Politely recommend budget help to a friend who owes me money?

Question

To address duplication concerns, this belongs on IPS rather than workplace stack exchange or finance, as I would like to address the specific issue of recommending budget help, and handle this as a friend rather than as a colleague, so am looking for an IPS specific answer (although I won't mind if you feel there is something important business wise / finance wise I should know that can help going forward).

Context: I run a consulting company, and am in a very stable financial position. Bob is older, has a very well paying job and family. I've had a ~6 year friendly relationship and ~3 year professional relationship with Bob. Both in Australia.

Over a period of time I have worked with Bob on a few projects, he's always been a nice guy, and in previous projects he's always been above board and whenever he'd invoice I'd always promptly receive the agreed split.

The last project I did with Bob we invoiced in two installments. Initially it was agreed that installment A and B would be split 50/50. However, at a later date, Bob requested if he could receive A in full for use in an upcoming (long overdue) family trip.

I agreed to this, however, a few months down the line, I had not received payment for installment B either. In terms of monetary amounts, this is not critical and will have no effect on my business (was only ~$1000-3000).

I invoiced Bob for this, then after 30 days received a call from Bob asking for leeway on the invoice due to unforeseen financial circumstances (that were explained, refinancing issues and medical bills). I was happy to offer this indefinite extension, and even if he were to say "I can't pay this" I would simply tack the price onto the next job we do together, and invoicing would go through my company.

I know that Bob is not in the best position financially, it seems that the main problem is not his income (he'd be earning 200K+), so I am sure that if he had budget help his position could improve considerably.

I'm going to be meeting with Bob soon for a catch up. I would like to recommend that Bob seeks budget help, but there are a few additional factors in the equation (hence why I'm asking here):

1. I'm much younger, in my 20's and he's in his late 40's, so I can't use my normal approach of directly relating to experiences in my own life
2. I would like to maintain a friendship with this person. I believe we have a good relationship, and would feel comfortable discussing other personal topics, but this is one that could potentially be very difficult to navigate.
3. I am willing to give the option to waive the debt on the condition he seeks professional budget help (all the business minded people here will be screaming no), but I don't know if this will help the discussion. I have no problem with alternate payment arrangements in terms of time.
4. It is possible his wife is the main person in need of budget help, so any approach I take would also have to address the alternative where it is his wife who needs to seek help (which would be another question in itself), so for this question, how do I continue if this is the case?

I'm also happy for answers that say do not do this, but answers that allow me to achieve an outcome that improves the overall quality of both our lives are favorable.

Update 1

There may have been some confusion with my initial post so to clarify a few things:

1. I expect the money will be payed, he has stated he will, it will just be a matter of time. Option 3 above is only relevant if that could help with the discussion of seeking budget help.
2. I don't necessarily have to or want to involve the amount outstanding in the conversation, but this was the context of what prompted me to ask this question.
3. I would like to bring up him seeking budget help as a friend, because I feel like this could improve the quality of his life, as I have observed over a long period that money is a limiting factor in him pursuing some things

Answer 1

I think that making this recommendation would very likely end both your friendship and your professional relationship with Bob.

There are things that adults just can't get away with, with regard to other adults, and I think that this is one of them. In particular, the offer to forgive the debt if he gets budget help feels very much like a parent rewarding a child. Just as you wouldn't offer to cut his meat, comb his hair, tie his shoes, or buy him an ice cream cone as a reward for brushing his teeth every day, I don't think that you can make this offer.

Also, if Bob earns 200K+, I doubt that his problem is as simple as budgeting incompetence. His money woes are probably related to some pretty entrenched habits--maybe a shopping addiction, maybe a gambling addiction, maybe an issue with drugs--and your entering this private area of his life is likely to threaten whatever veil of secrecy he has around those habits. If the issue is his wife, that further increases the odds of the destruction of your relationship with him.

He owes you money. The best way to deal with this is, IMO, to require him to pay you. I think that it's unwise to tack this amount on the next invoice, because I don't think you can count on him paying that next invoice.

Answer 2

It seems that the issue is not that Bob needs budget help, but the fact that he owes you money! There's nothing wrong with claiming money that you are owed, in fact, it's an important to insist upon this. This wasn't an emergency rent payment that you gave to a family member in a crisis; this was money that Bob owes you in a professional context and it is his responsibility to pay you back.

In fact, it is probably inappropriate for you to insist that Bob get budget help, given the nature of your relationship to him. How would you hold him accountable for budget help, since you would accept that instead of your payment? If Bob were financially dependent on you and was spending your money frivolously, that would be a different situation, but it looks like this is a simple failure to pay a business expense.

To be sure, nothing incentivizes/motivates someone to budget their own finances like having to pay money that they owe.

There's no reason you can't carry on a friendship with Bob. Perhaps he needs to pay you back in installments, or perhaps you can set a deadline. Listen to him with compassion, but don't feel that you are overstepping yourself to inquire calmly about a business expense that he owes you.

It sounds like Bob has a history of paying on time and has a friendly relationship with you, so if he is going through a rough time financially, he will probably let you know, and then you can figure out where to go from there.