Shore Thing

Nobody sits new business owners down and says: hey, you might owe the IRS four times a year now, not once. So let’s have that conversation before the penalty notice does. When you work for someone else, taxes get taken out of every paycheck automatically. You barely think about it. When you work for yourself, nobody’s withholding anything — which means the responsibility for sending that money to the IRS throughout the year now belongs to you. That’s what quarterly estimated

Mention the home office deduction to a small business owner and watch them get nervous, like they’ve said a phrase that triggers an automatic IRS response. I understand where this comes from — it has a reputation as an audit magnet, mostly built on outdated advice. Let’s actually look at it. What it is. If you use part of your home regularly and exclusively for business, you may be able to deduct a portion of your home expenses — a slice of your rent or mortgage interest, uti

When you worked for someone else, retirement savings may have been almost automatic — a percentage pulled from your paycheck, maybe an employer match, a decision you made once during onboarding and mostly forgot about. When you work for yourself, nobody sets that up for you. Nobody matches your contribution. If it’s going to happen, you’re the one who has to build it. I bring this up because it’s easy to postpone indefinitely — not because it’s not important, but because ther