One of the lamest things about deciding to step away from unfulfilling (yet steady-salary) work is having to deal with ‘the money question’. The topic is covered in The Escape Manifesto but ultimately it’s a question that only you can answer.

We each have different thresholds when it comes to risk; our own tastes when it comes to lifestyle; our own preference when it comes to financial security. Only we can decide exactly what we’re willing to sacrifice in exchange for whatever else. That might be the toughest thing about Escaping – figuring out where we sit on our own spectrum and moving away from the person we thought we would once become.

One of the toughest emotional battles I’ve had to face (and am still facing) is the extent to which to accept financial support from loved ones. I know I’m not alone in this – I meet members going through this battle with their ego all the time.

Maybe it’s a spouse offering to temporarily become the key breadwinner – you work on your startup and be penniless, while he or she takes the full-time job. Maybe it’s a friend you’re starting a business with who bankrolls the two of you. Maybe your parents don’t necessarily offer to help you out, but you know you can ask them for money if you ever get really, really strapped for cash.

It’s not about the money.

It’s about what the money represents. Especially if your parents are the ones lending you the cash. It’s about power and politics and wanting to achieve independence and realising that you kind of have but kind of haven’t.

When you get to a certain age, you want to feel like you’re in control of your own life. You want to at least behave and look and pretend like you’re a grown-up, even if you don’t feel like one inside.

It doesn’t feel great to have that money conversation with your parents. In fact, it can feel awkward at best, or humiliating if you catch them at a bad time. Personally, it makes me feel like I’m 13 again, holding out my hand and asking my Mum for a note in her wallet so that I can go to the movies with my friends. It just makes me feel like I did a really crap job at ‘growing up’ – I should have it all sorted out by now! I shouldn’t need their help!

But sometimes, especially when it comes to investing in yourself – if your parents are lucky enough to be in a position to help you out financially – you need to ask them for help or else you’re going to miss valuable opportunities.

Every choice comes with an opportunity cost.

There’s an opportunity cost in not borrowing the money and not doing the course. Or at least that’s what I tell myself, to alleviate my own guilt.

I also tell myself that there’s a difference between expenditure and investment and that I’m smart enough to spot the difference. It’s one thing to ask for cash so that you can engage in frivolous expenditure and quite another thing to approach your parents about becoming silent business partners in the construction of your career.

It’s important to know what ROI you’re buying, in terms of education products, and to beware of educational Ponzi schemes. Formal education is often touted as an ‘investment’ but to be honest, some of the fanciest-looking and most ‘prestigious’ badges are still crap investments if they’re not leading you to the place in your career that you ultimately want to get to.

We each battle with these issues.

Currently, my own internal money question is around graduate school. I don’t know if I can realistically afford it. I don’t know if I want to take out a student loan. I tried broaching the subject with the Bank of Dad the other week and just had a very awkward conversation that somehow escalated into a political argument and had me re-thinking my entire professional life in general.

When I meet members considering doing the Startup MBA who are struggling with how they might approach their parents to lend them the cash to do it, I give them the same advice that I tell myself: only you know where you want to take your career. Any education you invest in is a tool towards getting you there. You are smart enough to spot the charlatans selling faulty tools.

If you think you’ll look back in five years and regret the decision, don’t do it. But if all that’s stopping you from making a logical investment into yourself is the emotional discomfort of one or two awkward conversations, then perhaps meditate upon the alternative – not doing the course, not making the change, not learning new skills – ask yourself if that’s a price you’re willing to pay.

Our Startup MBA covers everything they don’t teach you in a traditional business school. It’s a steal at £750. We’re offering an early bird-discount of £680 if you sign up before Tuesday June 11 and if you sign up with a friend, we have a ‘Bring a Buddy’ discount of both of you only paying £500 each. You can read more info and apply here and email me directly if there are any further questions about modules, payment plans, and speakers:

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