Skills you need to run a successful one (wo)man show.

The Portfolio Career Explained, Part 4

My current status: soaking in history and bathing in ramen in Japan.

Building a portfolio career that involves multiple jobs, clients, projects and income streams is pretty wild when you think about it.

I own a business but I’m not a traditional founder. I don’t have employees or investors, or any of the fanfare that comes along with building something huge, but I have infinite earning potential and the freedom to choose what I work on.

On the flip side, I have ongoing clients and regular commitments but I’m not tied to a full time job. I don’t have annual leave or a guaranteed paycheque, but with locked-in retainers and while building scalable revenue on the side, I sleep easy knowing I can put food (and wine) on the table.

While designing my portfolio career I’ve strategically cherry picked the best parts of both worlds - the financial security of a job and the freedom of not having one. I appreciate this sounds like a dream and in many ways it is, but it’s taken a lot of experimentation and up skilling to get here. I’ve learnt how to create, sell, network, write, manage my time and energy, focus, get out of my own way and switch off. Along with these obvious skills, there are a few unconventional ones you need too…

1. Thinking and acting like a CEO.

As a solo operator, there’s only one CEO in your business and that CEO is you. You’re the visionary, leader, manager, storyteller, decision maker, do-er and sales guy. Over the years I’ve learnt to:

• Steer the ship, even if that ship is just a one person canoe

• Make quick decisions 99% of the time with incomplete information

• Make slow and considered decisions the 1% of the time that slow, considered decisions actually matter

• Actively celebrate the wins and reward the team when they do well (*cough* the team is me *cough*)

• Make it my responsibility to understand the numbers

• Ask for help when I need it because if I don’t, I’m acting as a self sabotager not an inspiring leader

• Challenge myself to uncover what I’m not seeing or understanding in a situation

• Take ownership of my questionable behaviour, failures and mistakes, no matter how much I want to blame the environment or other people

• Seek to understand how I’m complicit in creating the circumstances I’m not happy with

The only way I’ve been able to create a new life for myself is by taking ownership and responsibility over every single piece of it. This is what having a CEO mindset is about.

2. Taking radical action on high leverage tasks and building systems to minimise low leverage ones.

Not all tasks are created equal, and as a solopreneur with limited time and energy it’s my responsibility to identify which tasks will keep working for me long after I’m done.

High leverage tasks are force multipliers that compound, where one unit of effort equals more than one unit of output. Hiring a brilliant personal assistant and delegating to her effectively, writing this newsletter, and meeting new and interesting people are all high leverage tasks. Here’s why:

• Spending one hour briefing my assistant to manage my personal inbox reduces the time spent on emails by hours

• A single newsletter might drum up three new mentoring clients

• One coffee catch up has led to a new and exciting collaboration

On the flip side, low leverage tasks have a one to one ratio: one unit of effort equals one unit of output. Getting to inbox zero, managing my calendar and attending meetings with no objective are all examples of low leverage tasks that I a) don’t do, b) delegate, c) automate or d) batch and smash them out in one hour if I really have to.

As one little human being I only have 24 hours in a day but I do my best to turn 8 hours (roughly) of work effort into hundreds of units of output by identifying and focusing on the areas that compound. I then try to build systems to minimise everything else.

3. Understanding that different situations and problems require different types of hard work.

A lot of people peddle the narrative that the only way to make progress is through violent and relentless action (if I’m honest with myself, at times I’ve been part of this problem, my bad). Doing more things for longer will get you to where you need to be, right?

Wrong.

Shane Parrish from Farnham Street explained this better than I ever could in a recent blog. He wrote that there are many different kinds of hard work:

1. Outthinking (a better strategy, a shortcut)

2. Pure effort (working longer, intensity)

3. Opportunistic (positioning yourself to take advantage of change)

4. Consistency (doing average things for longer)

5. Focus (saying no to distractions)

He argues that pure effort isn’t the only way to make progress despite many of us thinking it is. I agree, but in my mind this list is incomplete. Here are my additions:

6. Creating (clocking off to take a break and allowing your brain and mind to wander)

7. Experimenting (testing new and different ways of doing things to see if they generate better results)

8. Saying yes (identifying opportunities that will move you forward and grabbing them with both hands)

9. Stopping (walking away when something clearly isn’t working no matter how many times and ways you’ve tried)

As a solo operator I’m making judgement calls daily about how to spend my time and direct my effort, and what approach to problems I should take. I don’t have a big team or big budgets so I need to work smarter. I’m forced to think critically. I must tailor my method according to the situation at hand.

4. Listening deeply.

Connecting with people is at the heart of building a portfolio career, and the best way I’ve learned to connect is by listening with intent.

When I’m selling, I’m listening to the prospect’s problems to see if I’m well placed to solve them. When I have a casual coffee, I hold space for the other person to speak about whatever is on their mind. When I publish, my ears are open to receiving feedback and learning what resonates and what doesn’t.

It’s easy to think that running a one person show involves speaking, projecting, shouting and promoting. And while there’s certainly a bit of that, listening is the key to opening up real connections and doorways.

5. Not panicking.

Problems are a-plenty when it comes to working for yourself. One day you may have three retainer clients, the next day you might have none. A product you’ve spent months creating doesn’t sell. Your website crashes. A deal falls through. You screw up your tax and get slapped with a huge bill. You don’t get paid on time. Or ever.

Some or all of these situations will occur (read: all of these have happened to me) and I’ve learned that the key is not to panic. I can’t navigate my way through a storm if I’m freaking the fuck out, so instead I breathe. I lower my heart rate. I take a considered step forward and exit stage left from the mess.

6. Becoming increasingly self aware.

A portfolio career inhabits the best things about being a founder and an employee but it can also bring about the worst. You can’t escape the fact that uncertainty always lingers slightly to the side, right next to comparison and self doubt and imposter syndrome. To help balance this out I’ve prioritised and invested in my personal growth: I journal, have an Executive Coach and go to therapy. I’m always asking myself the important questions:

• What are you trying to achieve?

• What are trying to optimise for?

• How much time are you spending on bullshit?

• What invisible belief systems are impacting your behaviour (or lack thereof)?

• Where do you deserve to be promoted?

• Where do you need to be fired?

You can’t build a successful one person business if the person behind it is falling apart.

Anything can be learned.

There are hundreds of skills that will set you up for a solid portfolio career, but the good news is that even if you don’t have them yet, it doesn’t matter. They can be learned. They can be cultivated. They can be built.

I didn’t exit the womb thinking like a CEO. I used to grind and grind and grind and grind until I pushed myself into the ground. Panic used to be my middle name.

Only now, do I know what it means to take ownership over every action and decision in my life. Only now, do I understand the nuances around hard work. Only now, do I have the skills to calm my nervous system when the rug gets pulled out from underneath me. And while I still have a long way to go, only now do I understand that while I can’t do everything, I can learn anything.

So can you.

And if you ask me, that’s an exciting place to be.

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This post is part four of a seven part deep dive into Portfolio Careers:

1. Saying cya to “traditional” work, and why I’m building a portfolio career instead. Read here.

2. WTF is a portfolio career? Read here.

3. How I’m building my portfolio of clients, projects and income streams. Read here.

4. Skills you need to run a successful one (wo)man show. This post.

5. One thing they don’t tell you about working for yourself. Read here.

6. To portfolio or not to portfolio, that is the career question. Read here.

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👀 What else have I missed?