Is Now the Time to Start Freelancing?

In the inaugural episode of 'Second Act Freelance,' host Judson Voss delves into the reasons why experienced professionals might consider freelancing either as a side hustle or a full-time endeavor. He discusses the economic and personal factors that make the current moment ripe for starting a freelancing career, including economic expansions and contractions, the impact of COVID-19 on remote work, and personal factors like risk diversification and control over one's work-life. Voss emphasizes the shift in corporate mentality towards hiring freelancers for flexibility and cost reduction, and the increased feasibility of freelancing from anywhere due to remote work infrastructure. He also introduces resources available on his website, including an eBook designed to help individuals evaluate if freelancing is right for them, and encourages viewers to subscribe for future episodes that will explore freelancing in more depth.

00:00 Welcome to Second Act Freelance!

01:02 Why Now is the Perfect Time to Start Freelancing

01:34 Navigating the Big T Time: Economy and Infrastructure

05:31 Embracing the Little t Time: Personal Reasons to Freelance

07:00 Taking the Next Steps Towards Freelancing

08:25 Closing Thoughts and Call to Action

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Transcript

Welcome to second act freelance. My name is Judson Voss. And, uh, last week on the podcast, we discussed a little bit about why now is the right time to become a freelancer potentially. So the next logical question that goes along with that is, is it the right time for me to be a freelancer and number one and number two is freelancing.

Even for me, um, if you've been a professional working in the work environment for a long time, in a, in a corporate job, you've probably gotten pretty used to how things work. If you're successful, you've learned to navigate the situation. But, uh, when it comes to being a freelancer, you can still take those same skills, the hard skills, the technical skills that you've picked up over the years and use those.

But, um, you're also going to have to. Think about, do I have, or do I want to learn some other skills that go along with essentially being a business owner? So today I'm going to break down a few different things, and then in future episodes, we're going to go into each of these more in depth, but today I just want to go over sort of the cursory picture of it.

Don't know that that's a word. I think it is, but somebody will look it up and send me an email. If it's a word, actually, nobody's going to send anything. If it isn't, then I will get hate mail. It's okay. That at least something, something is good. Any reaction is good enough.  Um, so, uh, as far as other things you can do.

Uh, sort of along this path, I do have an ebook called, am I ready to be a freelancer? Um, feel free to go over to the website, second act freelance and download that. And you can walk through a little bit more details. A few exercises. There's a couple of little tools in there to be able to use to discern is now the right time for me to, to freelance.

And is it the kind of thing I want to do? The other thing you can do, of course, is like, and subscribe on YouTube or favorite the podcast and, uh, On iTunes or wherever you get your audio podcast, and then you can hear more about this as we have upcoming episodes,  um, without boring you about myself. I've been freelancing for, I think it's about 7, 8 years, something like that.

Obviously, I've been in the job market a little bit longer than that. So working at corporate jobs, have my own business, a few different things. The book, I go into a little bit more detail, so I'm not going to spend a lot of time today on that. Um, but before we. New sort of dive into, am I ready to be a freelancer?

I always like to start with the question, not of how or what, but why? Um, and I think in anything in life, if you have a strong enough, why you're going to figure out the how and what I know it sounds cliche, I think it actually is a cliche, but, um, the, it, it is also, you 100 percent true. So I just want to throw this out there is something to think about as far as the big question for the day.

Um,  if you're in, like I said, a lot of folks that are watching and listening are  second act a little bit later in their career, and so maybe you're 45, 50, maybe a little bit beyond that. But the question is if you're, let's say you're 50 and you want to retire when you're 65, that. Using my calculator means that you have about 15 years left in sort of your professional work life.

You may not want to retire, but I'm using this as numbers. Um, and so my question is this,  if you were to.  Take the fact you have 15 years left  and you said to yourself, you know what, uh, the first 30 years, like if we have 15 left, first 30, that's a round number as far as where we're at  over the next 15 years. 

Do I want to do one of, I want to do one of two things. I want to double down, take everything I've learned in the first 30 years and use the next 15 years to quadruple the impact that I've made  in the first 30 years.  And then the other thing I can do, or I can ask myself this question, is this what I want to do is take the next 15 years and keep it status quo.

And they're not saying there's anything wrong with that, but  you need to ask yourself the question. And so. You know, over the next 15 years, what does that look like for you and your professional life? Is it continuing on? Is it moving up the corporate ladder further though? You may be at the top of the corporate ladder and near it right now.

I mean, if you're a,  if you're a CMO and marketing and you have no interest in being a CEO, the only other move Corporately isn't another CMO role, I guess. Um, well, or you can be asking yourself, how can I take the next 15 years, build a business, build a brand for myself and take what I've learned in the first 30 years and turn it into something else  again, even though I'm setting it up like that matters that I'm picking a over be  more importantly than what I think is, is what you really want to do because intentionality is what's going to make a difference, especially.

If you want to be a freelancer, because sort of meandering around and freelancing is not going to do it for you. You need to have a plan and you need to have your why. So ask yourself that question. What is my plan for the next 15 years? And what is the impact I want to make over the next 15 years?

Financially, in the market, with my family, whatever that is. And I think that's going to help you start to set yourself up for the why of freelancing and what you want to do.  So if I had a sponsor, this is where we dropped the sponsor in there, but I don't, so I'm just doing this for free. Um, if you want to sponsor us, we're more than happy to have a conversation about that, but otherwise we're just going to uncomfortably  move on to the next section. 

Um, so today, as I mentioned, I want to talk about, am I ready to be a freelancer and sort of go through at a high level, some of those things that you want to think about.  freelance. com. I've got the ebook there. If you get tired of listening to me, drone on and on, feel free to go over there and read that instead at your leisure.

Um, it's going to go into more depth than what we're going to talk about today, but in future episodes, we will go into more depth into each of these. And I am really, really, really trying to focus just on The question, am I ready to be a freelancer and not the question of how do I freelance? What do I do next with each of these things?

We'll get there, but for now, it's just about, you know, looking at these things, what it takes to be a freelancer and to go into it with your eyes open. Um, and really most importantly,  if you've sold yourself on this and you do want to be a freelancer and to create a freelance business.  The question is, is it now, and if it's not now, what are the gaps that I have that I need to fill in before I get there?

Or maybe it's part time now. What are the gaps I need to fill in to get to full time? And those are really important things to think about. Again, like I said, intentionality is the key. And so going through each of these and thinking from that perspective is really helpful.  So number one is time.  I would love to say, hang a shingle out tomorrow, maybe.

And all of a sudden you are. Rocking and rolling and you have people coming in and your biggest problem is how do I invoice all this, uh, billable hours and time and contracts and everything like that,  most likely that won't be how it is from day one. If it is for you, great, great for you. That's awesome. 

But for, for most of us, it doesn't start that way. The, the, it starts by building something and figuring out what each of the steps are and. Answer the question. Do I have the time to commit right now to get into it? The reason I say, do I have the time to commit is I think if you really want to build a freelance business, no matter where you're at in your career, no matter what's going on,  if you're not honest with yourself,  figuring out the amount of time it's going to take you to do it and what you want to do, uh, to commit as far as time into that, you're going to find yourself meandering and you're going to find yourself not doing it.

And you're going to come back here three, four, five months from now and say, you know, this. This freelance thing didn't work out because, um, I didn't really get any traction or do anything for it. So first thing is think about, do I have the time? Do I have the time to learn what it takes to be a freelancer?

Do I have the time? We'll go into some of the other steps later to go through those steps. And, um, how long do I want to take and what kind of time commitment do I want to make daily, weekly, whatever that is to start to build or put the steps in place to build my freelance business.  I think being honest with yourself will get you a long way there.

I also think if you can  choose that time and you commit to that time, I'd be really surprised if you're not successful, if you do some of the other things that are needed.  The, the second thing I think about when it comes to freelancing is less, uh, measurable because time I can measure that to have the time it takes.

But the next question is, am I cut out for it? And I don't mean, are you mentally strong enough or, or, you know, are you, are you good enough at different things? But is it the kind of thing I want to do? Freelancing is not like a corporate job where you go in Monday through Friday, eight to five, assuming the economy doesn't tank and you don't mess something up really bad, then you still have a job.

And at the end of the week, the month, whatever that is,  you get a, uh, a direct deposit in your checking account. Freelancing is, is less, um, predictable. It may still be consistent, but it's less predictable and you may, but you do, you may have some ups and downs and income. You may have times when you think, you know what, um, I'm looking down two, three, four, five weeks from now.

I don't see where the next thing is going to come from. And I'm nervous about that.  Ask yourself the question. Is that something you thrive in? Uh, and if it isn't, is it something at least you can. Put up with, or number three, giving you three choices. Or is it something that you're willing to learn how to handle? 

Just be honest with yourself. If the thought of not knowing where your paycheck's coming from six weeks from now,  but having a feel for what the options are, what the possibilities are, but still not knowing for sure, if that knots up your, your stomach, then you need to take that into account and be honest with yourself. 

Is freelancing for me now, we'll talk about some different things later on. Fractional contract work, those types of things that will mitigate that. But I think knowing which of those and what your threshold is for unpredictability and change really will help you guide your way into the different places.

And maybe you say, you know what, right now this isn't me. Maybe it's something I want to do in the future and I want to work on it and I can do that. The other thing personality wise that I would seriously consider is self discipline. Um,  if, if you're the kind of person that needs a supervisor to plan out your schedule for you and tell you, you know, this needs to be done on this day and I need a deliverable here or even, um, You know, the deadline is here.

I'm going to check in on you every day on our, if we're there, let's take the deadline and chunk it down into daily pieces. Um, I'm not saying you don't work in an environment where you do that. I'm saying, do you need that to accomplish things? And if you do, then one of two things, one is you may not be cut out to be, to freelance and work on your own, or number two, you need to know that going in and have a plan to mitigate for it.

So do I need a project manager to work with me? Do I need some type of accountability? Whatever those things are, if it's not your strong suit today, having self discipline and motivation and keeping yourself on track, then you need to think about what do I need to do to make that happen? If I really do want to freelance, like I said, don't exclude yourself from freelancing because of it, but think about what you need to do to mitigate those pieces. 

The number three thing that I would think about it, if you're ready to freelance is your network and your connections. And I'm going to go into this a lot throughout this podcast. If I had to pick one thing that I honestly, truthfully, 100 percent believe  affects whether you will be successful in your freelance business, and maybe in a lot of businesses out there, if you start your own business  is, is your network and connection. 

Jeff Henderson has a awesome book about going out on your own. And one of the things he talks about in there, and he's a big proponent of networks also, is that, uh, what, you know, and I'm going to mess up this quote, I'll find it later and put it in the show notes, but what, what you, what, you know,  affects your income much less than who, you know. 

And when it comes to freelancing, there is nothing any more true than that, that who, you know, and I'm going to throw a caveat in there, who you can get to know  is more important than what, you know, now,  If you know way more than everybody else, you may get paid a little bit more per hour or whatever that is.

And maybe you get better, bigger jobs. That could be true. But as far as the overall income and having work, who you know is much more important.  And when you think about it, are you ready to be a freelancer? Um, I'm not saying you need to have a big network today. I'm not saying you need to have a network or connections today.

What I would say is you need to think about the fact that this is ultimately important  and, uh, since it is ultimately important,  am I willing to put in the work to build that network and those connections  and in the, in the ebook, I mentioned, um, Am I ready to be a freelancer to talk about my, myself and my personal story.

So just to give you a feel, and I think just rough numbers,  I maybe had 10 people in my network that I considered when I, when I started out, um, three of them.  We're interested in giving me work at the time to varying degrees, a couple of just a little bit here, there, uh, four of them  were interested in helping me find people.

They could give me work as in they had some folks in mind that they knew of, they didn't need any. Work right now, but they already had some people that they thought of. They're like, needed my help with what I do. And then I had three other people that were like, you know what? I haven't heard from, I called all these people that I've heard from you.

I'd love to go get coffee with you.  And out of those 10 people that, that gave me enough to, to  believe it or not, get a week's worth of work every week, um, going on seven years now,  I'm not still working with Just the same people, some are, but not just the same people, but those three people that were willing to give me work at the time, just to give you a feel, um, where I think at the time we're going to give me 15, 20 hours worth of work, which was a pretty considerable amount, especially since,  uh, 40 hours of billable work in a week would be a lot for me.

So 20 would be a lot more than half. And I had those people up front. So.  Was I ready to go full time? I wasn't, but did it give me the confidence that I could potentially if I wanted to? Yes. And so that's where I want you to start with where you at again in the book. There's some exercises, but just one quick tip, just start writing down all of the people that you know that either may.

Provide work for you or may know people that can provide work for you. Or maybe you don't know that they can do either, but you'd like to get to know them in the ebook. I go through, I think it's a different places. You can find these people. Um, and you can go through those lists and write down the people, you know, in those, those eight different areas, but I will say out of anything in the podcast today, if you choose to do anything that I say.

Do this and I mean, worst case scenario, you don't want to be a freelancer. You have all these other connections you've now listed out. If tomorrow you decide you're tired of your job or you have to leave your job, um, you've got a nice list of people to start on. So day two. After you take a day off of deciding what to do next with your life, you've got a list already there.

So that one is a pretty low risk, spend 30 minutes, and you're going to set yourself up for success, regardless of you decide you want to freelance or not. So that's, that's my. Tip there, um,  also would say, don't make a mentalist right now. Whether it's on a piece of paper, a spreadsheet. I love notion, man. I wish notion would pay me money.

Cause I would do a bunch of notion videos and I just love it. But spreadsheet, you know, Google sheets, piece of paper, notes, whatever that is actually right. All of those people down and you'll get bonus points if you put the contact info in there too, but don't go and look for it right away. Then they're like Bob Jones, and then I'm going to spend 30 minutes finding Bob's email address and phone number.

Strike Bob Jones down when you get time later, if you don't have his info, go get it, just make the list now, make it hard, write it down.  Um, and so I should have done that as the last one because sort of anticlimactic and the one nobody wants to talk about. And that is your financial situation.  Your financial situation affects whether you are ready to be a freelancer, sort of in two different ways.

One is to what degree are you ready to freelance full time now? Now I'm not giving career advice. I'm just giving advice on things I've learned as a freelancer. But if razor's edge financially,  for me. I don't think it would be prudent just to make a leap and say, I'm quitting my job tomorrow and go start trying to find work.

I don't have any right now, but this is what I want to do. Maybe that's okay for you. But to me, that's just not the route I'd want to start on. Um, having that in mind, then the next question is  with the finances I have today, to what degree and when can I become a full freelance, uh, business  Uh, I, I like writing things down.

I like having a plan. I like making it concrete. I like being able to say, once I get to X, y, and ZI am fully in 100%. Well, I am mostly and partially confident  , that this is the, the best thing to do, and now the, the very least financially, it feels like I'm in a pretty good place.  I'm making up numbers. If I've got a year's worth of spendable income that I don't really need, and I'm ready to do this thing, then maybe it's the time to do it.

But you, you need to pick that number for yourself and do it for two reasons. One, one is I think it's wise to have a decision process in mind. And number two,  I joked about, you know, being a hundred percent confident, no matter how prepared you are, you're going to be nervous. And you want to be in a place where  everything you can do, you've done to feel good about pulling the trigger.

But the other thing too, is in, when it comes to your financial situation, if you feel good and you feel comfortable with it,  then it's one less thing to worry about.  You're always going to be worried about, do I have enough work? Where do I get work from until the point in time? And I promise it comes,  I've got too much work.

How do I start saying no, but that'll always be there. And to throw on top of it, where am I going to get my next meal from? And where am I going to get my next project from? Not a great situation to be in. If you're in a situation where you're like, I'm really pretty darn comfortable financially. This project came along, doesn't feel good to me.

I'd rather wait a couple of weeks to get something that I like a lot better. That might be there a lot longer. That will, uh, be easier on me. Stress wise, that's a better place to be. And so that's why I think finance as well, we don't want to talk about it. Uh, I think it's a really important thing.  And if you're not there today, just think about this.

If I put this in the ebook too, but you throw any numbers you want in there, if you,  If you have five hours of work as a side hustle type of thing every week, and you reach out to one of those people on your network and they're like, you know, I got like five hours worth of work a week. I could really use some help on give you a hundred bucks an hour to do it.

500 bucks a week, 2, 000 a month. And there's extra five hours. They're not impeding on your. Your your job. So it's, it's fine. You can do it. They're like, Hey, I don't care when you do it. It's not involved with meeting with anybody or anything. Just, just do the five hours, get the work done. This is gonna be a huge help to me.

And, and I'll, I'll give you 500 bucks for, for those five hours.  Um. In a month, you've got 2, 000 very worst case scenario. You just got yourself a vacation. You just paid for your next vacation, depending on what you do on vacation. That's a vacation for me and, and my, my two kids and my wife. Um, but you do that for six months, you got 12, 000 and maybe it's 12, 000.

You are now in that place where you, we were talking about, you feel very comfortable about considering going full time and the added bonus. Uh, you've just spent the last six months learning what it is to be a freelancer. So when you do go full time, all those little issues, those little things you had to learn along the way, instead of them being amplified to full time, you, you know, know how to handle them already.

And you're in a good place there.  So those, those are my, my four things that I would recommend starting with next time. We're going to go into two other things, um, which is to SWOT analysis, SWOT analysis is analysis  and now I don't know we're going to, we're going to do two exercises where we're looking at strengths, weaknesses, opportunities, and threats as another way to consider where you're at, how you position yourself.

As a freelancer in the business. And I think, so that's going to help you also with, am I ready? Where am I at? And then number two,  who am I in this huge pool of people that may be looking to do freelance work and where do I fit in best? So once you're ready, you're optimizing, uh, what kind of work you're doing, what the industry is, how you fit in those types of things.

So that would be next time. Um, As I mentioned before, too, you can head over to second act, freelance. com, download the ebook. Am I ready to be a freelancer? Also watch past episodes, read blog posts. It's just a wonderful place to be. Not really just a website. Um, but you can check it out there. You can also sign up for the newsletter and I will send out.

Weekly or occasionally when I get to it, I'm committing pretty strong there to, uh, put out some other information, some tools and tips and things like that, that we just don't fit into doing on the podcast. I will put that out there, um, on the website, second act freelance. com. If you're listening to this on a podcast directory, make sure you go over to YouTube and search for second act freelance, and you can watch the video though, man, I look a lot better on audio.

So you might want to just. Stick with that. And if you're on the video, head on over to one of your podcast directories or to second act freelance. com there's links there and you can get the podcast. If you want to listen, uh, while you're heading to work, doing your workout, whatever that is, and you don't want to have the, uh, have to have YouTube open on your phone all the time while you're doing that.

So anyway, uh, just encouraging parting shot. I think anybody can freelance. The question is, do they want to, and are you ready to, so going through these steps, thinking through that, I believe honestly will give you the confidence you need to one answer the question. Am I ready? And number two, if you're not ready, build a path to know what you need to do personally to get to that next step.