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Too young to be taken seriously? Too old to be relevant? Where does adolescent inexperience meet youthful ambition? Where does late start meet experiential wisdom?

I think if you’re asking the question, you have what it takes. It definitely takes hard work, but you’re not too early and you’re not too late.

Are you living for 2 weeks out of the year or are you making the 52 worth living?

Show Notes

    Question: “Is it strange being 20 and a full time freelancer?”

  • 02:42 Sean: What do you think this person is feeling? Maybe in their circle, this is fairly uncommon. They feel weird, they feel like the odd one out.
  • 03:16 Ben: “Maybe. Or if things are going well, they may feel like this is strange. ‘Should I be able to do this so soon? Have I skipped something that I was supposed to do? Did I take a shortcut that I wasn’t supposed to take that’s going to cause issues down the road?’”
  • 03:43 Sean: That’s an interesting one. It can be weird doing your own thing at a young age and not having a lot of people around you that are doing the same thing. You feel different. You feel alienated. Everyone around you is talking about clocking in and out at a day job they’re pretty much all about the nightlife. You have a hard time relating to that. You’re focused on business, client acquisition, marketing, and it feels like you’re the odd one out.
  • 05:32 I think Adam in the chat room can relate. He says, “It’s a common feeling among entrepreneurs. They feel like they should ‘get experience’ first. I felt that way when I started freelancing full-time at 23.”
  • 05:47 But I didn’t want to just box this in and only talk about 20-year-olds because there are a lot of people at different ages and similarly, on the other end of the spectrum, you have people wondering if they’re too old to start doing this.
  • Why work for yourself?
  • 06:44 Upsides: You control everything. Downsides: You control everything.
  • 07:04 I want to talk around this idea for a minute by asking the question: When are we happy? This is just conjecture, but I think we’re happy when we get what we want, if you really simplify it down.
  • 07:22 Another question to open this up: What is success? Well successes another subjective thing. There’s not just this definition of happiness or definition of success—it differs from one person to another—but we know that success is not just money. Money can’t buy happiness. Sometimes we want things, and things can be bought with money, and we associate money with its ability to buy the things we want that make us happy, but sometimes the things we want can’t be bought with money.
  • What do we really want?

    We want freedom.

  • 08:02 We tend to associate things that give us freedom with “happiness” or with “success,” but really we want freedom. We want choice. Choice is freedom. It often doesn’t even matter what the outcome of the choice is. Sometimes we think the thing is what makes us happy, but it was really the freedom of being able to choose it.
  • 08:57 Freedom. When it comes to your job, freedom to do what you love to do vocationally. To wake up, do what you’re passionate about and somehow the bills are paid. Somehow money doesn’t even come into the picture.
  • 09:10 If you have that at your current job, there’s no reason to quit (Related: e086 Why You Should Quit Your Job). There’s no reason to go somewhere else or do your own thing. You don’t need to start your own business. If you work at a place that facilitates an environment like that where you feel fulfilled, hold onto that! It’s not a very common thing. It’s not wrong to not work for yourself. Working for yourself is not for everyone. It’s not a walk in the park a lot of the time.
  • 09:52 But for a lot of us, maybe we haven’t found that. Maybe we simply want the control setting our own hours and choosing who we work with and what projects we take on. Maybe we want a say in the matter of what clients we take on. Maybe we want a say in what products get built and what features to add and when they’re released and who they’re sold to and what problems they solve and how they’re marketed.
  • 10:20 You can’t do all of those things in someone else’s business! That’s where working for yourself fits the bill.
  • Working for yourself: is it easy? Heck no, it isn’t easy.

    It’s rewarding. I’ll take challenging and rewarding over easy any day.

  • Who Should Work for Themselves?
  • 11:30 You have two general groups:
    • 1. Younger person: “Is it strange being 20 and a full time freelancer?”
  • 11:57 No, I don’t think it is. I think if you’re asking this question, you probably have what it takes. Are all of your friends doing it? Maybe not. Maybe not now. Maybe they start later. I wouldn’t look to them to see if this is what you should be doing. If you feel like this is what you should be doing—if you’re asking the question—I say you probably have what it takes.
  • 12:21 Then on the other end:
    • 2. Not-as-young person: “Am I too old?”
  • 12:27 Here’s what I say:

    Stop thinking you’re too old to start something and be successful at it—you’re too old to do something that sucks for the rest of your life.

  • 12:34 Sean: Here’s how I define age: “Old” is over 100. We’ll call that “old.” Triple digits? Yeah, you know what, you’re old. You can own it. Be cool about it. Otherwise? You’re not old. Don’t worry about it. There’s “young” and there’s “younger.” You don’t need to put yourself in some other category just to discourage yourself.
  • 13:45 People tend to look at the things that make something harder to do rather than the positive or upsides of the current situation they’re in.
  • 13:55 If you’re younger, there are benefits to being young:
    • You have a lot of potential.
    • You have life ahead of you.
    • You have plenty of room to make mistakes.
  • 14:13 Ben: “You know, you can’t ignore the outside perception of a person who’s young vs. a person who is older and starting the same thing.”
  • 14:25 Sean: Well, right now I’m just listing the positive aspects.
  • 14:30 Ben: “Well, that’s what I’m saying: that is a positive aspect. There’s this perception because someone is young, it makes the fact that they’re doing this a little bit more interesting and intriguing.”
  • 14:45 Sean: I just realized what happened. When you said that, I immediately jumped to the opposite conclusion. I thought you were speaking to stigmas associated with being young: “This person’s young, I don’t know if I want to hire them,” or “This person’s young, I don’t know if they’re really serious about what they’re doing.” That just goes to show you that there’s two sides to this coin—on both ends of the spectrum.
  • 15:15 Some people see it as old and wise, and others see it as old and outdate, or old and irrelevant.
  • 15:33 Ben: “Yeah, you have a tendency to see the negative in the place where you are. If a younger and older person both put out quality work, I have this tendency to think that the younger person is displaying amazing talent for a person of his or her age, whereas you should just expect something of that level of quality from a person who is older. The older I get, that’s the thing that causes me more anxiety—this implied expectation of quality that comes with age.”
  • 16:34 Sean: Right, whichever end you tend to be on, you look to the negative. You look to your insecurities.
  • 16:46 When you’re young: “Did I take too many shortcuts? Should I even be doing my own thing? Should I have my own business? Should I be working for clients when I’m this young? Should I have gone through all of the normal hoops that everyone else did?”
  • 17:00 But really the other person sees the good on your end. They look to the younger people and think, “Man. Look at them. They’ve got their whole life ahead of them. They have all this potential. They can do things wrong and they can correct and they’ve got 20 years before they catch up to me!”
  • 17:31 Meanwhile, the young person says, “Look at this person! They’ve got 20 years on me. They don’t even have to work as hard as I do and people will take them seriously just because they have facial hair and I can’t grow a beard.”
  • 17:44 Ben: “No, you can’t.”
  • 17:46 Sean: Ben, you weren’t supposed to call out the fact that I was talking about myself.
  • 17:49 Ben: “Ohh… I’m sorry. You know, if it makes you feel any better though, Sean, I have difficulty growing a beard in some places. It just doesn’t connect.”
  • 17:58 Sean: It doesn’t. It doesn’t make me feel better.
  • 18:17 If you’re young, you have things going for you. But if you’re not as young, you have things going for you too!
    • You have years of experience.
    • You have perspective.
  • Focus on the Good
  • 18:49 No one is worrying about your insecurities. They’re not critiquing you, they’re looking at the good stuff. You need to look at the good stuff. If you’re young you have things going for you. If you’re not as young, you have things going for you. You have years of experience.
  • 19:06 Even if you’re not experienced in this thing that you’ve decided to pursue right now, you have some kind of experience even if it’s diversified. That’s life experience and it’s going to apply in one way or another to the things that you’re doing. You also have perspective. You’ve been there before. A lot of the things that this younger person is struggling with, you’re not struggling with anymore! But you forgot that you’re not struggling with it because you’re already past it. You’re struggling with what you’re struggling with now and if that’s all you ever focus on you’re going to feel like you’re perpetually in a terrible situation.
  • 19:51 There’s always something new, you’re always learning, it’s just a matter of what you’re focusing on.
  • 19:58 Does this mean just jump out into working for yourself without a foundation? Of course not. That’s what The Overlap Technique is for (Related: e102 Why It May Be the Wrong Time to Pursue Your Passion).
  • Let’s get real about responsibility
  • 20:24 The older you get, the more responsibility you tend to acquire.
    It’s like fridge magnets. Where the heck did those come from?
  • 20:57 You have to be real about your responsibilities. Take stock of those responsibilities:
    • What do you have to do?
    • What are your baseline responsibilities?
    • What are you not doing?
    • What are you saying no to?
    • How are you making time?
    • With the time you make, how are you dedicating it?
    • It has to be on the schedule.
    • Get your family on board.
    • They’ll keep you accountable.
    • No excuses.
  • 21:34 If you’re younger, you have so much freedom right now. You don’t even know how much freedom you have.
  • 21:41 Your tendency is going to be to fill this time. There are so many opportunities and things vying for your time right now. There are a lot of frivolous pursuits you can get wrapped up in. A lot of time-wasters.
  • Look at the people who are 10 years older than you who did the time-wasters you’re thinking about doing. Ask yourself: Do you want to be where they are?

  • Work Hard First – Then Enjoy it
  • 22:11 Find something you enjoy, and apply yourself. Work hard at it. Find something you love the act and the process of doing.
  • 22:27 This is a subtle difference, but it makes all the difference in the world. Everyone else says, “Well, of course you won’t like your job, but eventually you’ll get promotions and maybe after 10, 20, or even 30 years you’ll work your way up and have a lot of money and it’ll be worth it.”
  • 23:59 Worth it? Worth what? 30 years of your life? You just sank those years.
  • This isn’t some game. This is your life.

  • 24:13 I’m talking about working hard now at something you enjoy doing and putting in the effort up front.
  • Living for 2 Weeks Off
  • 24:25 I used to be envious. You’d see other people right out of high school or college going on trips, traveling the world, taking pictures of themselves in cool places.
  • 24:44 But when they come back, they’re starting at the beginning. They’re starting at square 1 and they have to build up. There’s absolutely nothing wrong with doing that, but people carry this mindset with them throughout life. They just “get by” at a day job that they hate because everyone says “Of course you don’t love your job. Nobody loves their job. Just work hard and you’ll eventually work your way up.” But that leads to Golden Handcuffs. Eventually, you’re so invested—you have so many decades of times sunk into this job that you don’t want to be at, you can’t even convince yourself to leave. Because you’re paid a decent amount now and you’ve invested so much, if you leave here, what do you have?
  • 25:41 Ben: “And they’re saying, ‘Now I’ve got several weeks of paid time off'”
  • 27:06 “When you go out into the workforce and get a regular job. they try to sell you on a week of paid time off. ‘After your second year, we’ll bump it up to 2 and a half weeks!’ There’s something that feels a little bit like instant gratification as opposed to building something.”
  • 29:29 Sean: Whether you’re working for someone else or working for yourself, both routes offer a similar benefit—just in vastly different quantities. In the day job, you go to work 50 weeks out of the year and you get 2 off. For those 2 weeks, you get to just be about life and doing whatever the heck you want and just enjoying yourself. You could make something, you could build something, you could do absolutely nothing, lay around, relax, go to the pool, go on trips, travel, climb mountains, hike, scuba dive—whatever you want to do in this life you can do that in those two weeks.
  • 30:17 There’s 50 weeks in the year. Imagine a group of 50, colorful children’s blocks, and then picture 2 blocks next to that group. That’s what you get each year.
  • 30:36 The other option is working for yourself. You may be putting in a lot of hard work for the first 5 years, but after that you have the potential to have those entire 52 blocks to do whatever you want and still have your bills covered. Now both of these situations extend throughout the rest of your life. Maybe you get retirement out of the other option if you work somewhere for 30 years. But the quality of life and the lifestyle you’re able to maintain after retirement is also limited. In a lot of cases you may have to still do a little bit of work too.
  • 31:28 So which is worth it? You can start right now accumulating those 2 weeks per year that you get as a vacation, or you can start right now building something of your own. You can start building your own thing and working for yourself and eventually being able to do whatever you want while all of your bills are covered. Inevitably, if you started building something you enjoyed, even the stuff that you do when you’re not worrying about making bills will continue grow your business because you started with what you’re passionate about. A benefit snowball.

The perfect age to work for yourself is 10 years ago.

The second best time is right now.