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Want To Work for Yourself? First You Need to Know Yourself.

Whether you’re starting a side-hustle, want to open a brick-and-mortar store, or want to shift from freelance to business owner, I think one of the most important things you need to focus on when you work for yourself is knowing yourself.

There are so many incredible resources on the internet that can help you with the many (many!) elements involved in self-employment, but how do you decide what advice to follow and what to ignore?

Diving into your personal preferences, strengths and weaknesses, values, and priorities, will help you decide which voices to listen to and which to ignore. It can also help you create decision filters for small and big decisions: whether to open that email or whether to hire an assistant.

Since I was a teenager, I’ve always known that I wanted to work for myself. When I actually took the leap in my late twenties all I knew was that I wanted to have more control over who I worked with and that I needed to make some money, fast. My financial circumstances at the time resulted in me needing to zero in on making my business successful and make sacrifices in other areas of life so I could turn the hustle into financial stability.

But, I still felt like I was flailing, thrashing around trying to figure out how to build a work life that was sustainable both financially and personally.

One of the many things that brought about an important turning point for me was when I finally let go of the internal pressure to do what “everyone else” was doing and really spent time to get clarity on what I wanted. Then I had to give myself permission to actually do what I wanted and trust my gut.

Did I want to use social media to get new clients? Nope. Did I want to sacrifice quality to scale really fast just because there was a demand for my services? Nope. Could I be making more money if I did X, Y, and Z? Definitely. Did I want to do X, Y, and Z? Nope.

There is always more you could be doing when it comes to working for yourself. At some point you have to give yourself permission to stop and say, “this is enough.” And I think the only way to know what “enough” should look like for you is to pay attention and use the process to grow  in self-awareness.  

I’m an avid journaler so that’s how I regularly reflect on my work life. If you’re not into journaling you could add a monthly reflection into your routine, get a business coach or mentor, join an online community for freelancers, or meet regularly with a business buddy in person or on Skype to verbally process what’s working and what’s not.

Here are some questions to ask yourself if you’re starting out on your self-employment journey:

1. Do you really want to work for yourself? Or do you just want more flexibility?

2. Do you like working alone or do you work best collaborating with a team?

3. What helps you make confident decisions?

4. Do you enjoy wearing lots of “hats” or do you need to prioritize setting money aside so that you can pay other professionals to do the parts you don’t like?

5. What’s your tolerance for risk? If it’s low, how can you plan ahead to reduce risk? If it’s high, how can you set some parameters in place so that you don’t take risks for their own sake or make any impulsive decisions?

6. Do you need accountability to get things done? How will you set up accountability for tasks that don’t already have exterior accountability (like a client deadline).

7. Do you struggle with procrastination or perfectionism? How are you going to protect yourself from letting these habits take over?

8. What are the biggest things that have caused you stress in your work life? Are they habits of your own that can be changed (like obviously procrastinating and doing work at the last second is stressful)? Or were they related to interpersonal challenges with other people?  

Let me state what I hope is obvious: it’s okay to not know all the answers to these questions when you begin. This is not an exhaustive list. But if you need permission to ignore some standard business advice, take things slowly, take a big risk, or pivot, I’m here cheering you on. One of the things I have enjoyed most about working for myself is the level of self-insight I have gained through the years. It feels so satisfying to know what I need to thrive and know how to create a business that is sustainable and worth it for me. 

P.S. Here are some great business-related podcasts I’ve enjoyed on my own self-employment journey. I don’t currently listen to all of these because I just don’t have the time, but they have all been extremely helpful or valuable to me in different seasons:

• Listen to the podcast episode about this post

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  1. KC

    I’d add: is it really *you* wanting to start a business or is it more because that’s the thing to do – it’s what all the cool/artsy/”successful” people are doing? And if having your own business would mostly be a way to indulge in your love of fancy office supplies and logo design and increase your feelings of importance, then maybe think twice? Having your own company business cards that are exactly how you’d like them to be can definitely be a rush, but that rush will not get you very far into things like invoicing or taxes or advertising or cold-calling (or whatever inescapable not-your-jam business activities come with your business).

    I’ve been boggled at how incredibly standard it is for people to enthuse, if they’re at all pleased with the outcomes of your hobby, that you should definitely turn it into a business (even if it’s something like knitting, where no, you are not likely to get paid even a dollar an hour to knit custom socks for people). Not every hobby needs to be profitable; sometimes we can have hobbies that just refresh us and enrich our lives, and they’re not valueless because they’re not financially remunerative, and keeping them as hobbies is not a failure.

    (but small businesses are awesome, and if you can deal with the feast-and-famine and the “oh, wait, there’s what I intend to do for a living and then there’s all this paperwork to deal with as well” side and all the rest of the bland/irritating/non-dramatic aspects that are rarely prominent in Successful Small Business interviews, it can be great! Just… know yourself and know what you’re getting into, and know that it is not an example of personal inadequacy to have a 9-5 paying job that you don’t particularly like but at least don’t detest, paired with a rest-of-life [hobbies, relationships, volunteering, etc.] that you enjoy.)

  2. Beth

    I think this is a great article! My husband has been working from home (for himself) more or less for the last two years (writing and translating). I’m a stay at home mom. One thing he mentioned yesterday was that he mostly liked what he was doing but he missed the camaraderie of having coworkers. He tells me what he’s working on but it’s not quite the same as having people next to you who really “get” what you’re doing and have the same interest in it or the same complaints with it, etc. He’s an introvert so he doesn’t miss it every day but having someone who’s a “professional” friend would be nice for him.

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