How I replaced my day job income in 90 days

How I replaced my day job income in 90 days

May 16th was the last day at my day job, almost exactly three months ago. When I left, my salary was $47,500, which converted to a take-home pay of about $3,300 a month. My projected income for August is roughly $3,700…which means that, come end of August, I should have replaced or exceeded my day job income within three months of going back to freelancing. And I’ve got some pretty solid guesses as to what did it – so I’ve got four tips for you. The last one is the most important one, so make sure you read to the end!

Have something “pitchable”

Part of my theory on what has made such a big difference this time around vs. doing project management/systems consulting work is that writing is a lot more pitchable than project management. People want project management – they want the end result – but they don’t really understand what it is and it’s not very concrete, which oftentimes means that they want don’t to pay for it. Writing is way more tangible, so it’s more pitchable.

Ideally, yeah, you’ll have people coming to you through referrals and as a result of your own marketing, but you can’t always rely on that, especially when you’re just starting out. If you’re a service based professional that isn’t pitchable, think about creating some kind of product that is:

  • high quality
  • which doesn’t necessarily mean complicated – but don’t just spend five minutes on a PDF and then charge $147 for it
  • answers someones’ questions or serves a need
  • and is easily promoteable

It won’t be passive income, but having even a few small products for sale can bolster income – my planners were invaluable for that when I first created them.


Set up IFTTT triggers, as described in this post. And then, whatever else you do on a given day, make sure that you pitch yourself for 3-5 things that are open job/proposal/gig requests. And if you can or want to, another 3-5 things a week that aren’t open requests – whether that’s emailing agencies to see if they need designers, talking to local marketing firms to see if they have a need for contract work, etc. Even if your service isn’t as “pitchable” as writing or designing or coding, you can still get a much clearer view on peoples’ needs/wants/what they’re willing to pay for by just talking to a lot of people – this is the whole basis of Shenee’s 100 People Project.

Being this proactive is honestly, pretty uncomfortable. It can feel by turns hectic and disheartening juggling it on top of a day job’s workload (and not hearing back on probably half or more of what you send in your information for). But you’ve got to get comfortable with it and I don’t know of any better way to do so than just acknowledging it’s going to be uncomfy, actively throwing yourself into it anyways, and making it a numbers game (as in, I’m doing this many pitches today, and then I’m done and I’m not going to think about it any more).

Plan ahead

In my case, this was pitching proactively (as described above), starting at about six weeks out. I was lucky in that I’ve been writing online since 2008, so I could just jump straight to pitching without having to worry too much about building up a portfolio.

In your case, if you’re currently lacking a portfolio, you’ll want to be pitching yourself and building a portfolio. If your portfolio is currently looking a bit thin, try adding:

  • designs (or whatever) that you did for yourself, not for a client
  • pulling together work from your current clients (at the day job or not – depending on how strict your employment contract is as far as NDAs and whatnot)
  • adding in other work as you get it and/or taking on a very small amount of beta clients as portfolio builders (this needs to be carefully navigated so you don’t wind up with cheapskate PITA clients)

And the last secret: it didn’t take 90 days, it took five freakin’ years

Can you do this, too? Is it possible? Yes.

But there are so many people blowing smoke out their ass on the internet about “X days to ONE MEEEELLION DOLLARS” and here’s the thing, guys: I have been doing this (“this” = some variation of self employment, freelancing, or entrepreneurship) for over five years now.

For the first three years, I had no idea if I was going to make $500 or $1000 or $2000 in a month. (And oftentimes, it was a lot closer to $500 than anything else.) If it wasn’t for my then-husband’s income and both of our family’s support, we would have been homeless multiple times over. I had not one but three nervous breakdowns last year because of my absolute bullheaded refusal to see what was working, what wasn’t, and change my business strategy and offerings accordingly.

We want an overnight success story because it’s fun and inspiring and sexy, but at the same time, it’s so easy to beat ourselves up when we can’t match it. And that’s because they’re just that: STORIES. So fucking many of the people who seem to have exploded “overnight” on the internet had (extensive) previous business experience or a strong network of fellow entrepreneurs with followings to help them kickstart their business, or both. And we forget that. (Or are, deliberately or not, misled into not realizing that.) 

I don’t ever want to play into this false mythology of the bootstrapped entrepreneur that started a business and six months later is lying on a beach somewhere exotic drinking mai tais. (I’m more of a margarita girl anyways. Though I’ve been really into bloody marys lately.) 

Yes. I replaced my day job income in 90 days. I also had these things on my side:

  • products to sell
  • an email list of 800+ people who already know and (I think mostly) like me
  • a solid social media audience
  • business friends and connections
  • a decent sized portfolio
  • and that previously mentioned insane bullheadedness

This is NOT to say you can’t replace your day job income in 90 days.

I’m not here to pee on your parade. Quality work and the willingness to be ridiculously proactive (and, you know, objectively assess your strategy when something isn’t working) can do a lot.

It IS to say that I don’t want anyone to beat themselves up over unattainable business goals. Just like I’m sick of photoshopped bullshit in our magazines making people feel bad about an ideal that is literally physically unattainable, I’m sick of stories that highlight the good and gloss over the bad. 

Is it worth it?

I honestly don’t know. I don’t know how to quantify that. I know that I love the freedom. I know that I love the work I’m doing. I know that I love interacting with people and hearing how something I wrote or made or taught changed things for them. I also know that my body probably could have done without those three nervous breakdowns last year.

Am I glad I’ve stuck with it? Yes. Was it easy? Hell no. Was it fun? A lot of the time.

So there you have it.

That’s my “overnight success” story that was five years in the making. My suspicion is that now that I have a decent client base and some momentum built up, the next five years will be a lot easier than the first five. My other suspicion is that, really, it’s less about having business acumen than it is about just sticking it out long enough. Make of that what you will. And may the odds be ever in your favor.

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