I struggle with scaling up my business. I have been working from home for the past 10 years and I have websites that generate ok money ($100K/y). My struggle is I just can't get myself to hire my first full time employee. I tried it many years ago but after facing the headache of hiring, dealing with attrition, training, etc, it took away all my focus from work.

I feel management is a skill I just don't have. Also working from home, staying with my family i now lack the motivation to get up on time and commute, go to an office, etc.

Yet my business is as is for the last many years. I've tried hiring freelancers and VAs but that too never lasts for more that 2 months. Hiring freelance programmers has also never worked for me and in the end I always think it would have been easier if I had done it in the first place.

So that is my biggest struggle for many years now :(