Portfolio Career: Working on Multiple Businesses at the Same Time


I’m now at the stage in my career that I can focus on whatever projects excite or interest me. It also means that I can focus on several projects and businesses at the same time. I have what is called a portfolio career. I.e. I have a portfolio of work jobs, such as:

  • This blog and related repurposed writing
  • Coaching
  • Sales Agent for packaging automation and infra-logistics
  • Property investing

This is rewarding and is something I always aspired to achieve, however there are some downsides. One of which is how to manage my time or more specifically my focus. Common wisdom says you should concentrate on one thing at a time. This, however, would mean dropping some projects I am passionate about.

So, I investigated various methods of managing my time and here are three methods to manage a portfolio career.

1. Work on Each Business Every Day (Time-Blocking)

This is a terrific way to maintain momentum on all the different projects and businesses. It is also good for when you have to perform regular and frequent activities. For instance, in my sales agent business I have set myself the target of reaching out to 20 prospective customers per day. I can usually complete this in a couple of hours.

A batching method would have me saving up all these calls/emails for one day. For instance, making 100 contacts in one full day per week. To me that would be draining, but 20 per day is achievable.

You can read more about how I structure my time for cold calling in my post My Prospecting Process. In it I walk you through how I go about gaining new leads.

The other advantage of the time blocking method is that you can give yourself plenty of variety throughout the day. For instance, writing for 30 minutes, then making sales calls. I can keep the afternoons free for exercise, home projects or ad hoc work.

How to use the Time-Blocking method.

The first thing to do is to block out specific time slots for each business or project daily (e.g., Business A: 9 AM–12 PM, Business B: 1 PM–4 PM, Business C: 8 PM–9 PM).
Next, within each time slot you can prioritise deep work in the most productive hours. For instance, I am more energetic between 10am to12pm, so I can save any creative tasks to be done then. I am more sluggish in the afternoon, between 3-5pm so I will save exercise or low focus tasks for then.

Potential Downsides of time blocking

Sometimes, frequent context switching can reduce efficiency. Research at the University of California has shown that once you pause one project, it takes you 23 mins to get back to full flow once you re-start. For this reason, this method can slow down progress on long-term projects. For instance, when I am drafting a book, I would prefer to spend good, focussed time on the task, to immerse myself in the project.

2. Dedicate Different Days to Each Business (Day-Blocking)

The second method is to do day blocking. This method is favoured by such luminaries as Elon Musk, who seems to get plenty of stuff done. (I have no comment on the quality of said stuff).
The benefit of this method is that each business/ project gets deep focus time. You can also use it for long-term planning.

If you prefer batching similar tasks for efficiency, this can also be a good method. For instance, if you didn’t mind doing all your sales calls in one day, contrary to my preferences.
This method is also better if your businesses are unrelated and switching every few hours feels mentally exhausting.

How to do use day-blocking

Firstly, assign full days to each business or project (e.g., Monday for Business A, Tuesday for Business B, Wednesday for Business C and so on).
You can also use overflow days or flexible catch-up time if needed. For example, you can leave Fridays free for this. If there is nothing that needs attention on Friday, great have the day off.

Potential Downsides of day-blocking

If one or more of your businesses require daily attention, making full-day separation would be difficult. If one of your businesses involves responding to emails or taking phone calls, your prospective customers may not appreciate having to wait until next week to get your reply.

The other reason day-blocking fails for me is that if an urgent task arises, it will disrupt my schedule. There’s nothing worse than having a full day planned out to work on a long-term project only for this to be scuppered by something unforeseen. Surely there must be a better method which uses the best of both worlds – time blocking and day blocking.

Yes, there is: the hybrid approach.

3. Hybrid Approach (Best of Both)

With the hybrid approach, you can get the benefits of time blocking, in that you can gain momentum on all of your projects, plus be able to react to any unforeseen emergencies that arise. It also gives you a varied day, so that you don’t burn out on one project. You also get the benefits of day blocking, so that you can have that deep focussed time you need to ‘break the back’ of big project.

How the hybrid approach works in a portfolio career

I spend my mornings on deep work for one business; Then I spend the afternoons managing lighter tasks for the others, or general tasks. For instance, deep work on the mornings (9-12) of Monday for Business A, Tuesday for Business B, Wednesday for Business C. The afternoons can be spent on the smaller routine tasks for each business or project for instance, emails, phones calls, editing, firefighting. I can also use this time to catch up on all those ad hoc, ‘loose’ tasks that aren’t related to anything. If I’ve finished my work early in the afternoon, great, I take the rest of the day off and maybe go for a walk or read a book.

With this hybrid method you can still use dedicated days for strategic planning or big projects.

Ultimately, managing a portfolio career isn’t about rigidly sticking to one productivity method—it’s about finding the rhythm that works best for your lifestyle, energy, and goals. Whether you thrive on the structure of time-blocking, the deep focus of day-blocking, or the flexibility of a hybrid approach, the key is to stay intentional and adaptable.

A portfolio career offers incredible freedom, but that freedom only becomes sustainable when balanced with smart systems. Try out these approaches, tweak them as needed, and remember: the beauty of a portfolio career lies in the ability to design your own way of working.

I’d love to hear how you structure your day. What’s worked for you?

Leave a Reply

Your email address will not be published. Required fields are marked *