Becoming Better At Being Your Own Boss

becoming better at being your own boss
One of the most challenging aspects of freelancing, or starting a business venture on your own, is that you have to effectively fill two roles, the role of a boss, and the role of a worker.

If you’ve ever tried going out on your own, you know that it can be hard to strike a good balance between the two.

It can be particularly easy to be stuck in the “creative boss” mode, the “visionary” mode, if you will. Idea evaluation time will leak over into your worker time, and all of a sudden no work is getting done at all. Then when you finally get to working, it can be easy to tunnel-vision and end up going too far down a path that is doomed to fail.

Successfully navigating this tightrope-walk can tremendously increase your productivity.

Here are some of my own, and some borrowed, ideas on how you can become better at being your own boss:

Delegate Effectively To Your Worker Self

As simultaneously the boss and the worker, you have to find a way to delegate work to yourself in a way that it gets done effectively.

One way to do this, is monitoring how energetic you feel throughout the day for a week(or longer), and delegate the most draining work to the periods where you have the most energy. Another option is to experiment with the schedule itself.

I found that even though I’m not a morning person by any means, starting with focused work relatively early in the morning motivates me to put in a significantly larger amount of work than if I start later in the day. (Although the feeling of a head-start of waking up early can help, it’s really been about working about an hour after I wake up.)

Maybe it’s because it gives me a feeling of momentum, or maybe it’s because it gives me a semblance of a routine to rally around, where before I was all over the place.

(Seeing as studies suggest that the more groggy you are, the more creative you are, or how beer increases creativity(presumably for the same reason) it’s safe to put creative time at a point of the day where you don’t have a lot of energy.

Be Creative(But Only When It’s Useful)

After I started dismissing ‘creative thought’ unrelated to projects I’m working on as soon as it comes up, I’ve found it much easier to simply get the work done.

Also, in separating the idea creation part of writing for writing itself, I successfully eliminated one of the greatest barriers to getting my writing done.

The separation of planning mode and working mode is an idea I borrowed(stole) from Chase Reeves. His course on productivity on Fizzle is a must-see.

Show Compassion (But Not Lenience)

Compassion to me is an often underestimated quality when it comes to leadership. It is something that helps humanize the leader, and make him/her more inspiring.

And when you’re your own boss, it’s more important than ever, but for a different reason. Hopefully you don’t need to humanize yourself, to yourself. But when you’re first starting out, it can be easy to beat yourself up over something. And once you do it one time, it’s even easier to do it a second time. The third time easier again, until it becomes indistinguishable from an instinctive reaction to screw-ups.

Show some compassion for yourself. Don’t beat yourself up over failure.

The one thing that helped completely transform introspection for me, was looking at my actions as simply actions, and renouncing the “personal responsibility” that’s easy to put upon yourself after failing. If you look only at your actions, and inward insofar only as to see what has caused them, you will not imagine ‘character flaws’ in place where there are none. You will escape the regret and shame. You will end up looking forward, instead of backward.

Give Yourself More Time Off

Not only does research suggest that working over 40 hours per weeks makes you less productive, it is also (quite obviously) bad for your health, and even (not so obviously) your bottom line. Some research even suggests you should only work 25 hours a week (so maybe being a little short on the client-side isn’t too bad after all!)

If you’re already familiar with Parkinson’s Law, the idea that that work expands itself to meet the time available, you will probably distinctly remember examples from your own life where you felt the heavy truth of this sentence. If your workday goals are time-based, and are met as long as you are sitting in front of the computer with the intention of working for X hours per week, consider that the idea of the stereotypical wannabe writer that sits in front of his laptop at Starbucks all day can make the same claim.

Pareto’s principle also comes to mind, which states that 20% of what you do, accounts for 80% of the results. Give yourself more time off, and spend more time on what actually matters. When you give yourself less time to work, you might find that you intuitively tend to focus on higher leverage activities, rather than spending hours on twitter following and unfollowing people. (It’s also easier to test reliably what gives the most results when you only have the time to focus on one thing at a time.)

Think Less Do More

Chase Reeves, and Corbett Barr (of Fizzle), two people who have been there and done that, recommends that you spend a tiny amount of time thinking, and all the rest of the time simply doing. After all, it only takes a few minutes to think up entire months of work for yourself. (Paraphrasing something they said.)

Not only that, like I’ve mentioned before, thinking more doesn’t even lead to better decisions. Statistically speaking(according to research), thinking more will lead to worse decisions. (In fact, it might be better to not think it over AT ALL!)

So yeah. Straight forward advice here. Think less, do more.

Set Deadlines The Right Way (For You)

There is a duality to deadlines, as there is with anything. An impending deadline that seems challenging, but manageable, can push you to new heights of productivity, and speed up a project.

When you’re starting out, it can be hard to take your own deadlines seriously. And while becoming someone who takes your own deadlines seriously should be a priority, it’s more the case of building that habit than a “change in mindset”, which makes it more of a long term project.

Thankfully there’s another way. A quick fix. One that actually works. At least for me.

Growing up, I always felt that I needed the pressure of an imminent external deadline to get me moving. The moment I started to doubt whether or not I could make it in time, was the moment I sprung into action. I had kind of dismissed this notion until recently I read that Ryan Holiday finds that external deadlines help him considerably increase his creative output. And these last few weeks, after getting an external deadline in place where I could create my own schedule, I surprised myself by rallying to the cause and finishing a rough first draft for a 30-40 page project in less than a week. (More on that later.)

The improvement in productivity was something like 1000%, at the least.

While one of my long-term goals is to rely only on habits for productivity, giving myself free rein to work on a project. Parkinson’s Law (sorry to mention it again) has proved itself to be true for me, time and time again. So for now, I’ll be relying on external deadlines to get my ass moving.

Be Optimistic But Anticipate The Worst

The fact about freelancing, or starting a business, is that it doesn’t take too much for things to go wrong. The vast majority of new businesses wind up failing, and if all the horror stories out there are any indication, freelancing isn’t smooth sailing either.

So you need to be comfortable with anticipating bad things, and coming up with possible solutions, while also being optimistic enough to keep going when things get tough. (Or as Vincent would put it, an optimistic realist.)

One possible solution is to anticipate the worst and think of countermeasures when you’re feeling doubt, and focus only on getting things done when you’re feeling normal, uplifted or even inspired.

This has worked for me when I make a conscious decision to discard the doubt once I’ve thought of a solution to/the positive of whatever is causing the doubt.

Tim Ferris has some interesting thoughts on leveraging different states of mind in your entrepreneurial journey. 

Whatever you are when you start out as a freelancer or entrepreneur, you are going to need a fair does of optimism(or a lack of alternatives, perceived or otherwise) to keep you going when things don’t go your way.

Inspire By Example

To some people it might seem weird that I include “inspire by example” when I’m talking about being your own boss. But if you’ve been in the trenches, you know what I’m talking about. If you were productive the day yesterday, it’s a little easier to be productive today. If you were productive all of last week, it’s quite a lot easier. If you were exceedingly productive the last three months, well it’s almost hard not to knock it out of the park today too.

The terrible thing is that once you let up once, it can be a terrible uphill battle to get back. Especially if you give in to the urge to feel guilty about it and blame yourself. At this point it’s important to remember the step about compassion, (if you find it hard to give to yourself, you can outsource this role to a good, understanding friend. Talking about something I feel immensely guilty about, only to hear “I know exactly what you’re talking about.” Or “I do that all the time” has instantly lifted a heavy weight off my shoulders more than once.)

Take Steps Towards Becoming Healthier And Happier Every Day

At first I was going to say “make health and happiness a priority”, but it’s all too easy to claim that you’re “prioritizing something”, while really there is little, or nothing at all being done.

The first step is to give yourself more time off, but it won’t make that big of a difference if you spend the free time you give yourself in all in front of the computer as well. (At the very least not for your health.)

Gradually change your diet to be healthier. Exchange rice with browm rice. Potatoes with sweet potatoes, or beans. Sausages and processed meat with real meat or fish.

Start taking regular breaks during your working sessions, and minimize sitting where possible. You could for example brainstorm while standing, or walking, and dictate, or type (if you don’t like the awesome dictate feature, or it doesn’t like you) some notes into Evernote.

Know Humility

When something goes very right, instead of patting yourself on the back and concluding that you’ve “finally made it”, take some time to analyze exactly what lead you to your success. (Focus on actions and circumstances, not ‘imagined traits’.)

This exercise in humility can help you revolutionize the way you find clients/customers, or how do you negotiate the price of a project, etc.

Concluding success too early can lead to stagnation, decline, or even failure. Whereas staying humble can only lead to more progress, and success along with it.

One Thing At A Time

It can be tempting to try to tackle multiple areas at once. This is difficult for the master, and nigh impossible for the beginner. I find it liberating to focus on only one thing at a time, and it shows up in my productivity levels too.

Becoming better at being your own boss will not only help you as a freelancer or entrepreneur, it will ‘trickle down’ into other areas of your life too.

Ultimately, nothing will happen if you don’t do the work, but by becoming a better boss, you remove a large barrier to action, and make it easier to excel where so many fail.

(Also there’s something much more rewarding about play when you’re confident that you’re on the right path.)

Pictury by Thomas Geiregger (Disclaimer: I was not paid by Hugo Boss to write this article.)

6 Responses

  1. Ludvig Sunström June 27, 2014 / 3:19 pm

    Hey Ragnar!

    Haha, there is no way I’m buying that you’re supposed to work only 25 hours a week.

    5 hours of work per day… What are you supposed to do the rest of the day?

    • Ragnar Miljeteig June 30, 2014 / 3:51 pm

      I think the research is on the standard soul-smothering, life-draining, any-5-year-old-can-do variety desk job. Maybe the 5 hours forces you to focus solely on doing more stuff that actually matters, and spend less time dilly dallying. It sounds a little far-fetched, but it’s worth a try. (I guess reading/researching could be done outside of “work hours”, as well as networking, working out and that kind of stuff?)

  2. Jacky June 28, 2014 / 11:32 am

    Being humble (especially if you are killing it in a particular area) is incredibly important. I always remember how Mike Tyson said in some interview, that if you are not humble, life will thrust humbleness upon you.

    • Ragnar Miljeteig June 30, 2014 / 3:52 pm

      Definitely. Very well put. I will remember that one.

  3. Micah July 1, 2014 / 8:41 am

    I think the self compassion thing is a really good point. Along with becoming more strategic and deliberate about scheduling. I’m still getting a handle on it but I’ve been finding that structuring my time and devoting specified intervals to specific work is hugely effective. I do think keeping the working hours down is important too but it’s very difficult to do when you’re your own boss. I find I rarely truly switch off from projects I’m working on. Even when I’m not working I’m still working – I’m thinking, researching and reading around a topic or work item I have pending. I do way more hours now than I ever did working a regular job. I just don’t notice it as much, until my wife points out I’ve been writing since 8am and am still writing at 10pm that is.

    • Ragnar Miljeteig July 1, 2014 / 10:58 am

      Very relevant. One of the problems with working for yourself is that much the actual work is ambiguous. It can be easy to categorize it as “not really work”. But of course if you had a job, you would do your hours and that’s it. I tend to clock mostly my “writing hours” as my research has a tendency to become unfocused. (Maybe I should try offline research for a change, haha.)

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