Dress for success

I see lots of ill-fitting khakis and polo shirts. It's not a great look. Very blah.

If you're going to become a successful 1099, you don't need to dress like a fashion model.

However, you should get clothes that meet two criteria:

• Fits well (fits your body size and is comfortable)
• Mildly fashionable

Over a two year period I'll lose about 10 pounds and then gain it back. When I'm down 10 pounds, my clothes fit great! When I'm up, not so great. Those pants feel tight around the butt and thighs. It's uncomfortable to sit and not a great look.

My normal instinct is just to not buy new clothes and lose the weight so I fit again. But at best, I'm inconsistent at that and then in the meantime I have to wear the uncomfortable clothes, which makes me more uncomfortable at work, which makes me resent going to work.

This is not good if you want to give out positive energy with your clients.

So buy clothes that fit and are comfortable.

The next criteria is to be mildly fashionable.

I don't know anything about fashion, nor do I care.

But, buying a button up work shirt with an interesting pattern or color will give you a little boost in confidence.

If you dress like a slob, you will feel like a slob, and that energy comes out when you're working with clients.

One hack is just to buy clothes from slightly more expensive brands whose designs are current. I won't speak for women, but for men, Bonobos usually has a more modern look. I now just order from them a few times per year.

Spend a little money to look and feel good. It's a worthwhile "business expense."

Want the full playbook? Check out Going 1099.