Kissing The w2 Life Goodbye – 4 Things You Need To Know About the 1099 Life (Working For Yourself)


After my divorce, the importance of having a standard 9-5 diminished because with it came demands that no longer had space in my life.  While married I was able to throw myself into my work and deal with being on call, late night emails and text messages and it was OK back then.

At this point in my life, my perspective has changed and I want to leave work at work.  I want to be able to attend Bible study on certain days, work out in the mornings and have the flexibility to attend to life issues as they come up without having to worry about how many sick or vacation days I have left or having someone dock my pay if I come in 6 minutes late due to beltway traffic.

Overall, I just needed to take my time back and own it while utilizing it on my terms.  So I did.  I made the jump which involves working for myself.  I am a full time blogger, freelancer and psychotherapist in private practice.  And I love it.  I own my time and control when I come and go.  That’s important to me.

Welcome to the 1099 life.

Luckily, having multiple streams of income means having options and it felt good not being tied to a job because of money.  That’s called financial slavery and having a stash saved me a few times so I’m thankful for my money hoarding tendencies.  But not having a regular paycheck means having to budget in ways that I hadn’t previously thought of.  And I’d be lying if I didn’t admit to the fact that having to change how I budget and pay bills can be unnerving at times.

There’s no set time for a paycheck (1st and the 15th anyone?) as payments for various invoices come in at different times of the month.  Still, I am thankful that I don’t have to chase down invoices for payment so that works in my favor.  So here’s how I pay my bills on time while adjusting to the new 1099 life.  Some I’ve utilized, some I have not so let me know what works for you if you don’t see it on this list:

Create A Cushion

Let’s say your monthly expenses and obligations are $2000 for the month.  Find a way to save that amount ahead of time to create a cushion for yourself.  As your invoices and payments come in then you rebuild the cushion in preparation for the next month’s obligations.  Make sense?  You can also pull this amount from savings and then replace it as the payments come in.  Everyone’s situation is different so there is no one size fits all.

Change Due Dates

If you know that your largest invoice payments comes in on the 18th of the month but your cell phone bill is due on the 7th then you should call the cell phone company to ask about shifting your due date.  Do this for any and all accounts that you can so that you give yourself space to receive  and send out payments.  This may involve you paying the next month ahead of time but it’s well worth it to avoid late charges because you haven’t received payment yet.

Budget And Pay As You Go

Let’s be realistic.  If you are receiving payments sporadically throughout the month then you’ll need to adopt a strategy that allows you to pay your bills on time.  You should know specifically how much money you’ll need for the month and pay your obligations from your cushion or pay them as you receive payments.  As you pay each bill then you check it off as you move throughout the month.  As a W2 employee with a steady paycheck, literally every bill was pay between the 1st and the 4th of the month.

If all of your invoice payments aren’t in by that time then paying as you go may work.  This will require you to pay more attention to your bank account for deposits and checking your calendar to make sure that you’re on top of things in this regard.

Float Payments

If you’re in a bind and your invoices are late, sit down and decide which obligations can be floated until the end of the month or next month.  Call and talk to your creditors so that they know when to expect payment while noting your account.  This is typically OK for utility bills such as light, gas or cable since they usually combine the bills.  DO NOT abuse this option.  Do this as a last resort because this can get you in trouble if you float the bill a few too many times, especially consecutively.

Every 1099er does things differently so how I do this may be different from others so I’m interested to hear how others handle the 1099 life.  Yes, it can be unnerving but if freedom is important to you then JUST DO IT.  With proper planning of course!  My only regret is not making the jump sooner because I’d be farther along than I am now.  In the end, I value having control over my time and work and it’s an awesome feeling to be able to control this aspect of my life.

  • yessu

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  • Fiona-

    I find working for myself liberating and I love the flexibility. For me having come from the safety o corporate life it was a huge change requiring discipline and cashew management, but fortunately the business model I work with is low in operating costs and delivers a six figure income. I think I have found the best business venture where I am in on troll and loving the lifestyle as well!


    I’m in the same boat. I’ve gone out on my own and will be working my way through “what” I can spend and “when” – which is scary. Like everyone, in order to drive business I need to promote myself and that is a nebulous assumed expense. Where will I fit that cost in? At what point will I even consider expenses vs. starting a stash?

    It may sound a little odd but, I’m looking forward to having to pay taxes because that’s an indicator that I’m succeeding. I will be watching and reading this component of your blog like a hawk – a fiscal, stiletto talloned hawk!

    Thank you Ginger AND good luck to you Nikki and Maria as well!

  • Maria (

    This was an awesome post! As a new entrepreneur, I’ve been considering how to work this out. I currently have a cushion to live off but was considering what to do as I try to live off of eventual business income. Thanks!!

  • Nikki

    I LOVE your blog :) I too am I a psychotherapist… (newbie) and I also work part time as a social worker. Next years tax season will be interesting because I’ll have to use 1099 and W2. Im excited to build my clientele up and I have decided that I’ll pay all of my bills with my steady income and I’ll use my therapy income for misc things, saving, and ME :)

    • Ginger-GirlsJustWannaHaveFunds

      Thanks Nikki! That sounds like a great plan! I’ve thought about going back to the W2 life and may do that depending on the opp – but for now freedom to control my time works best for me. Let me know if you ever want to talk shop, I love connecting with other therapists in the field. Talk soon!