20 things you should know if you work for yourself
Here are some of my more practical bits of advice - hope it helps!
In the 6 years my boyfriend and I have been together he’s never known me to have a job. As much as he tries, he simply can’t fathom what it would look like if I were gainfully employed. To him, I’ve never had a steady salary, an office to commute to, work to deliver for someone else, or a boss to report to.
I quit my job two months before my thirtieth birthday and met him soon after. Which means, now that I think about it, I’ve only ever worked for someone else during my twenties; a time punctuated by vodka cranberry limes, a million first dates and far fewer second ones, a regretful chapter of going bleach blonde, early-career eagerness and frequent work trips to the Big Apple that left me fantasising about befriending Lena Dunham and living in Greenwich Village full time.
It’s wild to me that I’ve been financially self-sufficient for the entirety of my thirties. I was always entrepreneurial and hungry but working for myself long term wasn’t a given. In the first few years of self-employment I’m fairly sure I flirted with getting a job about a hundred times.
But alas, here I am. Happy, healthy, stable and fulfilled. And in the spirit of feeling grateful for how far I’ve come, I wanted to share some advice that might help you go the distance too.
But first a disclaimer: the information provided here is for educational purposes only and should not be considered financial, tax or legal advice.
The advice
Kicking off with Captain Obvious because I’m a portfolio career evangelist after all: diversify your income. This doesn’t necessarily mean creating 100 income streams (more ≠ better) but having multiple ones means you can spread your risk and, when needed, have more than one money lever to pull.
Mixing personal and business funds is a recipe for money mayhem. Create a separate bank account for your business (sole trader, company, whatever the structure) with sub accounts for general operating expenses, taxes and savings. Get paid into your parent account and allocate money into sub accounts during month end.
Related to the above: run a proper financial month end process. Reconcile your transactions, pay outstanding invoices, calculate your VAT/GST and income tax and move it into a separate account so you don’t get hectic bill shock at tax time, sort out your other allocations and calculate your personal drawings. If this sounds like hell to you, get a bookkeeper!
Keep at least six month’s of personal expenses in a separate slush fund that you don’t touch except when there’s a genuine emergency (like that time I snapped my ACL and realised the $15k operation wasn’t covered by my health insurance) or to top up your personal drawings in low sales months.
This is highly underrated advice but ask past colleagues or clients what your strengths are. Their feedback is great as a testimonial but, more than that, it’ll help you remember how robust your skills and experiences are. Being confident in your value affects everything: how you speak about your work, what you charge, how often you convert, how you feel and the way you move through the world. Collect evidence of your worth like it’s your full time job.
Channel your inner middle aged white man and price higher than you think you’re worth, higher than you feel is comfortable, and higher than you believe is reasonable. This necessary countermeasure is designed to combat your chronic urge to undercharge. If a client responds by saying you’re out of budget, offer to lower your rates by adjusting the scope. Don’t! Undervalue! Yourself!
Adopt the “fee sandwich” approach to stating your price. Reiterate the problem your client is dealing with (first slice), share your rate (the meat), then follow up with the brilliant outcome you’ll deliver (second slice). For example: “What I heard from you is that you’re struggling to acquire new customers because of X. My project fee is $Y and for this I can solve that problem and deliver Z”. Also, eat a real sandwich before delivering the fee sandwich. Hard conversations are harder on an empty stomach.
Offer products and services at different price points so there’s more than one way to engage you. I have a tiered advisory offering (light, medium or high touch) and a tiered portfolio career offering (digital products, six week group program, 1-1 mentoring). My free content fuels both.
In the same breath as #8, don’t over engineer things and provide so many options that it feels like you’re a fast food restaurant. Keep your offer stack simple, sweetie.
If someone has a last minute request and it’s beyond your agreed scope or turnaround time, add a rush fee. I’ve added anywhere from 25-100% depending on the urgency and complexity. If you have to stay up late or bump other commitments, you should be charging for it.
Shoot your shot like you’re LeBron James. Do it in private (via DM or email). Do it in public (via posting online). Do it on Wednesdays. Do it scared. Do it shamelessly. Do it thoughtfully.
A strong email is a personal email. Don’t be generic or vague when you reach out to someone. Contextualise things and reference something they said on a podcast or in the press. Drop the name of a mutual connection to show you’re not a total random. Congratulate them on a recent milestone. Be a human!
I can’t quite believe I’m writing this but…always circle back. If someone mentions their product is going live in 3 months, shoot them a DM asking how it went. If someone makes an introduction and you end up connecting, let the original introducer know. This is how acquaintances become friends, and friends become clients, and clients become cheerleaders.
I saw a tweet recently that said the best networking strategy is helping people and I COULD NOT AGREE MORE. Go above and beyond, make intros, gas people up, congratulate them, be generous, refer work on, help out where you can. Put good karma into the world and it’ll come right back atcha.
Build an email list. My whole content strategy is Substack-first because I never want to wake up and see that my entire online presence has been deleted by Meta’s overlords (this happens more often than you think). Own your email list, own your distribution, sleep easy at night.
Instead of spending precious time allowing people to pick your brain for free, share your knowledge en masse by creating content online. Take every single question anyone’s ever asked you and turn it into a post. This does two things: it gives people free access to your wealth of knowledge while building your reputation and credibility.
Have a point of view and share it online, whether it’s about your industry or field, business, careers, creativity, media, AI, 17th century Shakespearean plays, alien disclosure, why coloured tights are having a moment, the upcoming American royal wedding or why everyone has a Substack now. Being authentic is way more important than looking perfect.
Softly seed your offers, over and over, forever and ever, for as long as you shall live. Mention them here and there. Sprinkle them across your content. Pepper them in conversations. Repeat them so often that speaking about it feels natural. Much of the time this will feel pointless but think about it like you’re planting seeds that, over time, will take root.
Take! Time! Off! You! Need! To! Refuel!
A lot of people will give you advice and a lot of it will be terrible. Always proceed with caution.
Do you want to start building your portfolio career and taking full ownership of your earning potential?
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Diving into #8 (tiering your offers) and #14 (the best networking strategy is helping people).
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Saved this in my folder:
Channel your inner middle aged white man and price higher than you think you’re worth, higher than you feel is comfortable, and higher than you believe is reasonable. This necessary countermeasure is designed to combat your chronic urge to undercharge. If a client responds by saying you’re out of budget, offer to lower your rates by adjusting the scope. Don’t! Undervalue! Yourself!
You are pouring gold again 👍🏼
As always, loved this post
"Channel your inner middle aged white man" - amazing, hah!