How to file/Should I file?

Hi there,

 

I just accepted a job offer paying $90,000/year and I think I am in a different tax bracket now (compared to before when I was making $54,000). Since they are taking a larger percentage of money from me via taxes, does that mean my return in April will be larger than ever before? Also, I've historically chosen the option to withhold more taxes NOW for a larger return LATER. but I'm wondering if that's actually the best move, or if I should be choosing to receive more money NOW?

Secondly, I am about to become certified as a personal trainer/nutritionist and will help coach people on the side for payment. If I earn a hypothetical (extra) $20-30k a year from that. Would I have to report that, even if it was Venmo'd to me or paid in cash? And if so, how would i report that for taxes? I don't want to get hit with a lofty sum that I owe.

 

Thank you very much,

Andre