Most Challenging Obstacle in Personal Finance.

[SustainableHappiness]

Most challenging obstacle – I waffle between two.
1) Patience while milking my current job for more $$
2) Living my own lifestyle goals, not EREs, not MMMs, not yours

Hardest goal to achieve – Not quitting today, not quitting tomorrow, not quitting until October when Phase 2 of the plan begins

Anything hard if following a system – No, but I am a straight index fund investor in the accumulation phase using a prefab Canadian Couch potato fund mix. It’s a waiting game, which a la the first challenging obstacle makes it hard.

[Seppia]

Most challenging obstacle: for me, it will for sure be the ability to actually leave my job when I'll be ready.
I don't like some aspects of my job (too demanding both mentally and physically), but it pays very well by Italian standards.
I am ultra conservative with my money, so I know I will suffer from very extreme "one more year" syndrome.
My "phase 2" will involve what is usually referred to as "work", namely being a teacher (I always adored teaching to kids), which in Italy is a badly paid (but still paid) job, so I hope this income will help me overcome my hesitation.

Hardest obstacle and anything hard if following a system: so far I've encountered no meaningful obstacles, I naturally look at the long term and I'm very disciplined.
When you couple these two attributes with a high salary the path to ERE is very smooth.

[leeholsen]

I think the most challenging thing is spending.

your ability to control your spending, which the exception of a big expense you cannot control like a medical condition; is the greatest hinderance to retiring/climbing the wealth ladder/etc. imo, most anyone can retire earlier than expected even on an average income is they can control spending and limit it to needs, following much of what is put forth in the ERE book.

[7Wannabe5]

Making myself work full-time for long enough stretch. I can readily find employment at more than 4x my frugal lifestyle spending, but I have the opposite of the problem of not being able to quit and/or fretting that I won't be able to find things to do with my free time. Soon as I get one solid delectable morsel of free time saved up, I tend towards irresistible urge to gobble it down immediately.

[classical_Liberal]

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[CountHigh]

Nice to note that others are struggling with similar things as I am. My TOP3 are: 1. Finding time/energy after work and family life to learn skills that would save money on a long run. This is a big one, because it also defines what I do, what I know, and (partly) who I am. On a smaller scale, quitting solving problems with money (e.g. repairs, eating out). 2. Life-style discussions with the family that often involve money. My SO is supportive, so this could be much worse. 3. Having quite expensive retire-to -dream that requires capital (building a house). It would cost me about 4-5 working years extra to follow that dream. I try to find ways to downscale the dream or related expenses.

Number 4 would be lack of self-discipline at times...