The Solo Side-Hustle: Managing a Team of One

Managing a Team of One

Managing a Team of One

If you’re a solopreneur side-hustle owner, not only are you blessed with mobility, flexibility, and nimbleness, you’re also cursed with self-motivation. When you’re the chief, cook, and bottle-washer. If you’re not working there’s no money.

There’s a lot to be said about working in a team environment.

The work gets done by multiple players. If a team is designed well, the best person for each job is assigned the task. Meetings are few and practical. Team members check-in and report their findings to the group.

Everyone works towards the common goal of bringing the entire team to the top.

With great teams come great leaders. You can fill a library with leadership books. Leaders have been trying to hack leadership since there were people who needed them. Great companies are built by great leaders. However, this doesn’t mean you can’t be a great leader of one.

What if you own your hustle 100%?

How do you manage yourself? Not only to stay motivated to keep working when times get tough (and they will), but also to ensure you’re doing the right work at the right time, in the right order?

In a minute we’ll un-pack the way I operate my side-hustle. I own an international publishing business serving 84 different countries, and I perform 90% of the daily operations from my pocket.

If you’ve got a solo side-hustle, there’s no reason you can’t benefit from some solid self-management.

When everything’s your responsibility, you don’t want to let yourself run-around with your pants down. We all need work structure. We all need to check-in. We all need short and long-term goals, with which we can measure our daily progress.

Here’s how you can too.


Start with the End

If we don’t know where we’re going, we can’t arrive. When you start with the end, you’ve got a benchmark—a compass point on the map. Take a day, a a few, hours, or even a week to dig-deep and unpack what you want your business to look like in five years.

As Tony Robbins says, “We overestimate what we can do in one year and underestimate what we can do in five.”

  • How big do you want to grow your side hustle?
  • Who do you wish to serve?
  • Will your side-hustle replace your day job?
  • How much do you want to earn every month/year?
  • What does the business model look like?
  • Can you operate the business in a way that matches your personality?
  • What are the ‘big rocks’ you must hit to reach your five year goal?

Once you’ve got your five year, divide that plan into five smaller annual goals. Next, divide the first annual goal into quarterly goals. Take the quarter and divide it into monthly goals. Divide the month into our weekly goals.

Now we’ve got something to work with.

Note each phase of your goals in a bound notebook. You’ll refer to this document often, so it’s important to make this a notebook that will last through some serious handling. Don’t worry, you’ll constantly revise your series of goals as you work through your side-hustle.

For now, this is where we’ll start. By the end of the year, you’ll have more done than you ever thought possible… and just imagine what you’ll accomplish in five!


Divide Your Week

When you divide your weekly goals into daily goals, you’ll have your main, must-dos that you’ve got to accomplish before bed. Yes, the world will throw everything at you. Given the current world climate, you’ll have new curveballs daily.

Your daily goals won’t be your entire to-do list. These are your giant rocks.

We do our best to complete the giant rocks before bed, leaving very few (if any) for tomorrow. By the end of the week we should have all the weekly tasks done. This is how we get to the five year goal at the end.

But the week/daily goals aren’t the end of our story.

We’re here to manage a team of one. That’s you. You’ve got all kinds of normal, human stuff going on. We like to procrastinate the tasks we don’t want to do. We love to chase shiny objects. Some days, if we managed ourselves, we’d be the first one to fire ourselves.

So, how do we keep moving, even when we’re being regular people? Simple, we have a Monday meeting.


The Monday Meeting

I got this idea from Steven Pressfield (author of the famous book The War of Art). He runs his own show. He’s been a writer for decades, treats writing as a blue-collar vocation, and understands the power of showing-up daily.

Pressfield has a Monday meeting with himself every week.

There’s a simple agenda. He takes notes. And most-importantly, he holds himself accountable to the wins and losses of the prior week.

We take the monthly goal, look at our weekly goals, and take note whether or not we’re ahead, behind, or at plan. I realize how crazy this sounds, but it works. I’ve been goal-setting for years, but I don’t refer-back to the plan often-enough.

Recently, I re-read The War of Art for the 10th time (I get something new with every read), and the Monday meeting concept finally stuck. I now have a Monday meeting with myself every week.

The process doesn’t take long. You’ve got all your metrics laid-out in advance. All you have to do is refer to your monthly and quarterly goals, look at where you are this week, and take some quick notes if you’re on-track or behind.

Note: there is no judgement during these meetings.

This is a productivity and motivational tool only. You are not allowed to pass judgement on yourself. “I missed the deadline because I was lazy this week.” No way! Instead you write what you did and what you should’ve done. That’s it.


Constantly Re-Adjust

Every Monday we’ll re-adjust our goals. If we’re close, maybe we’re right on target. If our monthly goal was too lofty for our marketplace, we work our way backward and re-edit the five year goal to meet the current situation.

This doesn’t mean you shouldn’t push yourself. Nor that you should let yourself off the hook when you totally slacked all last week.

But, when we start the five-year process, sometimes we 10X or 100X our goals to a place that we soon learn is unattainable in our customer base. On the flipside, maybe you crushed your goals and you’ve set them to low. The process works both up and down.

Now you know exactly what to do every day if you want to earn the brass ring at the end.

When you divide your giant aspirations into daily bites, the process becomes more do-able. When you have a Monday meeting with yourself, you have a clear, weekly picture of your progress (and a way to quickly adjust, should you need to scale things back).


Even Solopreneurs Need Managing

When you own your side-hustle, everything is your fault—the good, bad, and ugly.

Not only is this model very rewarding, it can also be stressful if your business isn’t where you’d like it to be. If you don’t implement a system to keep yourself on track, it’s easy to skip working today and meet your friends for coffee. Without self-accountability, it’s easy to chase a new idea, putting your current plan on-hold.

When you know you’ve got a one-on-one with the boss Monday, how do you feel?

You do your best to come prepared, right? If you’ve got a meeting in your day job, you probably start thinking about it Friday. If you’re smart, you thought about it all week. Some people wait until the meeting starts to recount what they’ve done all week.

Well, the meeting is now with yourself. You can be a good employee or a crappy employee.

You’ve got the toughest boss in the world—a real tyrant. If you don’t hit your goals the first week, you’ll probably come down hard on yourself. I did. But I tried to refrain from all judgement when I took notes.

The next Monday meeting will go smoother.

As you track your Monday meetings you’ll see your progress in real-time. Not only do the meetings help you track your goals, but they’re also motivating.

Add your Monday meeting to your calendar. Block it off in your calendar. Don’t miss your Monday meeting for anything. This might be the most-important meeting you have all week.


Never Stop Referring to Your Old Notes

Every Monday look back at your previous week. Take a quick glance at your monthly and quarterly goals. Flip to your five-year goals and see where you’re heading.

This constant referral process is the reason why I suggest a solid notebook.

Keep all your goals and Monday meetings in one place. I use a modified version of a bullet journal. This way I can carry-around a single notebook with my daily tasks, Monday meetings, and all the landmark goals down the line.

By constantly managing my daily workflow, I can divide these huge, lofty goals I have for the five-year version of me, and divide them down to manageable chunks.

The daily work becomes more-enjoyable, even when times are tough. I can see my progress in real-time. I’ve got the map. I know where I’m headed. All I have to do is tackle my big, daily rocks before I go to bed every night.

The rest takes care of itself.


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August Birch is an author, email expert, and entrepreneur from Michigan, USA. As a self-appointed guardian of writers and creators, August teaches indies how to make more work that sells and sell more work once it’s made. When he’s not writing or teaching, August carries a pocket knife and shaves his head with a safety razor.

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