Real life advice before considering freelance over F/T

Working freelance is a fantastic way to keep yourself in an environment you love and control your own destiny. It’s a completely different and very rewarding lifestyle from that of a F/T office job. There are a few things to consider seriously before making the jump.

  1. You will need to pay your own insurance 100%. Be prepared to layout at least $350/mo.
  2. You won’t be receiving a refund check from the IRS and State at the end of the year. You will OWE them.
  3. You will need to set aside at least 1/3 of each paycheck to put aside for paying taxes AND NOT DIP INTO THIS MONEY. If your taxes are too big for your budget, you can arrange for payment plans, however this will be another monthly expense.
  4. You’ll likely need to have more than one client at a time, or at least have one guaranteed project in the wings.
  5. You must be committed to a daily routine to keep you on track. It’s easy to say “not today”, but don’t do it very often! Time is money.
  6. You will have to be your own advocate. That means having to chase down invoice payment.
  7. You have the option to work through a freelance agency, which can be very helpful.

Anyone else have some real-life advice for people who have never done freelance before?


Network, network, network.

I freelance without insurance. Can you tell me a little about the insurance you have and what it’s for? Has it been required for your work?

I had 2 freelance jobs through agencies. The con being they take a percentage of your hourly rate. The plus being they can get you into companies you might otherwise not have access to. They also handle all payroll & taxes are taken out. You receive a W2 at end of year from the agency.
The best freelance (permalance) set up I had was with a big company that used an outside payroll service to deal with contractors. Again, taxes taken out, sick days provided, and after a set time I had 401k and health insurance too. I don’t think the service took a cut of my pay either. Basically the only perks I didn’t get were paid vacation days.

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Hey! Im just curious which agencies you went through to find your freelance work. Im looking to start freelancing for the first time and am trying to see what experienced freelancers recommend.

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I am paying $320 for health insurance monthly. It is certainly a big expense.

This is my first year doing FT freelance, so I am dreading the tax process I am about to embark on! I worked hard to save all that 1/3 in my savings account. So I should be okay, but it will suck to watch that money disappear!

Your point on staying committed to a routine is super important. I was doing WFH for a full time client for about 4 months. Then they didn’t need me anymore. Two of my smaller clients dropped off after the New Year. Ive been in a bit of a funk, trying to figure out my next move. I let my schedule slide and really got disorganized and was wasting my day on minor things and getting distracted so easily. I wasn’t working towards any goals. I HAVE to write down to-do lists and cross things off. Otherwise I never get anything done. There is a lot of self discipline involved in freelancing.

You also have to deal with bad clients. They can seriously impact your mental health if they are sucking up all your time and being too demanding. You have to stand up to clients and it can be hard to muster up for the conversation when you know it won’t go well. Its been a challenge for me.

My problem with agencies is that they always have positions for Freelance/Temp to Hire. Like, I want to stay freelance! I need the freedom and flexibility. I loose out on these positions because they want someone who will eventually come into the office 9-5. But I feel like if they want to attract those people they should just be advertising a regular job opening, not as a freelance position. This girl isn’t commuting to an office ever again!

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Id have to say this is semi accurate. The only thing I want to point out is that not all freelances require you to sign a 1099 tax form that gives you the full paycheck and makes you owe the IRS. Majority of the freelance I’ve had involved tax forms that I could write 0 and balance my paycheck with the IRS having to owe me. But this is a good advice to consider.