Side Hustle University

Chapter One:  Understanding Your WHY

As we stated above, everyone has their own reason why they might want to pick up a side hustle — and not everyone’s reasons are the same. It is crucial to identify exactly WHY you want to start a side hustle, as this will help guide you in the steps to come.

How to identify your WHY (and what to do once you have)

You might be one of the lucky few who already knows exactly what you want to do, and why you want to do it. For the rest of us mortals, a little more digging is required. Uncovering our own personal motivations and priorities can be tricky, and a lot of times what we THINK we want (and WHY we think we want it) is really only a surface level observation. Truly understanding ourselves takes a lot of time, patience, and introspection.

Priorities vs goals: What’s the difference?

There may be a fine line between priorities and goals, but the difference is there. Here’s the dictionary definition for you word nerds out there:

Priority (n): A thing that is regarded more important than another.

Goal (n): The object of a person’s ambition or effort; an aim or desired result.

Put simply, a priority is a facet of your life that is particularly important to you, whereas a goal is something you would like to achieve. For example, spending time with your family might be a priority. Making enough income from your side hustle to replace your full time job — and therefore be able to work from home and spend more time with your family — is a goal. Goals can be priorities, and (like in the example above) they can certainly be complementary.

This distinction matters simply because you will need to identify and evaluate both before you get started with the real grunt work of choosing and launching your side hustle.

How to uncover your personal priorities

So how exactly do you uncover your priorities if you don’t already know what they are? Go ahead and grab a pen or pencil and a pad of paper and hold on tight, because it’s going to be a bumpy ride. No one ever said that introspection was easy, right?

1) Identify the “categories” in your life

The first thing you will want to do is sort your life into neat little categories. But my life is a mess, you say? Don’t worry. Ours too. The good thing is, you don’t have to have your stuff together to complete this exercise. If you are human (and we’re guessing you are), chances are you will have some amount of chaos in your day-to-day, but that doesn’t mean that your life doesn’t break down into some very specific sections. Your categories might look a little like this: Family, Friends, Work, Hobby 1, Hobby 2, That Netflix Series You are Currently Binging, Eat, Sleep … you get the point. Make the list as long as you like, and be as specific as you want. We will come back to it later.

2) Name your values

The next thing you will want to do is list your values. This may take a bit more digging than the step above, but that’s okay. Feel free to take your time and really consider what is important to you, what you stand for, and what you believe in.

3) What things can you not live without?

Next, list the things in life that you know you can’t live with out. This list might end up a lot shallower than your values list, and that’s okay. If you absolutely can’t live without nice clothes, or a meal out every now and then, go ahead and put it down. The more honest you are with yourself, the easier it will be to pick your perfect side hustle and avoid disappointment.

4) Ask yourself the hard questions

Once you have made the lists above, it is time compare them and ask yourself some questions. This will help you rate the priorities you have identified and uncover which ones are truly the most important to you. Here is a (non-exhaustive) list of some questions you might want to ask yourself:

  • Why do I spend my days the way I do?
  • Why are these values important to me?
  • Do I need the things I identified in step three? Why or why not? If I don’t need them, why do I want them? Would I be genuinely unhappy without these things in my life?
  • What could I live without in the three lists I made?
  • If I had to give up everything, what would be the hardest thing to let go of? If I could keep just one thing, what would it be?

The goal of these questions is to eventually break the elements in your life down into must-haves, wants, and could-live-withouts. Ideally, you should have a list of your top-five (or so) priorities when you are done.

5) Describe your ideal day (and your ideal life)

After you have completed all of the above steps, it is time to put on your creative thinking cap and do a little daydreaming. The goal of this exercise? To image your ideal day and identify the elements within it. After you’ve walked through your “perfect day” scenario, go ahead and expand on it. What would your life be like if it looked exactly how you wanted it to? Don’t be afraid to dream big or be a bit impractical.

Write these things down, and then compare it with the priorities you identified above. Is it in line with them? If the answer is yes, then you’ve done your job well. If your answer is no, however, you might want to go back through the steps above and work out what you might have missed. This exercise can help you identify whether or not your priorities are in line with the life you want to live.

Discovering your goals

After you have identified your priorities, it is time to take a look at your goals. As we said before, your goals are those things that you are working towards in your life — they are something concrete that you desire to achieve. Maybe you want to buy a house in five years. That’s a goal. Maybe you want to increase your earnings by a specific amount, finish a project, or travel somewhere new. Those are goals as well. Take some time to think about the things you want to achieve and write them down. Do they align with your priorities? Are there things in your life you will need to change to reach them successfully? Are some of your goals priorities themselves? You will take all of this into account when picking your side hustle.

Personal constraints  

The next thing you will want to consider is your personal constraints. A personal constraint is something in your life that limits you in some way and is generally uncontrollable. For example, being the primary caregiver for a child might place a constraint on the amount of time you can spend on your side hustle, while having a low-paying day job may place a constraint on how much money you can put into a potential side hustle.

Identifying and accepting your constraints  

Identifying your constraints starts the same way as identifying your goals and priorities — with a simple list. Here are some questions that may help you identify your constraints.

  • What factors do I have in my life that I can’t control? 
  • What obligations do I currently have? 
  • Do I have any illnesses or health conditions that limit my energy, mood, or time? 
  • Do I have young, elderly, or sick family members that need my care? 
  • What is my current schedule like, and how much control do I have over it?

It is important to be brutally honest with yourself during this process. The better you identify your constraints and come to terms with them, the more prepared you will be to choose your side hustle. 

Sometimes it takes a little bit of time to accept the constraints in your life — particularly if they are difficult and unasked for. If you are struggling, make sure you reach out to your friends and family. You don’t have to do this alone — nor should you.

Working with what you have 

The first step towards accepting your constraints is identifying what they are. The second step is finding ways to work around them.

Your limitations don’t have to define you, and the things you can’t control don’t need to stop you from doing the things you desire. A little creativity goes a long way — you just need to be willing to compromise and understand that somethings might not look exactly the way you originally envisioned. Need inspiration? Here is an example of a common constraint and ways to work around it.

Example :

Problem: You are a parent and the primary caregiver of one (or more) young children who demand a lot of your time. Scheduling can be difficult because you rarely what to expect on any given day, and you when you do have free time, you are exhausted.

Solution: First, make sure you are getting enough rest, eating well, and taking the time to exercise, as all of these things can improve your energy levels. After you’ve seen to that, try scheduling time each week to work on your side hustle. Maybe you can ask someone to watch the kids for an hour every Tuesday (or whenever). Nap time is also a great time to get a little work in, and (if you’re not too tired) mornings before the kids have woken up, or evenings after they have gone to bed can also be good times to get your hustle on. Another strategy is to think of things that you can do while the kids are awake and crazy. You can also pick a project you would like to work on throughout the day, and keep it open on your desk to come back to whenever you get a spare minute.

Your WHY

After you have completed the above exercises, you should have a solid understanding of what you want out of life, why you want it, and how you are going to achieve it. You should also have a good grasp on those things in your life that you will need to work around. 

Your “why” — your reason for doing the things you do, and your reason for starting up a side hustle — comes from a combination of all these elements we have discussed. Your “why” is a conglomeration of your goals and your priorities, but is also affected strongly by the constraints you have in your life.

The power of writing it down

Once you have discovered your “why,” take the time to write it out in a few concise sentences. Writing it down — like a contract, of sorts — is an incredibly powerful way to make goals, and priorities feel more real. Don’t be afraid to post this “contract” somewhere where you will see it — ideally in your home office, or where ever you plan to do your work.


Hopefully, after walking through the steps in this chapter, you have a better idea of what makes you tick. Moving on, you will use this knowledge to help you through the process of picking your side hustle and eventually, you will use it to find encouragement and motivation when you are struggling through a tough spot on your side hustle journey.