I’m always active, especially mentally. I expect that tost of the time it’s a bit of a nightmare for those around me. I even remember going hiking on my honeymoon as I was bored or doing nothing around a pool. I’m just that type of person.

As such, my mind always needs to be exploring new ideas and learning new things. Even on top of an extremely intense professional working life, I like to do things alongside. The main reasons why fall into three buckets: wealth building, learning skills, retaining skills.

Why I do side hustles

a. To build more income or wealth

An obvious one, i know. It’s why most people get a side hustle. I’m also at a point where my side hustles earn about what I make in my ‘job’, certainly way way more per hour.

b. To learn skills I don’t have yet

I learnt the basics of web development, running an ecommerce site, accounting and cash flow all with side hustles. It may not be really deep or technical, but it’s certainly practical hands-on experience which means I can now drive others in these areas have a better understanding myself.

c. To refine and stay sharp in existing skills

My main functional area is marketing, especially B2B marketing. I live it, I breathe it, day in, day out. Yet, most of this time is at a very high level, strategic, hands-off level. So, how can I stay sharp with what works, the functional nuances and have credible application of these things? Well, my side hustles come in to help. If I want to test something new or go deeper into an evolving area, i’ve got an existing playground to go 🙂

So that is my why’s, but what exactly have i done? Well i warn you, it’ll appear as random as hell initially, but there is actually a sensible story behind most of it… (or so i tell myself being a pretty logical thinker).

Investments excluded

But, before I jump into them I want to be clear, i’m a Director and board member of Ledger Bennett. This is a 50-60 hours week work week, pretty much every week. Side hustlers are on top of that.

Plus, the majority of these side hustles aren’t anything i’d call truly passive investments or real wealth building. At least not when they started! Therefore, it excludes owning property, crypto investments, stock portfolios etc. The side hustles are all the stuff that helps me make these investments.

I’m also not going to go into each one in detail here, i’ve got a separate post outlining the pros and cons of each model, plus a lesson from each one here.

My Side Hustles

  1. DJ – main income, not side hustle (retired ;)) Check me on Spotify if you’d like.
  2. Record Label – business, not side hustle (closed)
  3. Bag hire company – ecommerce side hustle (closed)
  4. Chocolate fountain hire company – cash flow side hustle (sold)
  5. HMO management company – cash flow side hustle (sold)
  6. Property seller lead generation business – cash flow and wealth building side hustle (active)
  7. Property management lead generation site – cash flow and asset building side hustle (active)
  8. Investment affiliate site – cash flow and asset building side hustle (active)
  9. Lead generation site for a niche business – cash flow and asset building side hustle (active)
  10. Marketing software – asset building (active)
  11. Personal brand – cashflow side hustle (active)

Having gone through all of these side hustles, here are my top 6 lessons that i’ve learnt (the hard way).

6 lessons i’ve learnt

1. Side hustles take more time, effort and money than you think

If you’re just looking for extra money quickly from a side hustle, just get a second job or gig. A side hustle that you want to build an income stream (not trade time for money) or an asset takes a lot more time, waaaaay more effort and probably more money to actually get any sort of return. You need to invest significantly upfront (in terms of time or money) before any sort of sales are generated. And even then, scaling also takes time. So don’t expect it to pay back quickly.

This is one of the reasons I really like a few things actively going on all of the time. I can switch focus so don’t get frustrated if results are not coming in quickly. 

2. Look for complimentary add-on streams

Whilst my list looks random, many have been bolt ons to existing hustle streams. Take property as an example. This started as a straight-forward, single let investment and involved into a handful of revenue streams and an exited business.

  1. Bought an initial single let residential investment property. Added a few more.
  2. Wanted to source better investment deals so sorted an online lead generation site.
  3. Bought a few more single lets (which were deal sourced).
  4. Generated a few more leads than I wanted to buy, so packaged them and sold them.
  5. Wanted more cash flow so bought a HMO.
  6. Realised there were no good letting agents, so self-managed the HMO.
  7. Realised other HMO landlords also wanted a management service, so started a HMO management company (both rent-to-rent model and traditional agent model management model for HMOs)
  8. The local market was become more saturated and less profitable, (plus I also had too many other commitments currently on) so exited this business through selling existing management agreements to other agents/service providers.
  9. Retained lead sourcing of HMO management as had good online lead generation in place from the business. Now just package the deals for sale or sell the leads.

These is the steps through private personal investments and 3 side hustles, to which 1 was sold and 2 still active. Looking for opportunities where you have niche knowledge, existing relationships and can easily add a revenue stream is a great way to increase income without all of the heavy lifting being repeated. Yes, there is effort in start the extra item – but it isn’t 100% like starting again, it’s probably closer to 50%.

3. Use experience and skills

For me, side hustles have always been a great test bed to learn, practice and develop new skills. Whilst being a big picture thinker and naturally operating in high level strategy, this only gets you so far without real world experience and practical understanding. It is no good saying to do something, if it won’t actually work. And there is no substitute to being able to test things in the real world.

Starting in a brand new sector AND requiring skills you don’t have today is twice as hard. Not only do you have to learn a new business model, gain industry understanding and grow experience – you also have to develop capabilities at the same time. If you’re transferring skills to another sector then it certainly saves on your ramp-up time. This is just like looking for add-on streams, the further you go from what you know the steeping (and often longer and harder) the time to results are.

As i’ve said before though, for me side hustles are a great way to do exactly this and learn new skills. Just be aware of some of the downsides in doing so.

4. Leverage, outsource, partner

I can’t overstate this enough. Leverage whatever you can to other people. I’ve posted a few times on the benefits of outsourcing in a time management post, and also how I learnt this the hard way.

I’ve already covered that time and effort upfront is considerably higher than anticipated, so it is important that whatever help you can get from others helps. Yes, there is a cash cost to this, but i’d rather take less money and keep (as) time rich as possible! 

If I look across all side hustles, I probably spend under 1 hour a day total across 7 things. This means that most get under 1 hour per week! That time is either on high value, income generating tasks or planning what is required next.

The actual doing is all elsewhere:

  • Someone will write the copy, someone else will publish it to the website. 
  • Any leads will be handled by a virtual assistant or contact centre service. 
  • Leads get automatically forwarded onto the end client. 
  • An assistant does a monthly reconcile on lead volume and issues an invoice.

On some of these hustles, yes, the income is very small. But, when you look at that on a per hour on-going basis and regular cash flow it is still fantastic!

On others, the money may be large chunky numbers and inconsistent. So you need to know you’ll be incurring costs to outsource before revenue hits. 

An overlooked aspect of this is practice of building a team and managing people. Lots of people are craving management experience as it is hurdle to their next career step-up. If you can demonstrate that you’ve put together a handful of freelancers and managed them successful, that is a big tick over someone without any experience.

5. Systemise – early and often

This follows on perfectly from leveraging and outsourcing. To me, systemization falls into two parts:

  • Automation 
  • Manual 

Anything that technology systems can do automatically, build that into the way of business as early as possible. Luckily most small business platforms now have great connectivity to other systems which means lots of tasks can be automated: data flows between systems, publishing to multiple places, management of workflows. Look for anything you’re doing manually today (especially regularly repeated tasks) and see if there is way for it to happen automatically.

If systems cannot automatically do it, then make it as easy as possible for others to support you. Examples may be guidelines around blog publishing or image styles, lead qualification questions or decision trees for query handling. All of these documents help you onboarded others to help support you, plus maintain the quality and consistency in what you do.

6. Focus

The last lesson is one i’d like to share, even though I know it is something I don’t do well 😉

I constantly have new ideas I want to execute against and i’m always feeling like, what if, and that, then this. Having so many things going on is not easy and i’m sure it isn’t the best way of maximise your time and energy. It works for me as the upsides are more than financial, the breadth helps me learn faster in more areas. But it does take time and energy.

So, the lesson here is to focus. Do not do 5 things at once out of the gate. Start one, grow it, system it. And once you’re happy with where it is at, then see what you can add on that compliments it.

What have you learnt in side hustles?

So that is me. 6 lessons i’ve learnt in doing side hustles, but what about you…

What are your biggest lessons from running side hustles?

Or may be what are you looking to learn from starting a new side hustle?