you'd leave a 5-star review!

Connect with Sydney O'Brien

• Connect with Sydney on Instagram at @socially.yours.strategist
• Listen to Mompreneur Mastery
• Access Plan It. Post It. Profit.

Favorite Quote About Success:

"Success is doing the things most people don't have consistency for." - Serena Williams

Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr Intro gives you free education, community, and tools to build a thriving one-person business. 

So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, click here to check out LifeStarr Intro!  

About Sydney O'Brien

Sydney O’Brien is an Instagram strategist who knows what it’s like to build a business in the middle of chaos. She launched her company while solo parenting three young children—including a baby—all while her husband was deployed with the Air Force. As a mom of neurodivergent kids, she understands the unpredictability of everyday life and uses that experience to help other moms grow businesses that work in the cracks of their day.

Sydney helps overwhelmed mompreneurs ditch the fluff and use Instagram to build real, lasting connections—with clients, community, and fellow moms. Her content strategies focus on authenticity, simplicity, and sanity-saving structure—turning followers into customers without adding stress.

Episode Transcript 

Carly Ries: If you've been listening to the show, you know that Joe and I are not Instagram pros. We're not even social media pros. So in this episode, we're joined by the strategist behind at socially.yours.strategist, Sydney O'Brien, to finally get answers to all of our burning questions. Do hashtags still matter? What actually works works on Instagram now?

And how do you post without spiraling into an engagement induced identity crisis? Sydney shares the must know strategies solopreneurs need to actually connect with their dream clients, batch content without burning out, and maybe even, dare we say, enjoy using Instagram. So whether you're totally new to content creation or just tired of hearing crickets in your comments section, this one is packed with clarity, laughs, and actionable advice. You're listening to

Carly Ries: the Aspiring Solopreneur, the podcast for those just taking the bold step or even just thinking about taking that step into the world of solo entrepreneurship. My name is Carly Ries and my cohost Joe Rando and I are your guides navigating this crazy but awesome journey as a company of one. We take pride in being part of LifeStarr, a digital hub dedicated to all aspects of solopreneurship that has empowered and educated countless solopreneurs looking to build a business that resonates with their life's ambitions. We help people work to live, not live to work. And if you're looking for a get rich quick scheme, this is not the show for you.

So if you're eager to gain valuable insights from industry experts on running a business the right way the first time around or want to learn from the missteps of solopreneurs who paved the way before you, then stick around. We've got your back because flying solo in business doesn't mean you're alone.

Carly Ries: So Sydney, Joe and I were joking offline with you about, oh gosh, why would we ever wanna have an Instagram expert on this show because we're so good at it. The reality is we're really bad at it. And so when you came across my inbox, I was like, oh my goodness. Yes. So, listeners, this is for you, but this is also for Joe and I because we have some work to do when it comes to Instagram strategy.

So anyway, Sydney, welcome to the show. We have so many questions for you.

Sydney O'Brien: I'm so excited to answer all of them.

Carly Ries: Well, before we dive in, we have this new thing that we're doing with guests that we think is just really fun to do to get to know each other. So we wanna ask you, what is the wildest thing that's happened to you as a solopreneur?

Sydney O'Brien: Okay. It was actually like how I became a solopreneur because I started my business when my kids were six months and two and four years old while my husband was deployed and I was in a new city. He's in the air force and I didn't know anyone. And for some reason, I decided, you know what? This is a good time to start a business.

Joe Rando: Yeah. Brilliant.

Sydney O'Brien: Perfect timing.

Joe Rando: Years ago, we had kids like that, you know, close together and it's nuts. It's nuts. That third one just like sent everything toppling off the cliff. and I was there. I was around, and it was anyway, you are crazy. Serious. You know, certifiable.

Carly Ries: Yeah. But it's a star and a rock star too.

Joe Rando: Yes. It worked.

Carly Ries: It worked. It did.

Sydney O'Brien: It worked out well in the end.

Carly Ries: It did. And that's why we have you on today. So we have so many questions, I'm just gonna kinda do the questions that I personally need to know, and I think a lot of our listeners can relate. How can solopreneurs better identify and speak directly to their dream client through all the social content and actually reach who you need to reach on Instagram?

Sydney O'Brien: The best way to do that is by talking to your people. Like first knowing exactly who that is. niching way down and then talking to them and kind of regurgitating their words back to them in your messaging. Because the thing you really wanna share that's gonna grab attention is those anxious thoughts that your ideal client or customer has that's keeping them up at 11PM when they so badly wanna go to sleep but they're worrying about this one thing. That's what you wanna talk about in your content.

Because they'll be like, oh my gosh, that's me. I know this person can help me with that.

Carly Ries: Yeah. good point. And it's funny because is there any like targeting? Do hashtags still work? Is there any targeting that you need to do to reach these people?

Because I'm thinking Instagram, you have access to the entire world. How do you make sure your audience, even if you understand them, how do you make sure they're the ones that see it?

Joe Rando: Right. Yeah. Good question.

Sydney O'Brien: So hashtags don't really work like that anymore. They used to which was really nice. But Instagram is moving more towards SEO, search engine optimization. So it's more about finding long tail keywords.

Like for me, I could use Instagram strategy, like digital marketing tips, things like that. And also outreach is really helpful if you can do some outbound engagement with accounts that are complimentary to your business. So because I'm an Instagram strategist, I could find an email marketing person and comment on their account and their followers are also in my ideal audience. So they'll see my content as well.

Carly Ries: Oh, that's smart. See, it's things like that where that makes so much sense and that's so logical. But for some reason when I get down to actually put a post in place, it's like, oh, all that goes out the window. Hey, question though. Quick question on that. So when you do go and you post on that email marketing person's content, what do you say, what are the rules,

Joe Rando: like, for kind of engaging people in a way that they're gonna notice you, but not being overly salesy or, you know, not looking like that kind of sleazebag that's coming in and trying to, just sell everybody.

Sydney O'Brien: Right. Yeah. That's always a concern. I always try to, add value to the post without, taking anything away from it. So if someone's talking about one I did recently just the other day was an Instagram marketer shared why she doesn't like email templates because it takes a lot of your voice away.

I was like, I'm the same way with Instagram. I love the idea of a template because it makes life easier but it takes so much of your voice away and that's what people resonate with. So I was like adding to the content but not dismissing anything she was saying and not being super over promotional.

Joe Rando: Yep.

Carly Ries: how do you get people to engage and comment and everything?

so I actually stopped posting on my personal account back in 2020 because I found that if I didn't get a certain amount of engagement, it would affect my day. And I'd be bummed out. And then it was like, people weren't commenting on pictures of my kids. And like, that's the cutest kid ever.

And then it was just like, that's ridiculous. My day should not be dictated by this. So I just stopped even trying to get engagement and then just stopped posting. But for people that need that engagement for businesses, how do you foster continuous conversations, DMs, comments, the works?

Sydney O'Brien: So it's partly the two biggest mistakes that I see with this for people wanting engagement but not getting it is like specifically asking for it. specifically being like, hey, comment on this specific topic or what are your thoughts about like this very specific thing. And also again, outbound engagement, even just replying to people's stories, the more you give out to people in engagement, the more you're gonna get it back. And it also helps nurture followers and potential leads and things as well.

Carly Ries: Okay. So I keep seeing the comments and everything. In terms of content mix, reels, stories, posts, like, what is working? What tends to perform the best for solopreneurs, obviously, who are talking to you, anybody for that matter?

Sydney O'Brien: Sure. It really kind of depends on your audience. Like right now, I'm seeing a lot more reach and engagement on carousels when a couple months ago for me, it was reels. So there's like a shift there. But I have clients who are still their reels get so much more reach and engagement than their carousels do.

So having a good mix of both and then stories are also really great for just kind of connecting with your audience. You can get some good engagement there just showing behind the scenes, like what you're doing with your day, what you're working on, that kind of stuff. But if you're really not sure, I would always suggest checking your insights. You can filter them by seeing what gets the most reach, what gets the most engagement, and just focus on those so you're not wasting your time on things that you know aren't gonna work.

Carly Ries: When I feel like there's so much pressure to how I get get the best template to use, like for a person that's never created a reel, it's really intimidating. Do you have an editing software or anything to make it really really basic for people that wanna have an impactful video but are just like like CapCut, like what tell me what to do.

Carly Ries: Yeah. Help me. Help me.

Sydney O'Brien: CapCut is definitely one of the best ones because it is so easy to use and it's free. And there are a lot of templates in there which make it a whole lot easier so you don't have to do any of the editing. You just upload a couple clips and it'll do all the editing and formatting and stuff for you. Instagram also came out with their own editing app called edits, which is nice because you can push it directly to Instagram from the app. And it'll also give you updates on insights for your reels.

It'll send you notifications like, this reel is doing this percent better and reach your engagement, which is interesting to see. But I do like that CapCut has templates and edits doesn't. So definitely points for CapCut there.

Joe Rando: Isn't CapCut owned by TikTok?

Sydney O'Brien: It is, yeah.

Joe Rando: So one of things that made me nervous about it was when they were talking about banning TikTok, you would have lost your editing app, right?

Sydney O'Brien: Yeah.

Joe Rando: I guess that's not really a big deal now. But boy, I was looking at it and I went, Nah, I'm gonna use Premiere.

Carly Ries: Yeah.

Carly Ries: Well, so let's say there's a person listening and they're like, okay, I'm gonna check out CapCut. It's free or edits just to try to make it look a little bit better. But still there's a learning curve. It could take time. So we always recommend that people batch their content and then schedule it out so that they're not everyday trying to figure out a new thing to do.

Sydney O'Brien: Absolutely.

Carly Ries: How can a person do that with Instagram and make it quality so that they don't get burned out?

Sydney O'Brien: I always recommend batching because for the same reasons. It kind of depends though. So the way I batch, how I batch content for my clients and how I teach other people to batch is you plan out your whole marketing plan for a month or so, however long you typically do it. And then week by week go in and create content just because trends are always changing. How people consume content is different.

You don't want to batch too much and then have it become not relevant even though you're putting time and effort into it. So have that full marketing plan so you have the buyer's journey outlined with your content. So you can still lead people to buy by the end of it, but also kind of break it down. It's also more manageable too if you don't have a whole bunch of time to just sit down and create, like, an entire month's worth of content.

Joe Rando: Can I ask a dumb question?

Sydney O'Brien: Of course.

Joe Rando: That's My specialty when it comes to anything related to social media. So you just said to have your buyer's journey mapped out. And I know what a buyer's journey is. I think most of our listeners have the concept. But how does that work in the context of social media where you're posting and people are seeing it from all different aspects?

Are you just resonating with this particular post resonates with this person at this particular point in your buyer's journey? Is that is that how it works?

Sydney O'Brien: Yeah. So the way I teach it, I've created five steps to sales on Instagram like framework. And it's growth, so you have the right followers, engagement, connection, trust, and then promotion. And I will do a couple of posts for each step so that it's getting seen by people and then it leads up to a launch or a sale or whatever it is that I'm promoting. So yeah, it is hard to kind of meet everyone where they're at. I just focus on my personal business plan and go around that. Okay. So you've got a group of people that see the first one, get brought along. Some people are seeing it in the middle and maybe going, I don't get it. Or, you know okay. Good. that just clears up so much. Thank you.

Carly Ries: Well, so we were talking about batching all of your content and everything going in on a weekly basis, but user generated content or people creating the content for you that you could share. I mean, how can people encourage that so not all the pressure is on them to keep creating content?

Sydney O'Brien: Mhmm. That can be a little tricky. The best way to do it is kind of incentivize it honestly. make it clear like kind of they get something out of it as well. I ran a challenge a little while ago and I got a bunch because I had a bingo card for it and people could be entered to win a prize.

And part of it was creating content and tagging me in it as like a collaborator. So it would show up on my feed as well about them interacting with the challenge, showing their insights and things like that. So I got reach and visibility for it for me, but they also get prizes for them.

Carly Ries: Alright. I'm, taking mental notes on all of this.

Joe Rando: Well, it obviously depends on your audience. Right?

Sydney O'Brien: Very true.

Joe Rando: If you had an audience of attorneys, you know, high powered attorneys, they probably wouldn't be going for the bingo card contest. But with the right group of people, it's a brilliant idea.

Sydney O'Brien: Yeah. Yeah. It's definitely gonna depend on the industry.

Carly Ries: For people that have a bunch of content and they're like, yeah, I have all of this, but they aren't really seeing a lot of results, is there a way to do a content on it on Instagram and how should people go about that to identify gaps and what's working and what's not?

Sydney O'Brien: For sure. You can look at the benchmark rates for insights like if you're not getting, I think it's a 3% growth for your account for a month that's like below average. So you can focus on trying to get more followers. A great way to do that right now is if you have the trial reels feature. That's a really good way to get more followers because Instagram automatically shows your content to people that don't already follow you but are interested in the topics you post about.

So you could do more of those. If your account gets around 5% engagement, that's average. So it's actually a lot less than people would expect. If you are getting DMs for sales or getting clicks to your website, you're doing better than average. The conversion rate for most Instagram posts for promotional content is 2%.

Carly Ries: It's funny because I as a marketer, those numbers sound pretty normal, but I can imagine if there's just random solopreneur and it's like, what? Those are the numbers?

Joe Rando: Yeah. all that work and all that post and all that.

Carly Ries: Yeah. Exactly. Well, so it can seem like a lot for people. They're running their business, and so they have to worry about other areas, areas of marketing, but their operations, processes, everything. So when should it would you think a solopreneur should consider hiring a freelancer to help with this or a contractor?

Or even partnering with an agency instead of taking it all on themselves?

Sydney O'Brien: I think a lot of it comes down to like most decisions budget and time. if you just don't have the time, it's definitely worth looking into some kind of outsourcing, whether it's a membership or one on one work or an agency. But also your budget is obviously going to influence that as well. The biggest thing I would say if you're going to outsource completely is make sure you have a one on one call or conversation with someone first to make sure they're a good fit for you.

Carly Ries: And what should they be looking for? Like you say good fit, but is it personality? Do they understand your brand? are there any red flags that people should look out for? Because I've heard time and time again that people are like, oh, I had a great discovery call with this agency and then FWOP.

They seem like a great contractor to work with, FWOP. And that they just, they're wasting so much money.

Sydney O'Brien: Yeah. I would make sure they understand your brand and your values because the way social media works is your messaging has to be spot on and it has to be in your voice for it to hit home with your audience. So the person you work with really needs to understand that, and I would also ask to see like a portfolio and things to make sure that they're doing that for other clients as well.

Carly Ries: Is it common to speak to current clients? to be like, can I talk to one of the people you're currently working with? Or does that not really happen?

Sydney O'Brien: It hasn't really happened in my experience, but I also like when people have a call with me, I give them a packet of information. It has reviews and insights and information from other clients. So they do have all that information. But if that's not provided to you and you're looking to hire someone, I would certainly ask.

Carly Ries: Okay. Yeah. Because like you said, there's just a lot to think of.

Sydney O'Brien: Yeah. Actually That's a big decision.

Carly Ries: When there's, like, done for you packages and all of that stuff. Joe, I think those are a lot of my questions that I had that I just needed to get this out there. Do you have any that I've missed?

Joe Rando: Well, no. I think just to expand on what you said, I think what is implied in this last exchange was that it really has to be you that's coming across. Now whether it's actually you writing the words in order that's gotta be coming from you somehow. So is there any thoughts you have on how if you're having someone help you, how do you kind of convey you to them in a way that lets them authentically represent you when they're doing this work? Or is there some kind of back and forth that should go on in order to make sure that it's all on target?

Sydney O'Brien: So normally, there's a discovery call and a whole bunch of at least when people hire me, there's like an intake form where I look over, they answer questions about their values, their mission, all of this stuff. I'll do deep dives into their website to look at their copy there. I'll have them write other paragraphs about what they do just off the cuff and have a conversation with them to hear what they talk like. It takes a little while to get their voice and messaging right, but it is just such an important part.

It's definitely worth the forms and the phone calls to get there.

Joe Rando: How is your Boston?

Sydney O'Brien: My Boston?

Joe Rando: Yeah. if you're channeling me, I grew up outside of Boston. So people are wicked smart.

Sydney O'Brien: It's Yeah. I'm from New Hampshire, so it's not too bad.

Joe Rando: You've got that. You don't sound like New Hampshire.

Sydney O'Brien: No. because my husband's in the air force, we move around a lot. yeah. We hear all the all the accents.

Carly Ries: A lot of us, they can master it.

Well, it sounds like you've helped so many people people find success on Instagram. So we ask all of our guests this question, what is your favorite quote about success?

Sydney O'Brien: I really like this one that Serena Williams said. She said, success is doing the things most people don't have consistency for, which I feel like really applies to being a solopreneur because so much of it is just being constant and being consistent so you can get those results that you want.

Carly Ries: Thanks for tying it back to the audience. Much appreciate it. Well, Sydney, this has been great. Thank you so much for answering all of our questions. If people wanna learn more about you, where can they find you?

Sydney O'Brien: Absolutely. My Instagram is a great place. My handle is at socially.yours.strategist. I have a podcast called mompreneur mastery. I also have a free content planning, five day challenge to help you plan a month of content in five days called Plan it Post it Profit.

Carly Ries: All of that will be included in the show notes. And thank you so much for coming on today.

Sydney O'Brien: Thank you so much for having me.

Carly Ries: Yeah. And listeners, thank you so much for tuning in. As always, please leave that five star review. Subscribe to this show on your favorite podcast platform including YouTube. Share this episode with a friend, and we will see you next time on The Aspiring Solopreneur.

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