midnight hustling with piper of one sydney road

Thank you so much for the great response to this new Midnight Hustler series! I’m excited to expand on this aspect of “designing a life with intention” more in the upcoming months.

Today I have picked our very own Dream Reporter‘s brain for her story on jumping the corporate ship to start One Sydney Road full-time. Piper is a recent alumni of the Midnight Hustling crowd, so her experiences are from the not-so-distant past and her actions might definitely be applicable for a lot of other Midnight Hustlers out there.


When you first got really serious about launching your companies full-time and were still working your day job, what fears did you have about making the shift? How did you overcome those fears?

The better question is “what fears didn’t I have?!” Of course, the main one was “how do I take the leap in this economy – who leaves their job?” and “am I crazy?”  (ok, don’t answer that!)  Another fear was that creeping doubt as to whether I could actually run my own business and earn a living from it.  Although I had spent years researching and even got my degree in Entrepreneurship – reality is much different than that cozy, wonderful dream world!  The constant question nagging me was “could I really do this – what if I don’t have enough experience or know-how?”

I got over the fear in a few ways (and by no means is it gone forever – the fear definitely creeps up still – I just have more ways to deal with the little monster now and I’m refusing to let it have the final say – just because I’m feeling scared, doesn’t mean I get to use that as an excuse to not pursue my dream!)  The first thing I did was get my finances in order and really look at what I would need to bring in if I was to leave my job, how long could we survive, do we have enough savings – I think the more you know the answers to these questions (even if the answers aren’t pretty!), the more you can figure out how to get from point A to point B.  It might take some time (and trust me, patience is not my strong suit!!)  But knowing it’ll take 1 year to save up versus “who knows when” is a hell of a lot better!!

The other thing for me was more personal.  My mother, who was my role model & best friend, died at the young age of 62.  Boy, does that make you realize how short life truly is – and I knew I didn’t want to spend another moment of it feeling miserable and not pursuing my passion.  Nothing helps get you past that fear than realizing that you only have one life to live and you best make it a good one!!

How did you structure your day balancing both your job and your growing business/blog? Did it require any sacrifices?

I wish I could say it was easy -  but the honest answer is that it was a lot of work and did require some sacrifices.  On the same hand, I wouldn’t trade it for anything because I was doing something I was passionate about and knew there was a bigger picture to consider.  I was somewhat lucky that my day job didn’t keep me busy enough.  This gave me some extra time to work on my store.  Unfortunately I couldn’t really consider this quality working time – not when you constantly have to switch your screen when someone walks past your desk so they don’t see that you’re on the internet.  Or not being able to listen to music and lay out all my inspiration files on my desk to get creative and inspired.  Plus our access on the internet was blocked for a good chunk of sites that I needed to visit!

So basically this required me to get organized – I created a to-do list that had a section titled “Work to be done at home” and another titled “Work to be done at work”.  Every night I would break up this list into what could be feasibly done at work – anything that couldn’t, meant I would have to come home and work on those items.  I would only schedule a lunch break one or 2 times a week – instead choosing to work on my business through lunch.

And yes, you guessed it, it meant lots of LONG hours once I got home.  I would get home around 4:30pm and would almost immediately get on the computer and work until 9 or 10 at night – every night.  Weekends were no longer that – they were just days where I didn’t have to go in to my day job and could spend both days getting things done on my own business.  (this was actually a bigger sacrifice and took some time getting used to because at the same time I started working weekends on the business, my hubby, who worked weekends for years, was finally in a position to work just normal Mon-Fri work days!!  Figures, right?!)  Again, it was focusing on the big picture that helped me get through this!

How did you select your quit date and how did your company respond to the decision? Were they surprised? Where they supportive?

Ah, the quit date!!  I seriously, over the years, have had a bunch of quit dates – I used these as ways to get through the misery of working my day job – “only 3 months and I can quit”!  Of course this was just a psychological game I played with myself to pretend that I could actually leave at any time!  Then when I was actually working on starting my store, I would set a quit date for say 4 months in the future and when that date showed up and I was nowhere near ready (as in, no website, no products) I’d just set a new one (pretty sure I had about 4 quit dates!)  This went on for way too long.  It took signing on with a web designer & getting a “go live” date to really get serious about an actual quit date. I realized pretty quickly that there was no way I could give 110% to my business if I was still working full time.  So I set my non-fake actual quit date!  And lucky for me, my boss and co-workers were very supportive.

What is the best piece of advice you wish you had before you started your midnight hustling to have a smoother transition to self-employment?

Some of the best advice I received revolved around the same thing – listen to your instinct, your gut.  I constantly would try and quiet my gut (and not just by eating!)  But the more I listened, the louder it got.  It started as some quiet murmuring about how dissatisfied I was at my day job and how there has to be something better.  Then it just got louder and louder over time until it was absolutely shouting at me (and trust me, I still kept trying to not listen – but boy can my gut get loud!)   That’s when I realized my instinct was telling me it was time to take the leap and work on my business full time – that I was ready for the challenge. I think our instinct knows more than we give it credit for!

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  1. Maggie Rose

    Thanks Piper for sharing! I’ve never heard of splitting a to-do list into places, but it makes total sense! If I have any flexible time at work I feel like I should be using it (beyond just checking email, social media, etc) but I don’t usually have tasks organized enough to do that (or my notebook is at home). Thanks for that tip, and congratulations again!

  2. Lauren

    Another great interview and inspiration!! Thank you for sharing – you have no idea how extremely helpful these are!!

  3. Brandi

    This is such a fantastic interview with Piper. I think she went through what many people who are considering starting their own business go through. What an inspiration!

  4. lou

    what an inspiration. and how well i already know those disappearing weekends and working long hours at home after the regular job and i’m nowhere near a quit date. can’t mention enough how brave you are.

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