table of funtents

1. 👋🏼 it’s me, hi

2. 🌴 founder’s guide to time off

3. 🎁 a different kind of gift pt. 2

4. 👑 misfit wisdom nuggets

👋🏼 it’s me, hi

HI FROM 30,000 FEET IN THE AIR!

RE: last week, looks like we have indeed learned the election results together 🫠

The biggest lul is I’m actually flying to the states AS YOU READ THIS RIGHT NOW (for those who didn’t know - I’m originally from sunny California).

No idea what I’m walking into though. Will report back on vibes next episode.

I’m going to stay on brand today and talk about something NONE of us has a playbook for: taking time off when you’re running a business. 

Hard to do, laced with guilt and a financial mind boggle; but also necessary.

SO PUT THAT OUT OF OFFICE ON, make yourself a sunny bevvy and hop on board the SS keshty (en route to your next holiday, obvs) 🚢

🌴 founder’s guide to time off

I caught up with someone this week who kindly said, “you seem to really have this whole boundaries thing nailed with keshty.”

This is a No BS newsletter, so hear it directly:

1. Kudos to me for deceiving all of you 🤡

2. Taking time off is a work in progress that FULLY requires discipline and intent. You heard me right - just like your gym and journal habit.

Y’all are adults, so I’m not going to patronise you. I’m simply going to offer something you already know, but maybe need to be reminded of.

You need to (occasionally) take time off.

“But Neds! I simply cannot rest unless things are actively moving, I can’t just turn my brain off and HONESTLY HOW DARE YOU even suggest otherwise???”

In my full-time era, I actually found it easy to switch off once I was away - but I could not FOR THE LIFE OF ME shake off the dread of what I’d be coming back to. I’d spend a whole lotta holiday thinking about it.

And I know I brought all these habits with me into self-employment.

I also know the many “self-made” founder brole models out there preaching 5 AM starts, 38 hour workdays and missing your own wedding in service of the “grind.” (FYI: if this isn’t in line with your idea of success, respectfully - bin it).

1. why you need a holiday

Why founders should actively take time off:

🧠 foster creativity

The only way out isn’t always through. Sometimes, when we’re too close to a particular challenge, a physical change of scene or separation offers a new approach. Taking time away (AND pro-tip: away from doom scrolling*) enables us to creatively come back to existing issues AND generate new ideas we otherwise didn’t have capacity for.

🧘‍♀️ gain perspective

A humble reminder that we are NOT the centre of the world and no one will die if we’re uncontactable for a few days (or weeks!). We’re always going to be the most involved in our business, but we need to remember no one cares as much as we do, and actually, others will appreciate getting the best of us.

💪🏼 set an example

If you lead people, taking time off is mission-critical. It normalises your people should listen to their internal battery reserves and prioritise their health too. If you model overworking, your people will follow suit to stay in your good books. Nothing quite like a perpetually exhausted team trying to run a marathon, eh?

2. how to actually take one

💰 budget in advance

Money coming in is WELL NICE, so it’s extra important I remind you to physically budget for time off. You no longer work for an employer - you work for you, and only you can grant you paid leave.

When considering your pricing, factor in a % uplift based on how many days you’d like to take off vs. how many you plan to work. Fail to do so, and you’ll find yourself in a feast and famine cycle where you’re either spending all your money funding holidays, or finding it impossible to justify the holiday at all.

💌 pick clients who care about human you

A lot can be said about your clients when holidays roll around. When I had my wedding back in May, I was so scared to tell two existing clients I’d be off + a new client I’d just signed on that I couldn’t start for a month.

I gave plenty of notice, made sure nothing was left undone and learned very quickly: everyone was actually happy for me. They were fine, respected my time while I was off and I didn’t lose any business. If someone does make a fuss, remember - the beauty of doing your own thing is you can choose not to work with assholes.

🔥 don’t come back to a forest fire

Wait, how can I control this? A fair question, given we’ve all been through that OTT employer who’d schedule a 9 AM the day you got back to complain about everything that went wrong while you were out.

But you run your own business now. Your clients know you’re off, you have an Out of Office on and you’ve blocked your calendar for the first few days you get back. That’s really it. As long as YOU don’t see your business as capable of a forest fire, then NO ONE else can make you come back to a forest fire.

3. no bs where I got it wrong

💩 squeezing every last bit of work pre-hols

Recently, I combined 3x client work for October / November into 5 weeks so I can be off from this week. Pro: I’m not missing out on cash flow for both November and December. Con: I pushed beyond my limit and CRAWLED to the finish line. I spent most of October dropping the ball on my own metrics for a happy life, saying no to exercise and healthy meals to do more work. Not my best vibe.

💩 automating content

This sounds counter-intuitive; surely we should automate content to go out while we’re away so we come back to growth? I tried this with LinkedIn and found myself needing to engage with comments in real time. If your goal is meaningful relationships and not transactional growth, you can’t in good faith pretend to be open to engaging when you’re not. I made a decision not to schedule content anymore for times I couldn’t interact live and it’s changed my holiday game since.

💩 doom scrolling

I suffer from a weird form of FOMO where I end up scrolling LinkedIn / Instagram to make up for the lost time I spent DOING MY JOB. It’s been the death of my opportunities for a good break. On the flip side, I’ve found boredom to be the greatest gift while I’m off + actually look forward to an 11 hour flight (e.g. the one I’m on now!). Nothing stirs creativity, enthusiasm and reflection like periods of time without mental stimuli, so don’t forget to build “doing nothing” into your holiday plans.

🎁 a different kind of gift pt. 2

🔊 We interrupt our regular #SmoothOperator programming with an update:

In episode 5, I put a poll out asking how to thank you for referring the minority misfit to friends. Today, I’m announcing the first gift drop (yes - consider even more options in future as we grow!) based on your feedback and suggestions.

From now on, you’ll receive the following thank you gifts for referrals:

• 1 referral: the Scale MOT template we use when auditing potential clients (by popular demand after episode 6!)

• 5 referrals: keshty’s digital stack, which includes (1) our prospect intro slide deck and (2) our client proposal template.

• 15 referrals: exclusive keshty merch, from bags and pens to stickers and mugs!

Remember to refer using your special link at the bottom of each newsletter so I can gift accordingly, and mega thanks again for wanting to share my rambles with others 🫶🏼

👑 misfit wisdom nuggets

✍🏼 Nicole Gray, Founder at Five to Nine and one of the epic brain-humans behind this very newsletter, writes:

“If I could do it all again, I’d ask for help sooner. 

I’d be more honest and vulnerable about what I wasn’t confident in / what I didn’t know. For the first five years of working for myself, I didn’t have a network of people doing similar work (most of my friends went down the corporate career route!), and so my main points of contact at work were my clients, or freelancers I’d hired.

That meant that I put a huge amount of pressure on myself to get everything right and ‘be perfect’. Spoiler alert: that never works.

Leaning more on my community of female founder friends over the last few years and actually being vulnerable about what I’m struggling with has not only helped me build stronger ‘business friendships’, but also helped me become a better founder — I’m faster at solving problems because I’m not trying to do it solo anymore.”

** PS: I LOVE Nicole’s newsletter with a capital L. If you’re curious about all things LinkedIn sprinkled with a fantastic sense of humour, look no further.

📣 HEY MISFIT! If you’d like to be featured in an upcoming issue, email me with your answer to this question and LinkedIn profile. Let’s learn together 🫶🏼

Thanks for joining episode 8, misfits! Give me one week back here and it’s likely I’ll start calling all of you “dude.” To be confirmed.

Before you go, let me know what you thought of this issue with the pulse check below! Good intent feedback is always welcome ⬇️

xo, Neds