The Fine Line Between Side-Hustling & Working

At what point does a side hustle become like being back at work again?

I've been pondering this subject for the past week or so. In my line of side-hustle, work is a bit like waiting for a bus, you wait for ages for one and then three come along at once. This is exactly what happened during March, I started off the month with a pretty clear diary and my oldest client gave notice that he no longer needed my services anymore. That was a bit of a weird contract anyway as I had contracted out one of my friends to his business so was being paid a commision for doing the invoicing and managing any logistics but other than that, I wasn't doing a great deal to earn my cut. That was my first ever gig as a self-employed man and I have to say, I'll be a little sad to see it go despite the fact it has almost zero to do with what my side-hustle is all about which is me doing the consulting.

I digress.

Regular readers will remember that 2021 is about me banking as much bank as I can before Mrs H decides to get off the corporate hamster wheel (I can feel it, it's getting close). I'm kind of a bit tied down waiting for her and what seems now like an endless lockdown to play out. It's been pretty successful so far and I've locked in what I hope will be a few years passive income from redeploying my consulting fees back into investments. We still have a gap in our net worth versus what we need to live fully retired, and when Mrs H's salary stops, that will create a little more pressure as we'll be actually drawing down every penny we spend from our investment income.

So it's fair to say I've been putting myself out there a bit more and that has resulted in a sudden flurry of paid opportunities which is great right?

Or is it?

I worked in my field of expertise for over 20 years and I loved it at the time but whilst I think I'm still pretty good at it, it's pretty difficult to get excited about. I guess you would say it's formulaic for me now. Fortunately it pays really well on the consultancy side so whilst I don't hate doing it, the primary motivation definitely is thinking about the stacking Leopards (the south african version of stacking Benjamins)

The last two weeks have seen me pretty much working full time, juggling a couple of projects. Luckily one was for the UK and one was for the US so I was able to use the time zones to my advantage and service both clients from opposite ends of the day. I was exhausted by the Easter weekend and was glad of the long break.

But this is definitely not a poor little me post, I'm not afraid of hard work and I take pride in exceeding my clients expectations no matter what it takes. The moral of this story is that after being retired for almost a year (2 weeks to go until my freedom anniversary, woohoo!) this spell of full time work has given me a massive flashback to corporate life and how much I've changed since I was a corporate wage slave.

The first thing I noticed was the onset of anxiety from having accountability for what have been some pretty big projects. It's like a being just slightly on edge the whole time. I catch myself thinking about the projects while I'm trying to get to sleep at night. I've actually started sleeping a little less well and I've gone from waking up at 8am and lying in bed until 9am reading the news to walking up at 6:30am and immediately start thinking about what meetings I have and what I need to get completed throughout the day.

It's not great but it's scary to think that I spent close to 20 years in senior leadership positions feeling like that constantly, so much so I didn't even really notice that it made me feel that way at the time. Now that I've been out of the race for a year, I am hypersensitive to the changes in how I'm feeling both mentally and physically and I've only done a couple of weeks at a fairly pedestrian pace compared to some of the hectic situations I use to find myself in constantly.

What has been really eye-opening though is that for the first time in my entire 45 years on this planet, I would actually consider not doing paid work in favour of doing what I do on days I'm not working. If I said that to anyone who knows me well, they would probably say: "Who are you and what have you done with Mr H?"

I guess what I'm saying is in the still relatively short time I haven't been working for the man I have become a significantly more relaxed hooman. I tried to think of an appropriate word to describe it and I guess the best word would be "contented".

Now I'm not quite at the point where I can put up the closed sign on my side hustle as we pushed the FIRE button about 2 years before I should if I measure against the famous 4% drawdown rule. I do really need to keep seizing the opportunities when they present themselves but I'm actually quite pleased that I'm seeing the world differently now, I might actually be growing up, who knew?

But I have started the thought process on where the happy medium is for anyone that is considering pushing the FIRE button and quitting their nice safe well paid job without much of a plan (which is pretty much what I did a year ago). An adventure I highly recommend and one I wish I had done 10 years ago.

So my thought process so far is there are pretty much two types of side hustle:

1. The ones that pay well - Where money is the objective

2. The ones you love doing - Where money is a byproduct

If you can find one that ticks both boxes, grab it with both hands and read no further, you're living the dream.

Then there is time. In my position, Mrs H is working all week so weekend side-hustling is out (unless it's something we do together) so that leaves five days. After dark is also family time and I've never been much of a morning person so lets narrow the window to 9am to 5pm Monday to Friday as the workable shift, or 40 hours for the purpose of the math. Now you can't do the full 5 days as then you're not retired, you're self employed, so has to be half or less of that time or your just part-time self employed which is almost the definition of a side hustle but not quite.

So we've boiled things down to 20ish hours. The question is when, and there's few options there:

1. 2 Days On, 5 Days Off - Knock in your pan for 10 hours over 2 days and then do you for the other 5

2. 4 Half Days? - Maybe Monday to Thursday 9am to 2pm

3. Weekday Mornings? - Eat breakfast at the laptop and do 8-12?

4. Every other day - 7 hours Monday, 7 hours Wednesday & 6 on Friday

5. 20 hours flexitime spread throughout the week

Now if you're anything like me, number 5 jumps straight out at you.

Don't do it, it's a trap!

This is how I got into my current predicament. After 20 years at the grindstone I probably averaged at least 50 and at worst 70 hours per working week. Even through my contract was for 37. People with a work ethic will never work to a fixed set of hours, we work until the job is done.

And this is the nub of it, the more I sit at this machine and earn money, the easier it is to sit at this machine and earn money. I have to break the cycle or I may as well go back to an office job (assuming they still exist in a post-covid era).

So I think once I finish the projects I currently have on my plate I'm actually going to force myself into option 3. I'll start the day with work and log off at 12pm every day. Clearly I'll have to work around my clients but as working principle, it's business in the morning and pleasure in the afternoon for Mr H and however the week pans out, its 21 hours max as that would be the equivalent of 3 working days when you subtract a lunch break and a coffee stop or two.

Most importantly, I think I'm going to put a hard stop on the side hustles I do purely for income (as opposed to for enjoyment) on the 30th April 2023. That will be the third anniversary of my retirement which is how long I always felt I'd be relevant for.

This has turned out be a bit of a rambling post more about how I'm thinking and feeling at the moment but I'm sharing it because it's something I wish I'd thought more about when I was on my FIRE journey. I kinda knew I could do some consulting but I didn't think I would get so much of it nor did I think I'd get to a point so quickly that I'd actually prefer not to do it.

I think the advice that is buried somewhere in this for anyone on the journey to FIRE is less about if you will be able to make money side-hustling and more about how fulfilling what you have to do to earn money is.

I definitely need to give this some more thought but I think I need to give a lot more attention to a side-hustle I can truly get excited about than one that make it rain with cash. Maybe there is one that can do both and can be done in less than 20 hours per week? If you have any great ideas (keep it clean people!) let me know your view in the comments. I think I'm going to need help on this one.

Until next time, keep living