Jan. 1, 2021

3 Things to ask yourself before going self-employed

3 Things to ask yourself before going self-employed

💯💯💯 "You're not just a photographer, you're also sales, your marketing, your the legal department, accounting, r&d, customer service, the list goes on, you don't have anybody to pass the buck to. So I asked you How comfortable are you taking the time to learn things like intellectual property so that you can educate your clients on the appropriate usage? How comfortable are you negotiating terms on a contract or preparing an estimate or trying to collect on delinquent payments? This not only takes time to learn, it takes time to execute as well."

The move to self-employment comes with some amazing benefits but it isn't a decision to be made lightly.  There are no educational or financial requirements for one to meet before branching off on your own.  There isn't even a required amount of experience before pursuing one's own business.  So how are we supposed to know when we are ready?  Consider asking yourself the following 3 questions if you're complementing this move.

  1. Am I ok with uncertainty?
  2. Am I ok with shooting 10% of the time?
  3. Am I being 'pushed' or am I being 'pulled' into self-employment?

In this episode, we'll dive into what these questions shed light on in your decision-making process so that you can live your best creative life. 


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There comes a time in every freelancers career when they think to themselves, "should I go all in on this? Or should I just maintain the status quo and keep my job and freelance on the side?"  Whether you've been dabbling in freelancing for six months or six years, part of you might be curious in how your life would play out if you took the leap into full-time self-employment, when is the right time for you to take that plunge? What should I be asking myself to gauge whether or not I'm ready. Now, here's what makes this notion so difficult to universally advise people on there aren't many hard and fast rules that definitively say this is the right time to venture out on your own. First of all, the parameters for entry into your creative field are rarely met with rigid standards the way a medical or legal profession would. There's no law that states you need this degree, or this many hours to practice your art. Likewise, if you want it to become self-employed, there's no construct that states you need to have this educational standing, or be of this age or have this much experience with this much money in your bank account. My scenario is going to be different than yours, and yours will be different from the next person's. 

Now to help us out here, I'm going to use an analogy given to me by a friend who has spent his entire life around the sport of boxing. And this analogy has stayed with me when I think about the topic of venturing off onto your own. He said in order to even entertain the idea of training someone in the sport of boxing, in order to even entertain the notion of stepping into the ring, you're gonna have to be okay with three basic principles. Number one, you have to be okay with taking a beating. If you're not okay with that, stop right now, go pick up something else, go pick up golf. Number two, you have to be okay, giving a beating. If you're not, stop right now, go pick up tennis, go pick up bocce ball. And number three, you're gonna have to be okay, with repetition. You will be hammering muscle memory for a long time. And if the thought of that drives you absolutely mad, stop right now, go pick up something less demanding. And so this analogy got me to thinking about my own boxing ring, which is the freelancing ecosystem. What do I think are the prerequisites? So I've written down three basic questions to gauge whether this is the right move for you to be independent. 

So question number one, are you okay with uncertainty? freelancing is filled with uncertainty, it just comes with a lifestyle. There are no automated biweekly paychecks, there is no certainty of repeat clients tell there's not even a predictable schedule that's going to be laid out for you. You may get no calls for two months. And then you may get followed up with 10 and a week. real-world example. charting out a monthly budget without knowing what your monthly income is going to be. the anxiety of doing that can feel overwhelming to a lot of people, myself included. And I'm not suggesting that you have to be happy with this level of uncertainty to become a successful freelancer, I just want you to consider the mental health aspects of such a move. If you're pushing all your chips, and this is bold. There is risk involved. You have skin in the game now. I mean, if self-employment doesn't work out, you're moving back in with your folks. So when I say Are you okay with uncertainty, I'm really asking you, how much fortitude Do you have to see this through? Are you committed to making smart decisions as opposed to impulsive ones? Do you have the fortitude to avoid equipment upgrades, just so that you can pad your emergency fund, Lee Trevino for all of you millennials out there is one of the greatest golfers of all time. And one of his best quotes reminds me of the anxieties that you're going to face as a freelancer really resonates with me goes like this. You don't know what pressure is until you've played for $5 a hole with only $2 in your pocket. Folks, if you bet your livelihood on freelance income, there's just no way around it. You will have to develop thick skin, you will have to adapt to this level of uncertainty. And it's not easy. I get that studies show that times of uncertainty are actually met with more stress than knowing something bad is going to happen. That kind of blows my mind. But think about it. Would you be more stressed out wondering whether you're going to make it to your job on time versus knowing you're going to be late? I'm in camp A, I'd be more stressed out about wondering if I'm going to make it on time. Or how about this thought experiment. Would you have been as stressed out about COVID-19 impact If you were definitively told the exact amount of time it would last, and the day would end? Or would you take comfort in knowing how long you had to hunker down for how much to save up? How aggressively you had to pivot your career. When you know the results, you can prepare for that one thing. When you don't, you have to prepare for everything. So if you're starting to think about becoming your own boss about going off on your own, I only have one recommendation. And that's to start preparing for uncertain times. Now, while you have the job, grow your emergency fund, kill off as much debt as you possibly can start saving money while you can. Because once you move off on your own, you won't have the safety net of a full-time job. If you can set aside 20% 30% of your paychecks. Hell, if you're living at home and you have mom and dad taking care of your rent, you can set aside 50 or 60% of your paychecks set that aside, specifically for freelance expenses, freelancers experience dry spells, wedding photographers may make 90% of their income in half the year. So you're gonna want to minimize the stress, the anxiety, and certainly the economic strain in those lean months, by using the income from the heavy months, consider your full-time jobs now as your heavy months. you're preparing for winter because it is coming. The whole goal is to prepare for uncertain times. Those winning in 2020 may not have foreseen this exact scenario happening, nobody could. But chances are they were fiscally prepared to handle this economic downturn, they were mentally equipped to move on from job loss and hit the ground running with their next move. 

Alright, so moving on to question number two, will you be okay shooting just 10% of the time. Now, I'm not saying and guaranteeing that you're only going to be shooting 10% of the time, or designing or building or whatever your creative skill set is. Some freelancers really do shoot a lot. What I'm really asking you is hypothetically, would you be okay if the majority of your time is spent on business as opposed to shooting, because as a freelancer, you're not guaranteed to get assignments sent to your inbox all the time. It's great when it happens. I know I love it, but it can just as easily go ice cold. Take for example, this past year of 2020 I can't count how many sports photographers stopped getting assignments sent to their emails when COVID happened. To me this had to have woken everybody up, woken them up to the notion that this lifestyle, this full-time freelancing thing is not always for the passive, you might be successful with one big client giving you volume assignments in the short term. But if that dries up, you'll discover very quickly that freelancing isn't automatic, that it's not always easy. The reality is most of us have to work a much longer process, we have to see clients out, we have to pitch them a concept, figure out our pricing, negotiate things like usage rates, copyright terms. And then after that, we have to plan the shoot, execute the shoot, collect payment, deliver the images, and then continually market to that client, so that you're always on the radar. That's realistic freelancing. The point I want to drive home is that you're not just a creative entity I wish you were, the creative part might only be a small percentage of your actual duties. So think about this. You're not just a photographer, you're also sales, your marketing, your the legal department, accounting, r&d, customer service, the list goes on, you don't have anybody to pass the buck to. So I asked you How comfortable are you taking the time to learn things like intellectual property so that you can educate your clients on the appropriate usage? How comfortable are you negotiating terms on a contract or preparing an estimate or trying to collect on delinquent payments? This not only takes time to learn, it takes time to execute as well. So I recently saw this interview with Mahershala Ali, who is one of my favorite actors. And he won Oscars for moonlight in Green Book and he's absolutely brilliant. And it reminded me that most of us really don't see what goes on behind the curtain in our own creative field until we get into it. And he said, and I'm paraphrasing here, he said, You really only act between action and cut like 10% of the time. The rest is prepping, building the psychology, wardrobe, makeup, studying meetings, press, etc. The actual acting is such a minuscule part of the experience of being an actor. So to think about this question in another light, ask yourself if that 10% of your craft is so meaningful to you that you're willing to endure the other 90% that you don't want to deal with. 

Alright, so there's one last question that I think you should ask yourself, and I hope you don't skip this because I think it's very important. The question is, am I being pushed into freelancing, or my being pulled into freelancing? What do I mean by that? Well, I think it's an important distinction. One is by force, the other is by choice. Now the unfortunate reality is that we're seeing and have been seeing for a long time, a lot more push a lot more force. These aren't choices to go into the freelancing market. A lot of people are losing their jobs. They're seeing their markets contract, maybe their company's fundamental business has changed in their hiring process, and how they view employees and contractors. We've also been dealing with a global pandemic that has completely changed and altered the economic landscape. No, I hope I'm being sensitive to everybody in this position that has either lost a job or seeing their business fall, it's not a great position to be in, you don't have a whole lot of leverage. And it just flat out sucks. I know, I've been fired before. And so if you're in that position, and you have to get some side gigs, pick up some extra hustle, you do what you have to do. So my hope for everyone, whether it's realistic or not, is that you find yourself pulled to freelancing. Instead of being a movie you have to do, I want this to be a movie you must do. Think about all the things you have to do in your life. Generally speaking, I'm going to assume they're not met with a whole lot of enthusiasm. I have to do laundry, I have to go to work, I have to go to class, I have to get the car fixed. These are external obligations. 'Must' signifies a personal obligation, something that's just for you something that you're not governed to do, but something that pulls you to action because it means something. It's a calling to ensure it might just be a difference in words. But I do believe it can change your psyche, it can change your attitude towards this new situation. Choosing freelancing is often met with more enthusiasm, and excitement and fulfillment and peace of mind. being forced into it is typically met with anxiety, fear and shame. Now, it doesn't mean that if you're pushed into freelancing, that you're going to hate your life. If that happens to you, I encourage you to simply change your narrative. Don't tell yourself you have to do this. Tell yourself you must do this, and the quality of your freelancing experience can ultimately change. 

I hope these questions help you in your journey and I do apologize if you are seeking Surefire answers instead. I know that telling you what you need might give you a clearer direction. But I'm an advocate for self-discovery. I want you to ask yourself questions that only you can answer. This episode was a nudge to get you going. I can't tell you what to do when it comes to this type of move. And I've seen people jot out a full business plan with financial advisors and family members. And I've seen people jump in headfirst without any clue what to do next. I've seen both approaches succeed. And I've seen both approaches fail. Regardless of what you decide and how you get there. I hope you find your best creative life. And I hope it can support you along your journey.