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You Get By With A Little Help From Yourself

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Fellow Riskologist,

When someone with a traditional job asks what it’s like to be self-employed, my favorite answer is: “It’s totally amazing, but my boss is an asshole.”

The answer’s a joke, of course, but anyone who’s self-employed knows there’s a bit of truth to it.

Going to work, most people are accustomed to showing up and having a list of things they need to do handed to them. Someone else has already decided what needs to be done, how it needs to be done, and when it needs to be done by. There’s little room for interpretation.

And while you’re living it you sometimes grow to despise it, breaking free presents its own set of challenges. You start down the path of self-employment and, suddenly, the system is gone. The only one who’s going to make any decisions is the same person who’s going to implement them—you!

You’re thrust into a world where everything is new and unfamiliar. Each day at work feels completely different from what you’re used to because you wake up and there’s no agenda.

  • You’re the one who decides what time work starts and ends.
  • You’re the one who chooses what to work on.
  • You’re the one who picks how to do the work that needs to be done.

If you don’t know how to make those decisions, there’s no one in the office next door to help sort it out for you. You’re the boss of yourself now. And that sounds cool, but it’s actually kind of hard.

So, you tend to go one of two ways. Either you:

  1. Become a total asshole to yourself, driving yourself to work harder and longer and give up on the idea of relaxing or doing anything non work-related because damn it, you’re going to make it! Or,
  2. You slack off, paralyzed by all the decisions to make. Nothing gets done and, eventually, the gig is up—back to a job where someone will tell you what to do again.

Some people slingshot back and forth between the two. That’s how I operated for years—one day waking up at 5AM and working until midnight without so much as looking out a window, the next sitting around not sure what to do and getting nothing done as a result. Either direction you go, you aren’t treating yourself right.

You don’t have to be self-employed to understand this predicament.

Almost anyone can relate. Perhaps you can remember a personal project you struggled with. Maybe you got so engulfed in it you tuned out other important parts of your life for too long. Or maybe you just never finished it because there was no one around to drive you to get it done.

Today, I’m far from perfect in this department. I still find myself working long hours from time to time and focusing on things that are unimportant. And, once in a while, it all just becomes too much, so I sit around doing nothing for days on end.

But I’ve reigned the problem in over time as I’ve learned how to better manage myself. Even if I struggle, I can pull out of it quickly.

The trick is learning to master your mindset and how you motivate yourself. I do it in a very odd way…

When I’m struggling and falling too far to one end of the spectrum, I remind myself what it’s like to work for a great boss. More than that, I try to picture another copy of myself sitting next to me, working away at something important, but occasionally checking in to see how I’m doing. I become that great boss.

It’s almost a type of astral projection where I picture myself leaving my body and looking back at myself through the eyes of someone else.

He can see when I’m working too hard and missing the bigger picture. He reminds me I’m running a marathon, not a sprint, and that if I always have my head down, I’ll run off course because I won’t see where I’m headed. He reminds me there’s more to life than finishing tons of projects and that there are people who want and deserve my attention.

And when I’m suffering from analysis paralysis and sitting idle, he knows I need to be reminded that no one knows all the answers ahead of time. He tells me what’s important is that I keep moving forward. The more actions you take, the better you’ll become at recognizing the right ones in the future. The faster and more accurate you’ll get.

When I take the time to have these strange, private moments with myself, they always get me re-aligned and working on the right things at the right speed.

Why does it work? Because I offload the responsibility and stress of decision-making to someone who knows what to do, albeit in a very unconventional way.

One universal truth we can all relate to is that it’s easy to solve everyone else’s problems but your own.

Haven’t you ever noticed when a friend is struggling to make a decision, you know exactly what they should do the second you hear the problem. You don’t blurt it out but, in the back of your mind, you think to yourself, “Oh, that’s an easy one. Just do XYZ.”

Yet, somehow, you still struggle with your own big decisions, and your friends have their own internal dialogue over how easy your problem is.

In this case, you simply become your own friend. In my case, I try to summon all the good qualities of great bosses I’ve had in the past and advise myself using their wisdom.

But to do it well, you have to get out of your own head for a minute. You have to look at yourself through the eyes and mind of someone you respect and knows how to drive you. Then, you give yourself their advice.

This works tremendously for me. When I’m struggling to make decisions or when I’m working too hard and avoiding them altogether, taking a step outside of my own mind for advice from “my boss” always puts me back on the right path.

It’s weird, I admit. But if you struggle with the same problem… try it.

Yours in risk-taking,
Founder, Riskology.co

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What smart people are saying about this...

  1. Katie says:

    Great advice; wonderful post! I too struggle with the same thing. I really like your very pragmatic suggestion of imagining yourself sitting next to yourself and offering advice, suggestions, and observations. I think I will try that next time and see how it works. Thanks!

    • Glad you enjoyed it, Katie. It’s kind of a fun way to remind yourself of the things you say you’re going to do when you’re in the moment and thinking about not doing them.

  2. Marsha McCullough says:

    As Katie said, Great advice. It also helped that your song “title” is still ringing. I look forward to reading more of your work.

  3. Tom says:

    Great article. I can identify with a lot of this. After working on my business on nights & weekends for the last 2 years, I was finally able to replace the income from my professional job this past August. I am now on month 3 of being liberated from my J.O.B..

    I’m finding that one of my biggest personal challenges with this transition is letting myself take a day off to do something fun, or even just chill out for a day. For a committed entrepreneur, there is definitely a lot of truth in that “my boss is an asshole” statement.

    I definitely deal with analysis paralysis sometimes, knowing that there is work that “could” be done, but also knowing that if I don’t get out and do some fun stuff then that defeats the whole reason why I chose this path in the first place. Personal freedom, right? Maybe I should fill out some vacation requests and then submit them to myself for approval. :)

    • Ha! I love that idea, Tom. Maybe have a friend/family member make it for you, so that it’s tied to a real vacation with a real person.

      And congrats on growing your business and quitting your job. That’s a huge accomplishment. Feel free to email me any time with your story. Would love to hear more.

  4. Sean says:

    You are right it does not just apply to entrepreneurs. I am a highly self motivated software developer. Right now I am contracting. I tend to push and push and push myself to no end. I do this because it is worth a lot of money to me. I know that if I “kill it” at the contract job my potential employer will pay me more when they hire me full time.

    This kind of effort doubled my income in less than three years.

    But sometimes you just have to take a break. I have found in my life the best place to be is in the middle somewhere. Somewhere between pushing hard and being lazy. It sounds like you have found that too.

  5. Derek Murphy says:

    Nice. I find myself working 16 hour days, doing a lot of stuff for free or client work. A smart person would tell me to focus on developing passive products (books, affiliate stuff)and being mare selfish with my time.

    • Hey Derek. For some people, you just have to hit the breaking point before you make the important changes. That’s how I was.

      The good news is: You already know what to do. Now it’s figuring out how to get yourself to do it. You have to create new habits to replace the old ones.

  6. Andre says:

    It is funny you mention being able to understand everyone else’s problems better than your own. Had a conversation about this exact same topic with a (real :D) friend recently. First time though I’ve seen using the ‘virtual’ friend approach to solve your own problems. Genius!

  7. Kathy Gabriel says:

    There’s a whole lot more than a bit of truth … lots of truth. The experiences of being an employee give impetus to being self-employed. I’m not there yet, but soon! Great motivation!

  8. Mary-Beth says:

    As always, an amazing article. I don’t know if you have read Stephen Pressfield’s “The War of Art.” He talks doing what you mention, even to the place of having a project update meeting with himself (he’s a writer), typing the minutes, and putting them in his inbox for review.

    • Hey Mary-Beth. I haven’t read it, but it’s been on my radar for a *long* time. Sounds like he uses similar approaches to me. I haven’t handed myself any meeting minutes yet, though. :)

  9. Annika S says:

    Hey Tyler,
    this is actually perfect – I struggle with many of the same issues. I go through phases of super-duper productivity and then followed by non-activity where I watch TV for 2 days straight. I think the non-activity allows me to recharge for those high-drive days, but at the same time I don’t feel like the constant up and down is exactly healthy, at least not at those heights and depths.
    Recently I’ve been automatically doing the “boss” thing, just by coincidence. When deciding on my next task, be it either turning on the TV or starting the next to-do list, I have a conversation with myself. I’ve been achieving a much better balance because of it, although I may try visualising myself sitting beside me, see if that makes it more effective!

  10. Jane Hallowell says:

    You guys have a wonderful concept of what life should be all about at such a young age. I didn’t “hit the wall” until my mid-50s. And now, ten years later…

    You remind me somewhat of the philosophy of the 60s, yet, with a practicality that makes total sense. I’m impressed with your generation.


    • Jane Hallowell says:

      oops…I meant to click the box for “notify me of followup comments via email,” so, now, I’m clicking said box.

  11. Erica says:

    “…I try to picture another copy of myself sitting next to me, working away at something important, but occasionally checking in to see how I’m doing. I become that great boss.”

    This is the most brilliant idea I’ve read about this year. Thank you!

Founded with love by Tyler Tervooren

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