Often people who start portfolio careers are high performance people that want more and are fed up with the ways larger organizations do things. They see the waste, lost opportunities, and have the self-belief that they could do it better if given the chance. But if they’re not careful, they can fall into the trap of simply recreating the inefficiencies they’ve seen before, slowing their growth, limiting their potential, and ultimately leading to the same frustrations they sought to escape. 

So this final pillar of a portfolio career is a look behind the scenes at the kinds of systems and processes needed to get things done efficiently to earn more and work less. As operations will vary from portfolio to portfolio, I will focus on generalities that are helpful no matter who you are or what kind of businesses or side-hustles you're working on. They are:

  • Streamlined communications
  • Project management
  • Time management

I know it’s not a super sexy topic, but getting these three right is key to working smarter so you are free to work on the highest value work, grow your portfolio, and earn more money while having more flexibility than you could imagine. Failing to do it right, will lead to burn out - no exceptions. 

Always busy, but rarely productive

Today’s knowledge worker is almost never more than a few minutes away from sending or receiving some sort of electronic communication. So it’s no wonder people feel distracted and busy, but also feel like they’re not getting anything done, or end a day exhausted only to realize that they now have to start actually doing work. 

As James Clear puts it so eloquently, you need to be the designer of your world and not merely a consumer of it. Get off the email hamster wheel by building systems that allow you to stay focused and deliver quality work in less time.

There are so many automation and organizer tools out there now, and most are highly economical, if not free. And, yes, I know that those working for large companies with confidential data and strict data security requirements may not be able to use those tools. But I’m not talking about that. I’m talking about automating the processes and systems in your side businesses and enabling things to run on their own. The areas that you have full control.

If you want better results, then forget about setting goals. Focus on your system instead. (James Clear)

It’s not a bad idea to set goals (e.g. generate 1 million in annual revenue in 2025), but as Clear explains in his book Atomic Habits, it’s a lot more impactful to design a system that creates high output. 

Now, an efficient system is not developed overnight. Instead, it’s an iterative journey consisting of incremental improvements across the three areas I mentioned: communication, project management and time management. You may want to tweak this over time for your exact circumstance and skillset, but I would start with these three before getting too fancy. 

Now assume that each of the three areas have four levels of operational maturity: Seed, Sprout, Sapling and Sequoia. Using maturity stages helps you to avoid trying to do it all at once. For example, it’s unlikely you will jump from Seed to Sequoia, but highly likely you will move from Seed to Sprout, and so on. So this helps you to prioritize, to track your progress, all without overwhelming yourself or your team. 

1. Communication

1.A Seed So many of us conflate email with workflow and project management, so the first step in the seed phase is to do inbox triage so email is used for what it meant for - formal communication. Get the junk out of your inbox by unsubscribing and getting yourself off non-essential distribution lists. You can also set up rules to auto archive emails that do not need your attention but you would like to keep as a reference in case you need it in future. This can take less than an hour to setup, reduce decision-fatigue, and save countless hours of administration time and distractions. 

1.B Sprout Now that you’ve removed all your junk email and cut down your email traffic, the next step is to remove all non-client emails. I like to think that I only want to "see money" in my inbox: client-facing conversations, business development and sales. Move all other team emails to other channels like Whatsapp, Slack, Teams, or whatever chat tool you use. This is a huge unlock because it’s drastically reduces the amount of time spent checking emails and increases your time spent on revenue-add work. 

1.C Sapling The next stage for communication is to batch your emails using a tool like Boomerang which can release emails to your inbox 4 time per day. This way you know, for example, at 10am you have a batch of emails being released and for 30 minutes you will action, delegate or defer each email delivered by updating your project management tool, then get back to deep work. I appreciate this is a polarizing approach to email and doesn’t work in all scenarios. Nonetheless, think about it and which one of your companies this method can be applied. Batching your email time can be a huge productivity unlock by maximizing deep focus, and fights off email addiction (yes - it's a real thing).

1.D Sequoia The most effective teams at communication are ones that have adopted task-based communication. What this means is they’ve found a way to consolidate their non-client communications and project management coordination into a single tool. In doing so, tasks, milestones, risks and dependencies have notes and communications and templates and SOPs associated with them, and users can easily tag one another to ask questions and progress tasks seamlessly. If you haven’t already, there’s a great book that elaborates on this topic called A World Without Email (Cal Newport). The beauty of this system is that you can have reams of materials but avoid clutter from endless folder hierarchies and chat threads or emails. If you’re looking to test a tool, checkout Airtable or Monday.com. 

2. Project Management

2.A Seed At the seed stage, if you’re not there already, all you need to do is maintain a simple to do list. Keep this simple, simple, simple. As for technology, all you need is something simple like Notion, Google Tasks, Word or a simple notepad. Make it available offline so you can update on the run (on the train or bus, or wherever you are when that lightbulb moment occurs) and make it the first work-related thing you look at in the morning, and the last thing at the end of the day. Make sure you have a way to shuffle prioritization and highlight critical tasks.

2.B Sprout → The next phase of project management is to shift your To Do list to a proper project management app or tool. I’ve experimented with Trelio, Jira, Basecamp, Clickup, Monday, but my favorite BY FAR is Airtable. It’s easy to use with an awesome UX, and integrates into my websites, and I can create dashboards, restore previous versions, and is all round great for workflow collaboration. The mobile and iPad app is great for updating it on the move too. 

2.C Sapling The next phase of project management is if something is done more than three times by you or your team, there should be a standard operating preceedure (SOP). By writing this down, it forces you to think about whether you’re doing a task in the most efficient way possible i.e. it helps you be intentional about how work gets done. The other benefit is that it provides a knowledge base for your team so new hires can review the SOP and action. This way you’re building a “machine” that does the work instead of you just "doing the work" every time. 

Something I should mention is that it is almost always faster to just do the thing, than to build a template out of it. But if you want to grow and scale, you have to commit to the process of standardizing and templatizing, then delegating with confidence and focusing your time on the highest value work. 

If your curious about what AI is doing in this space, checkout https://checklist.gg which can auto-create SOPs.

2.D Sequoia → The next phase for project management is to let the code do the work for you. You do this by developing integrations and automated workflows across your companies including your CRM, invoicing, payments, knowledge materials and task management in one project management tool. Similar to the Sequioa stage of Communication, checkout Airtable or Monday.com as a starting point. 

3. Time Management

3.A Seed When it comes to time management at the seed stage, think about how your energy flows throughout the day. If you have no idea what I mean by this, observe when your energy level is high vs low. For most people, there are specific tasks or people we work with that lift our energy up. Equally, there are those that bring us down. When you figure this out, you will find creative ways to bundle high energy moments to maximize and compound their effect on you while minimizing and compartmentalizing the effect of low energy influences. 

One simple way to figure this out is keep a notepad near you for a couple of days and each hour note from 1 to 10 whether you are feeling high or low energy, then you’ll be able to connect your energy level to what you were doing at that time. Simple. 

As an example, I’m a morning person. I’m productive, motivated and focused after my morning coffee, so by understanding this about me, I prioritize my strategic work and relationships during this time and put in active steps like blocking my calendar and rescheduling non-essential and non-time sensitive calls outside of this window. 

3.B Sprout As a carry on from understanding your energy levels throughout the day, the next step is to customize your calendar to your optimal productivity i.e. take ownership of your calendar or someone else will. Failing to proactively allocate your time is basically telling the world you will allow anyone to come along and chop up your day - and flow - however they like, regardless of the importance or relevance of this work.

I use Calendly for scheduling to cut out the back and forth, and Pomedoro for time-boxing activities. I recommend allocating non-important calls to your low energy windows to protect your high energy window for deep, value-add work. You can also create multiple Calendly calendars where you provide a wider selection of time-slots for high priority clients, partners, investors and so on, and a more restrictive calendar for less critical calls. 

3.C Sapling The next level for time management is to lock your phone away. Put it in a draw out of reach and walk away. It’s too easy to grab and so many of us are uttlerly addicted to using it (whether we acknowledge it or not). The same applies to any other devices that are also distracting to you. 

3.D Sequoia The last maturity phase for time management is active calendar blocking in sync with your energy levels. If you can consistently do this, you're doing better than most.

Final Say

It’s easy to geek out about efficiency tools, but no tool is going to magically makes things operationally perfect. It really comes down to intention. Making intentional incremental improvements really do add up over time. The lowest hanging fruit is optimizing your inbox, then, if you’re able to get interested in the further enhancements I mentioned and commit to making 1% progress each day then you’re on the right track. Like putting money into your savings account, it may not feel like a lot till 6 months has gone by and you realize you started to build a machine that’s yours, high ROI and creates flexibility and freedom.