How I turned my corporate skills into a business (step by step)

From in-house skills to self-made income.

Hi friends!

I’ve been receiving lots of DMs recently from new readers and the #1 question on everyone’s lips is ‘can you pretty please step through your corporate to portfolio career pipeline in detail?’. I’m not one to ignore repeated signals from my community so today I’ve decided to answer.

A little bit of context if you’re coming across my lil Substack for the first time:

• I spent my twenties working for big brands before leaving full time work 6 years ago to be a founder. Then I left that business in 2023 without a plan

• I started doing bits and pieces of fractional work and some freelance writing, and realised I could earn far more than a full time salary working this way

• I began writing on Substack about building my portfolio career because I thought others might be curious

• Now I have ~5 revenue streams across fractional, consulting, advisory, mentoring, and digital products and I’ve never felt more on purpose and on track

If you’ve been hanging around the Anna Mack’s Stack universe for a while then none of this will be new news, but if nothing else, hopefully today’s walk down memory lane gives you some fresh ideas for monetising your corporate, startup, founder or creative skills in new and interesting ways.

Let’s get into it!

1. I spent 6 years building my skillset in full-time jobs at Uniqlo and Mecca with a random stint in sales nestled in between. Desperate to learn, I was that annoying person putting their hand up for every new project. Helping on a photoshoot? I’ll do it! Building a sales forecast? Sure! Learning SQL? Me! Pick me! I was an eager generalist right from the start.

2. I started a podcast with two friends while working at Mecca. Two years into building that community, I quit my job to go all in. Learnt lots. Cried heaps. Made literally every mistake a first time business owner possibly could.

3. Moved back in with my parents at 32 years young.

4. Then I decided to leave my business to enter career limbo-land. I wasn’t sure what my next move would look like or where I fit. I questioned whether I was valuable or had anything to offer. Felt a bit broken.

5. Moved in with my boyfriend. Felt like an adult again.

6. I decided the logical next step was to tap the shoulders of everyone in my network and start looking for a job in the startup scene. I shamelessly emailed contacts saying “Hey, remember me? I’m available! Do you need help?! I can do anything!”.

7. Started interviewing for some full time roles.

8. Landed a couple of small clients and felt a flicker of hope pierce the shroud of my all-consuming scarcity mindset.

9. I still needed more work so I DM’d people on LinkedIn, had a million virtual coffees and said yes to everything. I told people I could help with Project Management, Operations, Marketing, Brand Development, Product Development and generally getting shit done. All of this networking and hustling felt a tad pointless until a few founders said they might have something coming up soon.

10. Attempted to quieten the fear and financial anxiety that was insidiously trying to make its way into every waking moment of my life.

11. Kept going.

12. I committed to writing for 30 minutes every single day for an entire year. Surprisingly a few essays came together and I wishfully pitched them out to some of my favourite publications. Got published once. Then twice. Then ten times more.

13. Realised I’d figured out how to monetise my writing.

14. Realised I’d created a second revenue stream.

15. Brain started ticking.

16. Two founder friends suddenly reached out asking if I was still available for work. One was in tech (an area I wanted to move into) and one was in beauty (my bread and butter), both were epic GTM projects. I said yes and a week later had the contracts in hand.

17. Took one big, long exhale because I finally had financial security for the first time in years.

18. I abandoned the full time job search and started viewing my career as a game of Tetris.

19. Diving headfirst into my fractional roles, I started documenting every piece of positive feedback and every time I added tangible value. This immediately reminded me that being a generalist is a huge competitive advantage.

20. Now in some semblance of a routine, I started a Substack and wrote about anything that tickled my fancy: almost becoming a spy, snapping my ACL, accidentally being a micromanager (oops), being alone in the forest for 48 hours, my new love affair with Taylor Swift.

21. Got over my morbid fear of ex-colleagues laughing at me and started sharing my Substack to LinkedIn.

22. I began thinking about income diversification more strategically, and tested a bunch of mini offers by seeding them out to my network. All but one flopped.

23. About a year in, I realised that I’d been working every single day for 3 months. Felt run down. Felt overwhelmed. Realised my people-pleasing tendencies, inability to say no and desire to over-deliver was killing me. Learnt that the line between freedom and burnout is razor thin.

24. Said goodbye to one of my first and fave clients.

25. A few months later I wrote a fateful post about my decision to exit traditional work and build a portfolio career. It hit a nerve and my subscribers skyrocketed. I connected with hundreds of others who were Tetris-ing their way into an unconventional career and life of doing cool shit with cool people.

26. Pivoted in public. Thought in public. Learnt in public. Built in public.

27. My DMs started blowing up with readers asking to pick my brain about portfolio careers. I caught up with many people before realising I could charge for my time. I started ideating a formal mentoring offer.

28. Because of this, 18 months into my post-founder journey I was forced to think through my positioning for the first time (better late than never). How should I communicate my generalist skillset? Can I tell people that I work with startups and mentor portfolio careerists without looking like I have a split personality? Can I stand for two things? Who does that?! Do I need a website? What the F will it say?

29. Determined to make it work, I did a full audit of the skills, experience and expertise I’d developed in corporate, as a founder and through my fractional work. I drafted my positioning. Started shaping my story. Created case studies. Built a website. Hit ‘update’ on my LinkedIn bio.

30. I launched my mentoring offer and wrapped up my highly lucrative tech gig so that I could go further into the portfolio career rabbit hole.

31. Had a lot of self doubt, drank a lot of wine, dreamt about the future, wondered if I’d make it.

32. I considered other ways to support my growing community and dangled some new product carrots to see if there were any bites. There were.

33. I launched the Portfolio Career Operating System with 6 weeks of early bird pricing. I worked nights and weekends to market the OS, iterate on the product and support my first customers through onboarding. Barely slept.

34. Learnt that passive income is a lie.

35. After a hectic few months I wrapped up my last fractional client to focus on my product pipeline. I tested a paid community, launched another digital product and started beta testing a portfolio career cohort.

36. I started receiving invites to speak at conferences and events about portfolio careers, creator business models and the future of work.

37. Wondered how I got here.

38. Remembered that it was by building up my skills, rediscovering my value, doing my very best and never giving up.

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Diving deeper into a few lessons I’ve learned along the way:

• A hard experience (being made redundant, having a career crisis, moving back in with your parents lol) is often setting you up for something great

• Intentionally documenting positive feedback from your peers is a great way to start building your value proposition

• People asking to pick your brain is a solid signal to spin up a paid service

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🫶🏼 When you’re ready, here are three ways I can help:

• The Portfolio Career Operating System: a fully fledged system for people who do multiple things and want to do them well.

• Spin Up A Mini Offer Playbook: steal my process for designing, launching and testing a new income stream in under a day.

• Portfolio Career Mentoring: 1-1 sessions to help you get started and build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.

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…to help you build a financially lucrative and creatively fulfilling portfolio career and life.