August can often feel like a strange limbo for solopreneurs and independent experts – a mix between wanting to relax and feeling pressured about what lies ahead in September. In this episode, Anna Lundberg shares practical strategies to help you enjoy the summer season, set realistic boundaries, and ensure you’re well-positioned both emotionally and financially for a strong return in the final quarter of the year. Whether you’re feeling guilty about slowing down or anxious about next month’s pipeline, this is the episode for you.

Key moments:

[00:00] The August dilemma for freelancers and business owners

[03:04] Why it’s normal to feel tension (family, work, and guilt)

[05:30] Identifying your ‘season’ (recharge, reboot, reconnect, realise)

[07:56] Setting intentions for how you want September to feel

[09:32] Translating intentions into practical actions and priorities

[10:28] Live vs. asynchronous activities: how to work around summer

[12:34] Crafting boundaries and outlining your non-negotiables

[13:30] Quick wins: cashflow and creative summer offers

[15:43] Sowing the seeds for Q4 sales (it starts now!)

[18:05] The three key sales pipeline metrics

[20:12] Final reflections and moving away from “all or nothing” thinking

[21:33] Invitation: Connect with Anna for strategy support

Resources mentioned:

• Anna’s Summer Strategy Session (Free 45-minute workshop): email podcast@onestepoutside.com or message Anna on Instagram or LinkedIn to request access, including the workbook.
• Power Hours and Voice Note Coaching: email podcast@onestepoutside.com or message Anna on Instagram or LinkedIn to request access, including the workbook.
• Business Accelerator Programme: Next cohort opens in September for an October start. Learn more or register your interest at: onestepoutside.com/accelerate

Summer Business Strategy

This episode is for you if August feels kind of messy, you want to slow down. But you’re also aware that September sales unfortunately don’t start in September. You need to get going now. Maybe you’re juggling family, feeling guilty about switching off, or just tired of winging it through these in betweeny weeks. If you want a simple, focused way to enjoy the season and set yourself up for a strong September, this one’s for you. Welcome to Reimagining Success, the podcast that helps you build a profitable business as an independent expert, one that works for you and your lifestyle.

I’m your host, Anna Lundberg, former corporate insider turned business mentor, executive coach and mum of two. Whether you’re a solopreneur, a coach, speaker, consultant, I’m here to guide you in creating a business that gives you freedom, flexibility and the fulfilment you’re looking for, ready to redefine success and build a business that you love. Let’s get started. Okay, so we’re into the first week of August, and as a solopreneur, as an independent freelancer, fractional, whatever we call ourselves, it can feel like a pretty awkward month because a lot of us are craving a real break here in the Northern Hemisphere. It’s beautifully sunny, but we’re also possibly quietly panicking that the year is slipping away. We’re more than halfway through, beyond halfway through, in fact, into August, month eight. And I’ve spoken to quite a few experts recently in my own programme as well as in other programmes I’ve been part of and communities. And there’s a.

There’s a lot of anxiety is a strong word, but certainly nervousness around, you know, oh, I don’t have a pipeline for September and so on. So especially when we’re starting out, but perhaps even more so when we’re further along and we have, you know, more expenses and higher expectations of the salary that we’re bringing in, the income we’re bringing in, that can put a lot of pressure on us. So as much as we want to set the intention, like, oh, I’m going to take the whole summer off for my own sake, for the kids, whatever, there is that kind of spectre hanging over us of, oh, gosh, we haven’t earned a lot of money, we need to earn more money. And this is now a couple of months completely away, because, again, in the Northern Hemisphere, as I keep saying, because I know I’ve got listeners in Australia, New Zealand and South Africa and all sorts of Places. So give me a shout out if. Yeah, if you’re in somewhere very exciting that isn’t going through this period. But you can also listen to this episode in your equivalent, which might be January, let’s say in the southern hemisphere, but summer, July, August, for me, as a parent of two school aged children, it is now effectively almost two months off with childcare, with camps and so on. And in between, whether or not we have children of school age or children at all, the, the reality is that a lot of offices will shut down, the stakeholders are out, decision makers aren’t going to be able to prove your projects and things.

And it is a period where as a society we tend to kind of slow things down. Okay, so this tension is normal between, oh, I’ve got these ambitions and I want to grow and I want to and need to bring in that money and those skills, sales, but we need to be realistic and compassionate with ourselves both that the market is such that there won’t be huge opportunities depending on what industry in you’re in. If you’re in the wedding industry, it’s probably too late now, but you’re probably very, very busy and not listening to my podcast. If you’re the Oasis tour manager, you’re probably busy too, but for most of us it slows down. Okay, so there is this tension, there’s the family holidays, maybe slower client responses and possibly an underlying guilt. Should I be doing more? Should I just switch off? So I want to normalise this first of all and then talk through a few things about how we can reframe this both to set the intention because it’s not too late for the summer and to set the tone for September sales and our year end goals. So for me, always, in fact, it’s never about hustling harder, right. It’s about getting intentional and really understanding.

I’ve been talking a lot about seasons recently and, and thinking in this context of okay, is it for you a season of recharging because you’ve been really working, you know, grinding, hustling, whatever word you want to use, you’re feeling it, you do need a break and you have, have the finances to support you at least to be able to take that time off because otherwise that break can be more stressful rather than more relaxing. And, and certainly if you, yeah, if you have had a great sales period. The ideal of course, is that we front loaded the year so we’ve got lots of money in the bank and now we can just enjoy the time off. Now when I say that recharge I love still, and my partner, who I don’t think listens to this episode or this podcast, rather, has never loved it when I do that on holiday, but I do, which is I get out my iPad or pen and paper and I ideate and I brainstorm and I strategize and that’s just my favourite thing to do. So I’m, you know, I’m really passionate about that kind of thing, but I don’t want to do live calls and things that, for me is actually energising on holiday, whereas, you know, having to fit calls that are booked in and then people cancel the calls at last minute and then you feel resentful and so. And that’s the energy that I don’t want. So maybe you want to recharge over the summer. Maybe you’re actually at a kind of pivotal moment where you need to reboot, recalibrate your whole business model or at least take a step back, look at the strategy again.

For me, that’s a great time to do that over the summer and to really take that step back and look at the bigger picture. Because the rest of the year we tend to be sort of in that kind of go, go, go mode and we’re busy delivering client projects or trying to get clients, and we don’t always have that time to take a step back and look at the bigger picture. Reconnecting just because, you know, some of us are out of the office, and so it doesn’t mean that you can’t have chats with people. Depending on what industry you work with, depending on your time as well, this may certainly be a time when you can, you know, certainly send LinkedIn requests, follow up on emails, respond outbound messages, just understand that there will be a slower response, potentially. But some people might very well have more downtime and therefore be more willing to talk to you over the summer. So that’s something to consider as well. So, you know, for me, little things like responding to, you know, the hundred LinkedIn connection requests I have that I haven’t looked at, but I want to do that. I’ve already deleted the totally irrelevant ones, but I need to do this with care now, and, you know, giving a little nudge to some people, saying, hey, you know, just to let you know, I’ll be off now, but, you know, reconnecting in September, let’s get a call in, or something like that.

So reconnecting can be important, or maybe you’re in the fortunate and exciting place where you actually want to realise a particular Project. Right. So you might want to finish your book, plan your TED Talk, launch your. Or not launch perhaps, but you know, map out the modules of your group programme or something like that. So are you recharging, rebooting, reconnecting, realising, or maybe there’s another that you want to do, resetting, who knows? And if it’s all four that resonate, then I would give a gentle warning to say, I suggest that you identify the big priority. Obviously, again, if the pressure is there with the business and you’re passionate and excited about doing certain things, we might want to balance the, the recharge with one of the other R’s because we all need to recharge, I’m sure. But just be careful with over promising and setting a really muddied intention because that’s going to be really hard to then make decisions. So a key question, and you can pause and listen and reflect on this or come back to this later, but the question is, what do you actually want September to feel like when you’re back at your desk? So that’s a feeling, but also what do you want to already have in motion? What needs to be true for you to feel like, oh yeah, okay, I really did.

I use the summer to my best ability. I recharged, I planned this thing, am I connected to people, whatever that was. So, you know, a general sense of, okay, how would I want September to feel? I want to come back energised and maybe I haven’t done all the things, but I’m ready to go in September, then I’m going to lean in, for example. Okay, so let’s break this down into more practical terms. That’s sort of a general intention, but let’s get really, really clear. As I said, what’s one thing? Let’s say if done by early September, for me it’s end September because my son has a very gentle settling in schedule at school. But early mid September, whenever you’re back to work, as it were, what one thing would make you really feel proud and calm heading into the final quarter of the year? Because we’ve got four very important months again in the northern hemisphere, at least in our countries, we have Christmas coming up. So arguably it’s maybe three months.

So quickly we see how the months and weeks slip away. So maybe it’s finishing a project, filling September calls, filling a programme, or again it might be having just completely relaxed and that’s the most important thing. So that’s the first question. What one thing by early September needs to be kicked off in Motion finished for you to feel really proud, satisfied and calm heading into Q4. Okay, and again, you might want to pause this. You can listen to this later. And in fact, I did a whole workshop on this. So if you do want the full recording with a bit more detail, it’s 45 minutes.

Then let’s say message me, I’m Anna Se Lundberg on Instagram. You can connect with me on LinkedIn or, or email@podcastonestepoutside.com and just let me know that you want the summer strategy training. There’s a workbook as well. And so based on that overall goal, you’re choosing three, four, max. Five, I’d say priority actions and importantly, categorising them whether they’re live actions or asynchronous actions, meaning live is okay calls events, networking, you know, having actual conversations where two of you or more need to be together. Running a workshop, for example. Again, I’m not doing that over the summer because that doesn’t work with my family setup, even if, you know, the kids are at camp or something. I feel like that just puts pressure on me and actually love having those days as sort of bonus times to work on my book or work on something that I don’t usually make so much time for.

So live needs to be, you know, together, possibly virtually, possibly in real life, but one to one, one to many happening at the same time, asynchronous. On the other hand, obviously anything like creating content, nurture sequences on emails, reviewing your offers, any kind of strategy. Also, I would say all this messaging, responding to emails, following up with warm leads, LinkedIn messages and so on, right? That can all happen. I’m looking at pitching myself to a few conferences and podcasts. And even if again, it might be slower on the response from the other end, I now have the time to spend a bit more, you know, put a bit more care into that now versus the week when I’m doing all the other things. Okay, so you want to move the needle, but. But be really clear on what those handful of things are in the sort of small focus sprints and be clear on what you’ve got that you can do asynchronously when you’ve got half an hour here or, you know, maybe an evening, if you are happy to do that, you might do sometimes I do some Instagram content or something, you know, like that. That feels kind of fun.

Or brainstorming with ChatGPT or whatever. That can be done whenever you want to. Whereas again, live is much more, oh, I need to be there at my desk or out and about, dressed up, whatever. Okay, so we’ve got our clear intention, our end of summer goal, we’ve got our three to five priority actions. Are they live, are they async? And then I want you to be super clear on what your boundaries are. And a term I often use is your non negotiables. Okay, so is it that you know, you’re not, not going to take any calls during XYZ dates or days, you’re not going to work on Fridays after a certain time? Is it certain events or days or times that you want to definitely be present? You know, what are those family times or health priorities you want to make sure that doesn’t slip over the summer? Maybe going to bed early, maybe putting, you know, nutrition or drinking or water, whatever it is. And what are your non negotiables that you’re putting in place? Still trying to get those 10,000 steps.

Or having the early bedtime, whatever that looks like. And think about your boundaries as you know, actually the. It’s not saying no to people, it’s respecting yourself and them to prevent you from feeling guilty or resentful further down the line. And it really is part of your business strategy. Right. Having these boundaries is going to help you compartmentalise when you are working, when you’re not, and really help you feel like you’re present wherever you are. And that for me is so crucial. I don’t want to have the kids banging on the door when I’m trying to do something on my computer.

It puts a lot of pressure on me. They’re unhappy, I’m unhappy, it’s no good for anybody. And then I suppose just very tangibly thinking about some quick wins in terms of cash flow. Right. So really obvious ones are chasing unpaid invoices. Okay. My aunt. Hey, hey.

Beat that. Would always say prioritise money in. Okay. So any unpaid invoices, anything that you’re owed, please prioritise that. Okay. It’s not being pushy. You’ve delivered a service and that needs to be paid. In the uk, you know, there’s interest we can charge when things are delayed and so on, but that’s really important.

And then of course there are some things maybe now in August, not so much. What I tried to do last month in July was, you know, I offered some one off power hours. I also got a bit creative and I’ve offered asynchronous voice note support for the summer. So voice note coaching again, if you’re interested in this, it’s still available for the summer. So again, you can connect with me on LinkedIn, Instagram or email@podcastonestepalside.com and I’ll get back to you. But, you know, getting creative with little things that you can still deliver. If you have obviously some kind of ebook resource course, workshop recording or something, why not ping your list and say, hey, I’ve got this thing, 30 pounds, whatever. You know, it’s not making millions right now, but it’s finding ways.

If you really are feeling nervous about cash flow, let’s not just pause and avoid this and wait until September, because two months of no cash flow is not going to make you feel better, right? So really think about again, chasing on paid invoices for work that’s already delivered, locking in calls and meetings and next steps for projects that are kind of on the go, offering things like one off power hours or voice note kind of things. Obviously there’s no such thing as passive, but it could be that you have some resource that you can sell. Also possibly securing deposits for September, October work. Right, so now perhaps nothing will happen. I’ve had a couple of August the last few years when I’ve had big keynotes and off sites planned in August, which caused a lot of stress, but was quite nice for the cash flow at least coming, coming in to kick things off before even September started. But really, can you. If people are saying, oh yeah, let’s talk after the summer, great, let’s get call booked in, right, Because September will quickly fill up and then it won’t be October, November and before you know it, you know, more months have passed. So that’s quick cash flow without panic.

But we’re also wanting to sow the seeds for the final quarter, right. September sales don’t start in September. I was telling this to a client the other day who’s launching a group programme and she started already now in July, in fact, to sow the seeds because people don’t see a post and go, oh, yes, perfect, yes. I’ll contact this person I’ve never met and I’ll message them and I’ll give them all my money. It’s happy days. It does happen. It certainly happened a couple of times early on in my life and it’s my life early on in my business. At least it’s not so common.

So really, already, for me, the worst thing that can happen is like a week before the accelerator closes or something. There’s, oh, I’ve got no one, I’ve not talked to anyone and I have to Kind of be really pushy. Whereas if, you know, I have this cadence now of I know I’m opening it quarterly. I’ve got a list of people who last time said, oh, it’s too early. But next time I’m connected with people on LinkedIn, you know, we can start having genuinely no pressure conversations because there is no pressure. I’m just trying to get to know them and if I can support them, happy to do that. You know, that just takes the pressure off. So think of sort of low effort, high impact things you can do again.

Outreach to warm leads. Oh, shall we book a September catch up to hear what you’re up to? And you know, I’ve got this new thing that might be interesting. Should we chat about that? Obviously, I say obviously I’m not going to. And you can you say you heard it here first. I’m not going to be scheduling, as I often do, daily posts on LinkedIn, Instagram, and so I’m really dialling that back for the summer. But a couple of a handful of valuable posts from your side, you know, simple emails, newsletter if you have one, to keep your visibility ticking over. Obviously you can schedule that before so you don’t have to do it live or. And that’s a whole other topic.

But if you have sort of a library of content you can draw on that you can repurpose and so on. And then, you know, something I shared in the workshop and again, if you want to watch that, just ping me a Note podcast@onestepoutside.com for the summer strategy session. It’s free 45 minutes and I just did a little funnel where the three metrics that you really need to be looking at are, okay, kind of warm conversations that you’re having. Proposals and sales confirmed. Now, conversations is not just connecting with someone on LinkedIn, it’s actually having a bit of back and forth, possibly having a call, you know, really chatting. This is a qualified lead, someone who would be perfect for my accelerator. And I’m going to propose something to them. The second one is proposals or offers made.

I’m not saying that you have to send a 12 page PowerPoint deck, which you certainly shouldn’t do, or word or whatever. And what I mean is that you have made an offer. So if I’ve said to you, oh great, I think you’d be a really good fit for the accelerator. It costs this much. You can buy up front or you can pay quarterly. Are you in kind of thing? Right. So I’ve said that to you on a phone Call, I’ve sent the email to you. That is an offer made and then the sale confirmed is not when you say yes, great, because that can change.

It is when the money is actually they’ve clicked on the pay button and you know, or you’ve sent the invoice or whatever. In the case of a corporate client. So those are the three things to think about. So not to panic, but just to look at that. Okay, if I don’t have, and that’s the big number, I think the proposals, if I’ve got seven or eight different things that I’ve picked to people and you know, a few people interested in this, one to one, coaching workshops, whatever, then I’m feeling relatively comfortable. Even if unfortunately, sometimes none of them work out, or at least a handful of them do. There’s stuff happening. If that column or row is empty, there’s no proposals out.

That means that, you know, the next few months are not going to be looking particularly good because again, we’re not going to get a lot of spontaneous sudden sales. So again, no panic, but it means let’s start sooner rather than later to have those conversations, which gives you a longer run up to nurturing, qualifying, warming them up to possibly making a proposal and then ultimately, hopefully getting sales. So that’s just something to think about. Not to be mercenary and talk about money, but that is the sort of that thing that’s hanging over us. Right? So I leave you those reflective questions. What’s your clear goal for the end of summer? What three to five actions will help you get you there? Where might you want to set boundaries to make this work? And what are those non negotiables? And hey, why not say one simple thing you can do this week to seed Q4 sales? Whether it’s, you know, reaching out to past clients or following up with people you had conversations with who said, oh, maybe or not. Now there are some things we can do to nudge that long. So I think the main message is August doesn’t need to be an all or nothing month.

It’s up to you if you want to go fully, recharge, reset, realise whatever you want to do, but be intentional about it. And yeah, a few small intentional actions that you take now and over the summer can really change how September feels completely. Whether it’s doing things that have been on your list for a long time, you just haven’t taken the time to do it, haven’t made the time, or it’s something that you just realise now would shift things, whatever that is, that can make all the difference for when you come back. And it’s not to put lots of pressure on you, but let’s not go to either of the extremes. Let’s not completely avoid it and go, ah, no point now, I’ll deal with it in September. And likewise, let’s not put super amounts of pressure on ourselves and be like, oh, I’ve got to do everything now over the summer, right, because that will just disappoint us and or burn us out. If you do want to help mepm this out again, I’ve got the summer strategy session so let me know about that. I am still offering a handful of power hours and that voice coaching voice note coaching.

So let me know about that. And of course we do have our accelerator. The next cohort opens in September for October, so there’ll be more about that later. But just sowing the seed so that you think about that over the summer as well. Hope that was helpful. Have a lovely summer. But I will be back next week with another episode because these are all pre scheduled before the summer and I hope it’s useful. Bye for now.

If this episode has you thinking that something needs to shift, whether that’s streamlining how you work, redesigning your offers, or finally building the business that you actually wanted when you started, let’s talk about what’s next for you. We can look at where you are, what you want these next few months and years to feel like, and whether one one support or the business accelerator would be the best fit. Just book a call at onestepoutside.com/call. It’s a simple conversation to explore what would make the biggest difference for you right now. That’s onestepoutside.com/call.

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