It’s summer (in the Northern Hemisphere).

Your out-of-office is tempting you. But if you’re a solo finance lead in a startup, juggling reporting, payroll, board prep, and a few surprise “quick questions” from the CEO. This idea of stepping away can feel... unrealistic.

The truth? You can take a break. Even if you’re a team of one. But you need to get intentional about what you delegate and how.

Here’s what to hand off, what to prep in advance, and how to avoid coming back to an inbox that's on fire and 57 Slack messages starting with “just checking...”

Step 1: Know what must keep moving

Start by working out which finance tasks can’t pause while you’re away. In most startups, this includes:

• Payroll and contractor payments
• Supplier payment runs
• Month-end cut-off (if your holiday crosses into a new month)
• Investor reporting or board packs
• Any tax or compliance deadlines (e.g. VAT or R&D filings)

This is your non-negotiable list. These are the tasks that someone needs to own in your absence.

If you’ve got a bookkeeper, ops manager or part-time FD, great. But even if you don’t, now’s the time to get a bit creative with resourcing and pre-planning or scheduling.

Step 2: Make the most of your bookkeeper

Even if they’re outsourced, your bookkeeper is your resource. Before you head off:

• Confirm payment run dates and give clear instructions.
• Ask them to flag anything unusual in the week before you leave (e.g. missing invoices, Xero not matching).
• Set expectations around how they’ll handle queries while you’re gone.

If they’re not usually customer- or investor-facing, prep canned responses they can use if someone emails.

If you’ve got a board meeting coming up, get your bookkeeper to start the month-end process a few days early. That way, you can review numbers before you go and avoid a scramble when you’re back.

Step 3: Don’t DIY everything. Prep docs others can run with

Delegating doesn’t always mean giving someone a job. Sometimes it’s about equipping them to help themselves.

If you don’t have anyone to “handover” to, write these up before you go:

• A 1-pager with what’s due and when (e.g. payroll by 25th, invoice approval on Thursdays).
• A list of emergency contacts (e.g. your accountant, R&D advisor, HMRC login info).
• A “where to find it” list, especially for recurring tasks like payment runs or payroll journals.

You don’t need to over-engineer this. Just make it easy for someone else (or even you, post-holiday) to pick up key workflows quickly.

Step 4: Set expectations with your CEO (and the wider team)

Your CEO is probably still going to WhatsApp you on Day 2 of your break. So have the conversation before you go.

Explain:

• What you’ve delegated and what will still run.
• What you won’t be checking or doing until you’re back.
• What to do if something urgent comes up (and what counts as urgent).

This builds trust and shows you’ve planned ahead and not just dropped tools and ghosted the business.

Step 5: Use tech to do the heavy lifting

You don’t need to go full automation, but here are a few tools that can reduce noise while you’re away:

• Email autoresponders with links to your FAQ doc or escalation contact.
• Slack status or pausing notifications so people know not to expect a reply.
• Scheduled invoices and payment approvals in Xero or your finance stack.
• Asana/Notion checklists so others can tick things off while you’re gone.

Bonus points if you set up a recurring checklist you can reuse every time you take leave.

Taking a break holiday is possible. Even solo.

If you’re overwhelmed in a finance team of one, the idea of a proper holiday can feel out of reach.

But building systems, even simple ones, helps you stay sane, protect your boundaries, and stop your holiday becoming “just another week working from a beach.”

Taking time off is part of being a leader, not just a doer. And if you want to build a sustainable finance career in startups then you’ve got to start somewhere.

Start with a one-week break.

And if you want help putting the right systems in place (so you can take that break without guilt), that’s exactly what we cover in the FLF course. You’ll learn how to build scalable finance workflows, manage stakeholder expectations, and move from being the person doing everything to the one running the function.

Want to become a confident, strategic finance leader in a startup within the next 12 months? 

Here’s your plan:

1. Subscribe to my YouTube channel for weekly practical tips and real talk about startup finance leadership.
2. Read my book Financial Leadership Fundamentals to get clear on what’s expected of you and how to show up as a leader.
3. Join the Financial Leadership Fundamentals course to fast-track your growth with structure, support, and strategy that works in the real world.