Let’s talk about money. Regardless whether you’re thinking about leaving your job, re-training for a new industry, going part-time or rolling the dice to become a founder, this is one will be the top concern. Money to support yourself, family perhaps, and for some, maintain your current lifestyle.

So what is risk?

Founder Amy Thomson shares her experience and wisdom on evaluating real risk in our conversation. When Amy founded her app Moody Month, she took the biggest leap of faith to make it happen: moved to America to get the funds to fuel the technology and sold her house to get the cash flow. A straight up personal risk into business. A move, she describes, that she would never advise anyone to do, citing it as the biggest and most stressful decisions of her life. But it paid off. The product was built and it worked.

"Evaluating your own personal financial circumstances in the process of building a company is really important because your situation will impact on the success...

It's not just what you're willing to do. It's also how you evaluate those decisions to ensure that you're comfortable with any outcome, negative or positive... being comfortable with the fact that that decision might not be the right one, right?

So in looking at how you take those steps (for career change), you have to always come back to what do I believe my skill sets are? What can I achieve within those skill sets? And do I have the capability within that skill set to potentially change the course of this if the environmental factors are different?"

So, where to start when trying to get clear on the level of risk if you are thinking about leaving your full-time role?

Let's begin with actual hard numbers and personal finances. What do you currently do?

Do you clear out the kitchen table, roll out a budget planner, bank statements in a pile to suss out all your incomings and outgoings? Make a lovely spreadsheet?

For many, it’s not straightforward. 1 in 2 adults in the UK (that’s 24 million people) do not feel comfortable with their day-to-day personal finances.

Financial literacy is also a huge problem, one where more and more schools are trying to introduce lessons on financial resilience for everyday living. Reports also show an education gap related to pensions and retirement planning. In short - there’s a ton of evidence highlighting the fear and the lack of inclination to deal with annual finance planning. I know folks who are whip-smart, super-responsible and great with their project and work budgets. But when it comes to dealing with their personal finances? Game over. And let’s not even talk about the number of folks, globally, well into the millions, who don’t fill in their tax return on time. In the UK alone, tax deadline day in 2025 saw 31,442 people submitting their return in the latest possible hour, between 11pm and midnight. That shows how scary and baffling it is for many.

(Side note: I knew someone who did their tax return after their missed deadline and got fined. So they decided to fill in the return, whilst having a bottle of wine, but got all their figures horrendously wrong, and got fined exponentially more than their original missed deadline fee. Learn from others, team. It should have been one of those mini bottles).

Regardless of our own financial confidence, we know the immense worry about leaving our regularly paid jobs. It’s the top concern when exploring your own life/career changes. For my situation, the thought of leaving my corporate paying job led to immediate apprehension and fear; how was I going to support my family? What would my parents think? With my own upbringing and then working in a relatively poorly paid radio industry, getting a job at a massive global company back in 2015 completely changed my life. It also fundamentally changed my sense of financial security for a decade. Of course it did. Those privileges I then started earning (in all aspects of my life) were clear.

So I’ll be honest, when considering the switch, despite my track record, success and being very clear on my values and purpose, trusting myself in what I was going to build - it was the biggest, mental sticking point. But what I can say, looking back, is I kept this personal fear in my head for a while, despite huge support from my family. And the only thing I could do, or be in control of, was use all that agitated energy to drive me to do something about it - to understand what I needed to budget to survive. The trick was to do this planning earlier rather than later i.e. get a reality check on what I needed not just to survive, but to sustain a good lifestyle, and what I was willing to sacrifice for the next couple of years to get there. That’s what gave me the confidence to move on.

So with any life/career decisions, get your house in order first. You’ve got to get a grip on your incomings and outgoings over a typical year. You’ve got to have a base understanding of what you need to take home every month to pay all the bills AND have a social life so you can actually start understanding what options are in front of you.

So these are the next steps in tackling the same fear you’ll have, whatever options you’re exploring in your life/career changes.

I originally worked out my annual incomings and outgoings with a pen on a massive A3 sheet of paper (taken from the photo copier at work, natch). Everything from holiday spend to how much my kid had accumulated at the bubble tea shop (way too much). All in hand drawn boxes, analogue style. That worked as a first step and I felt so much better for it. But I did have all the paperwork in hand and I do regularly check on personal finances, which I’ve done from a young age, a result of supporting my mum and dad with their restaurant paper work, as English wasn’t their first language.

Here's where the financial experts come in who have created easy-to-use templates far superior to what I used: A3 sheets of plain paper stuck on one of those massive dinosaur posters they give away free in newspapers. Old school pen to paper.

First option: the rock-solid folks at MoneySavingExpert have very decent budget templates and real-time best deals on household savings, allowing you to get to grips with your outgoings. And this is the thing, they outline their planners annually (far more useful) as well as monthly. I have to give total props for making their excel sheets not actually look like excel sheets (a papercut to the eyeballs for many). In fact, it’s super simple to fill in. The planner also accounts for all the random stuff including special treats (shout out to all my local take-outs, especially the lovely Mohammad for his continued Friday night support) and the inevitable ‘I forgot how much my kid’s football birthday party cost plus getting that KFC party bucket delivered’ being accounted for in your budget - it’s based on real life incomings and outgoings.

Here's that user-friendly spreadsheet for you:

https://www.moneysavingexpert.com/banking/budget-planning/#spreadsheet

One other source of excellent ‘get your sh*t together’ support is the Money Clinic led by FT’s brilliant Claer Barrett an award-winning finance journalist who specialises in personal finance. I’ve been following Claer’s super welcoming, straight-talking and easy-to-follow advice through FT weekend, and enjoying how she talks about money matters (including things you didn’t think you needed to know about!) in everyday language.

Claire has a super handy course aptly named ‘Sort Your Financial Life Out with Claer Barrett’ 6 modules over 6 weeks (£19). Similarly to Oh Yeah, it’s self-paced and offered via a digestible email sent to your inbox every Wednesday. It provides short pieces of advice, almost like a checklist, including how to negotiate a pay rise (week 5) and how to be as tax efficient as possible (week 2) and a mortgage masterclass (week 4).

What I really like is Claer's approach in understanding that we do have an emotional relationship with money. And how we have to understand that first before doing any practical tasks, pausing and reflecting before making any big financial decisions. In short, noticing the emotional and physical triggers that could drive financial decision-making is the first step to a healthier, steadier relationship with money - and of course, facing the fear of it overall.

For example, digging deep on your spending habits and reflecting on what value you get from each purchase. It's knowing how to save better and making informed decisions. As Claer says,“…please don't feel embarrassed about how little you may know about money...we are not taught about any of this stuff in school. Even if you earn a lot of money or come from a wealthy background, this does not automatically make you brilliant at managing your cash.”

Exploring freelancing as your next move will be a prime option for many, but again, moving away from a stable salary and being unsure of the finances = fear. Which is why Oh Yeah has welcomed the expertise of Priya Joi, who has supported so many in the freelance community, particularly writers. As a science journalist for the last twenty years, Priya has experienced it all - client demands, several breaking points and a lack of boundaries. Not only is Priya brilliant in sharing her methods in how to make more money through business savvy decisions, but also how to keep both integrity and personal care top of mind. Time management skills are imperative. Explore more of her wisdom and actionable tips in our epic chat where she busts many of the fears around freelancing life.

In order to feel more confident about your next step, you do need to face your finances. I’m afraid there’s no magic bullet other than ‘just do it’. But I promise, you will feel awesome once you do complete this. Like some sort of Arthur drawing a sword out of a stone. I’m sure there’s a better analogy, but just roll with it. I promise you’ll feel proper proud for investing the time to do this early-doors.

In the next chapter, we take a look at emotional support through change.

The Oh Yeah Juice