8 Things I Wish I’d Known Before Embarking on a Portfolio Career

If you’re a multi-passionate solo-preneur who’s:

  • Had a great corporate life, but it just isn’t enough anymore.

  • Wanted to do your own thing for ages, but never had that big, bold idea.

  • A fast learner who gets bored easily.

  • Professional and committed, but you can’t do just one thing for long.

Then you’re a prime candidate for a Portfolio Career!

Portfolio Career defined

A Portfolio Career is a professional and lifestyle choice where you integrate what motivates you, offers the most job satisfaction and brings you joy, into your work.

Unlike conventional careers, you hold multiple roles at the same time, so it’s often called a plural or slash “/” career (as in Writer/Board Advisor).

It could be a side gig tagged on to a day job, or you might be ready to jump into a full portfolio that consists of those multiple, possibly unrelated activities. Regardless of how you run it, you call the shots.  

However, it’s easy to think that the grass is greener and jump into a portfolio career without preparation and thought. I did that and boy, did I learn things the hard way. To help you prepare for your own journey, here are 8 Things I Wish I’d Known Before Embarking on a Portfolio Career,:



One of the biggest questions before you launch a Portfolio Career is “Where do I even start? I want to leave my job, but it’s defined me for 10+ years, and it’s a little scary out there!”

I totally hear you. Yes, I took risks with my career by transitioning into fields and roles that seemingly had little to do with one another (resulting in my moniker “The Career Adventurist”), but stepping out of the corporate world to launch my Portfolio Career was kind of terrifying.

After some trial and error, my first BIG realization is that a Portfolio Career is by its very nature self-defined, so the best place to start thinking about what to do and how to do it is with you!

Some questions you could ask yourself are:

  • What are my strengths, needs and motivations to do this? What makes this SO IMPORTANT that I MUST do this?

  • What aspects of my career have brought me the most joy and that I could do over and over again, in some shape or form?

  • What brings out the best in me at work? When am I most self-motivated?

  • What is meaningful to me in life? Is it health, relationships, wealth?

  • Based on my own experience, what do I want to bring to the professional or personal lives of others?

  • Which community, industry, or group of people could I add value to, and absolutely love the process of doing that?



Having worked in different industries and roles without having to apply for a job, I thought that I could rely on my “luck” to get projects and consulting roles that I’d enjoy right off the bat.

To some degree I was right, but then my pipeline began to dry out. That’s where I learnt that some planning would have made my foray into Portfolio Careers that much more enjoyable!

Here are some prompts to think about your plan:

o   When do I want to take the leap into a Portfolio Career?

o   How do I want to take the leap? Jump right in, or test the waters?

o   Who do I need to speak to know where to start, and to get my clients?

o   What support do I need e.g. a coach who’s been there, done that?

As a Career Adventurist you’re a solopreneur, so you need to strategize and plan like a business owner. Put those strategic skills to good use!


When I first began, I used to lament that my experience was so diverse that I didn’t know where to start. Slowly, I found out that Portfolio Careers are about micro-niches: unique, narrow areas of specialisation with a very specific audience.

And the unique thing is that you can have more than one micro-niche and they don’t have to be connected or related by anything other than YOU.

Here are some examples of that in action:

  • A former banker who works in holistic health therapy and physical training.

  • A former CEO who sits on a theatre group Executive Board, manages an investment fund and coaches at a business school.

  • A former Head of Marketing who writes for a business magazine and consults for lifestyle business start-ups.

Your micro-niches should center around the key skills, passions, and people that you really care about. So put on your thinking caps, and start imagining your unique combo!



I used to freak out at the thought of attending networking events. Even though I can be quite outgoing, meeting a random bunch of strangers and swapping business cards was NOT my idea of a fun night.

Through the years, here’s what I learnt about networking in a way that’s fun, non-cringey and that works!


Non-cringey networking  is about building relationships, not speed dating. What you want here is a deep bond with a selected few whom I call “Mavens”.

You’ll know these people when you see or meet them. They’re well respected by their peers (ideally your clients), well connected, and have a positive influence over wide and diverse groups of people.

Take the time to establish an authentic relationship with these “connectors” in your immediate network. Their wide network becomes your indirect network of loose ties… and this is where the magic happens.


Good news for the introverts reading this. You don’t need to be sales-y, have the loudest voice or act like a phony best friend to random folks you’ve just met.

The SECRET is to “be interested, not just interesting”.

The point is simply to have conversations about who you are, what you do and how you can help. In order to do that well, you must be interested in the person you’re speaking to.

Ask what your ideal client or Maven wants, needs, and dreams about. What are their pain points? What would really help them?

You’ll build trust and a genuine understanding of who they are. At the same time, you’ll gain such a well of knowledge about how to work with them and their network.



Another thing I wish I’d known before launching my Portfolio Career was how I needed to structure my time and manage my energy wisely to juggle different projects, commitments, tasks and deadlines.

My top strategies for success (and to maintain your sanity!) are:

i        Chunking: Chunk your time, allocating specific days for specific clients, and specific tasks or activities.

ii      Boundaries: Communicate your availability to others and hold firmly to boundaries while delivering on your promises!

iii     Saying No: Beware the lure of “bright, shiny things”. These could come in the form of activities that fill the wallet, but take time away from the important stuff (i.e. Portfolio Career building!).

iv     Energy management: When embarking on the portfolio career path, it’s easy to get super pumped up about the new adventures that lay ahead. But remember that energy levels need to go up and down. We can’t stay “on” all the time or we will burn out from the very thing we started to avoid corporate burnout.

Remember to pace yourself and cultivate more awareness of how you are feeling: body, mind and spirit!



Right now, I manage eight email accounts that I monitor and respond to almost daily: three on Outlook and five Gmails! When I started, it took me almost 6 months to adjust to this split-personality style of working and this is what I learnt:

1          Inbox Management

·       Set expectations. Decide how to best manage multiple email accounts early on and set expectations with your partners, clients, and associates.

·       Frequency. Set times in the day for checking emails if possible. Push notifications are not your friend.

·       Calendars. Managing multiple platforms can be tricky. Google Calendars can merge, but Outlook sometimes doesn’t sync well with Google Calendars. The best way I found to manage multiple calendars was to have them all on my iPhone calendar.

·       Visual cues. Choose different backgrounds or header themes for each email account for a quick visual view of which inbox you’re working on!

2          Activity Management

·       Time tracking: If you’re paid by the hour, it’s not ideal, but that’s how a lot of us start. Toggl.com is a really handy tool to track time spent on multiple projects and clients.

·       Client and Business Development: If you’re starting out with 1 or 2 gigs, a Google Sheet will be enough. If you have multi-client roles like coaching, or a long-lead time project, then a simple CRM like Pipedrive.com helps.

·       Project management: My various clients introduced me to tons of tools, and here are the ones I like best:

o   Asana for project management

o   Slack and Telegram for group collaboration and communication

o   Trello for task allocation and tracking



When I started my Career Adventurist life, it initially felt absolutely liberating. Not surprisingly, everyone around me thought I was absolutely crazy. They’d say: “You’ve studied so hard to become a lawyer!” or “You’re in such a good law firm... what are you thinking?” over and over again.

Self-doubt crept in, and it really felt like I had an inner monster that I needed to battle.

Here’s a quick tip I learnt along the way to tame that inner monster: It’s there to protect you (from an evolutionary perspective)!  It is simply our brain’s way of highlighting potential danger zones to keep us alive. Once you can understand that, you can make a conscious choice of what to do about it.

Whenever I felt doubtful, worried, scared or pangs of regret, I could shine a torch at that inner monster and say to it: “Hang on. This isn’t real.” Then I’d go back to the reason I made this weird and wonderful career choice and hold on to that, until the monster evaporated.

Exercise and Mindfulness practices go a long way to building up more awareness of the monster, so you can say #KTHXBYE.



One thing I missed in the early days of starting my Portfolio Career was the external buzz of colleagues and the structured on-going learning at work that would keep me on my toes. It’s so easy to get comfortable in a Portfolio Career once you’ve gone past the initial adjustment.

I’m a big fan of Tony Robbins, arguably one of the most successful personal development coaches out there. His CAN-I model: Constant And Never-ending Improvement is one you must adopt to stay on your Portfolio Career game.

Pay attention to new trends and market needs and you’ll stay relevant and motivated.

Do also take stock of and assess how YOU have changed as an individual since you began this journey. A coach and community of others with Portfolio Careers will keep you grounded and self-reflective for continued success!

Hey, well done for reading all the way through! Phew!

I’d love to know how this article has helped you.

·       What have you learnt about yourself?

·       What ideas do you have about how you could begin your portfolio career?

·       What skills would you like to develop to kick-start your journey?

·       Who or what can support you on this path?

Each of these tips will be expanded upon in the newsletters, blogs and videos, and online courses launching in Q3 2019!


To schedule 30 minutes* with me to ask questions about getting started on your Portfolio Career – FREE - CLICK HERE!

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Avalyn LimComment