Totally Bossing It · 2025-04-10 · 6 min
Key moments - from our scoring
Substance score
11 / 100
Five dimensions, 20 points each
Peak tax season from April to June creates what Natalie Lennon, founder of Two Sides accounting firm and Two Sides Academy, calls 'the washing machine' - a period where accountants must simultaneously manage quarter-end processing, FBT year-end requirements, tax planning deadlines, and last-minute client submissions before May 15. Lennon reflects on how her 100% remote firm, despite having procedures, checklists, and trained teams in place, still experiences stress during this compressed period. She shares strategies her firm uses to manage scope, including setting firm deadlines requiring client information by end-April and warning clients they may miss tax deadlines if materials arrive late. Lennon normalizes the burnout many accounting firm operators experience during these months - deprioritizing gym, nutrition, and content creation - while emphasizing this is a temporary annual pattern, not a permanent state of business dysfunction. She also addresses why podcast production drops during this period and draws parallels to business resilience lessons learned during COVID. For B2B accounting operators, this episode validates common seasonal stress patterns and reinforces the importance of setting client boundaries and maintaining perspective.
May 15 is the deadline for lodging individual tax returns in Australia; accountants must collect client information and complete returns by this date, creating the compressed April-to-June rush period.
Two Sides sends communications warning that information must arrive by end-April or the firm may not be able to complete returns on time, and for prepaid clients, explicitly states the deadline or refusal to commit to meeting lodgement deadlines.
Growth means more clients to fit into the same compressed period, client expectations for on-time delivery persist regardless of preparation, and the volume of simultaneous deadlines (FBT, tax planning, individual returns) compounds naturally, regardless of process maturity.
No - it's a normal seasonal pattern that resolves in July when the rush passes, unlike year-round dysfunction; the key is recognizing it as temporary and maintaining boundaries rather than treating it as chronic operational failure.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode is almost entirely filler - a personal check-in explaining why the podcast is going quiet during tax season. The only remotely tactical point (send clients a deadline warning email) is obvious to any practitioner, and it is buried under extended rambling about COVID PTSD, gym attendance, and wine on weeknights.
I just wanted to hop on say hi and you know explain why the podcast will drop off a bit uh from now until july
it's a similar thing, right? It's tax season. It's when we're in the thick of it. It's crappy. We don't like it. We hate life.
There is no original thinking whatsoever. The 'washing machine' metaphor is a mildly colourful label for an entirely clichéd observation (busy season is stressful). Every claim - it passes quickly, we care about clients, self-care matters - is a platitude circulating in every accounting community.
it's a small period of time in the financial year. And yes, it happens every year. We should be more well-prepared
we generally really care about our clients and making sure that they're looked after
There is no guest at all - the episode is a solo, unstructured monologue. The host has legitimate credentials (chartered accountant, former partner, firm founder) but demonstrates none of that expertise in this episode; it reads as a personal diary entry rather than practitioner insight.
I'm Natalie Lennon. I'm the founder and director of Two Sides, an 100% remote accounting and bookkeeping firm
I became a partner at 28 and five years later, I sold my 40% share and started Two Sides
The only concrete details are the May 15 lodgement deadline and the end-of-April client-information cutoff - both well-known statutory facts for Australian tax agents, not original data. No metrics, no firm-specific outcomes, no named tools or processes are shared.
trying to get every everyone every old bugger who's left their tax returns to the last minute to meet the May 15 deadline
we did send out some emails the other day basically saying if we don't have your tax return information by the end of April we may not actually be able to do your tax return for you this year
There is no guest, no interviewing, no questions, and no dialogue of any kind. The episode is an unstructured apologetic monologue with no arc, no follow-ups, and no productive tension - purely a note to listeners that content is being paused.
I guess I just wanted to hop on say hi and you know explain why the podcast will drop off a bit
that's enough rambling from me
Computed from the transcript - who did the talking, and the words that came up most.
In this short but important update, I’m diving into what I call “the washing machine” - that whirlwind period from April to June where tax season kicks into overdrive. It’s a wild ride of deadlines, long days , and all the moving pieces that come with supporting clients through their busiest time of year. Thanks for your support and I’ll see you on the other side - post-spin cycle . - - - - - Follow me on Tiktok . Follow me on Instagram .
Transcribed and scored by The B2B Podcast Index.
Welcome to season three of Totally Bossing It, the podcast. This season is for accountants who want to totally boss it in their accounting firms. I'm Natalie Lennon. I'm the founder and director of Two Sides, an 100% remote accounting and bookkeeping firm in Sydney's south.
I'm also the founder and director of Two Sides Academy, an education business where I'm on a mission to educate accountants and bookkeepers to build their brand and businesses to enable them to live their best lives and to work less. I'm a chartered accountant and registered tax agent with over 20 years experience working with and in various small, medium and multinational businesses. My mantra is to work smarter, not harder through the application of streamlined processes and smart technology.
I became a partner at 28 and five years later, I sold my 40% share and started Two Sides. I was very scared and thought WTF have I done, but I've learned so much along the way and that's what I'm here for, to share these learnings with you so that you don't have to make the same mistakes that I did. That's enough about me. Let's roll the intro and get into the episode.
Welcome to the time of year I like to call the washing machine. Now I started off being super consistent with these episodes and I know they've dropped off. Maybe you didn't notice. I do find that we're the hardest on ourselves, you know, like I've really backed up, backed off on my social media posts a bit this year and most of you probably haven noticed most of you probably don care so I want you to remember that if you you know being hard on yourself about not doing that thing not doing that social media post not showing up all right because we're the only ones that actually care nobody else cares so why do I call this time of year the washing machine well it's the time of year we have to try and fit in all the things we've got to do the end of quarter buzzers it's the end of the fbt year we've got to fit in tax planning between April to June and we've also got to fit in you know trying to get every everyone every old bugger who's left their tax returns to the last minute to meet the May 15 deadline so from April to June I feel like I'm in a washing machine and then I feel like I get pulled out of the washing machine in July and I can breathe like April to June I'm like being pushed around this washing machine where I don't know about you but even you know we have procedures we have checklists we have a well-trained team we have all the things in place to ensure a smooth April to June but without a doubt every year it still becomes quite stressful because as you know as you're growing you've got additional clients you've got to try and fit into that period and then you want to try and keep all your clients happy even the ones that leave it to the last minute although we did send out some emails the other day basically saying if we don't have your tax return information by the end of April we may not actually be able to do your tax return for you this year so hopefully that'll weed out some of the people that are very very late all of the time and then some of the clients that have prepaid as part of their annual fees we said we need them by the end of april like their information or we may not be able to meet the deadline but it still stressful You know we all like to get stuff done for our clients on time We like to keep them happy And I think we take a lot of that on personally as well Like no matter what we say, no matter what we do, we generally really care about our clients and making sure that they're looked after.
And so I've been having chats with, you know, my other accounting friends lately, and we're all feeling the same. And it seems to be, it's always this time of year and we're like, that's it. I want to merge with another firm or I want to sell my firm or I've had enough. But I think we just need to remember this is a small period of time in the financial year.
And yes, it happens every year. We should be more well-prepared and I try to be, but it's only a small part. And look, if you are listening to this podcast thinking, Natalie, that sounds like my firm all of the time, then that's a whole nother story. But if it's just April to June, it's a small part, we're going to get through it.
And then July, it's going to be, you know, like having a baby, which I don't know about it and have a baby. But people tell me it's like when you have a baby, you forget how traumatic it is. And you go back again and again. So it's a similar thing, right?
It's tax season. It's when we're in the thick of it. It's crappy. We don't like it.
We hate life. You know, it's a time of year. I normally drop off on my gym and I'm not eating the best. And maybe I might have a wine on a weeknight, which is very unusual for me.
But it is a short period of time.
Other episodes covering the same guests and topics, from across The B2B Podcast Index.
S3E15 - Managing a teamS3E14 - AI and Automation for Accountants - Part 2S3E13 - AI and Automation for Accountants - Part 1S2E12 - Dealing with client callsS3E11 - The Perfect Firm
