Last Update: July 23, 2020

With many folks sharing the start of their journey, others (like myself) become busier and fail to update as their online business grows. To counter this trend, I thought today would be a good time to share the key milestones along my journey to this point in my online career.

Perhaps you have seen similar milestones, or have yet to see them. Or perhaps your own journey has very different milestones? Please leave me a comment and let us all know!

30 Milestones in 5 Years

Here we go - as best as I can remember (accuracy might be hazy!)

  1. April 2015: Switched day job to remote contractor (performance based, no salary)
  2. September 2015: Joined Wealthy Affiliate (went premium a few weeks later)
  3. December 31st, 2015: Completed Online Certification Training
  4. January 2016: First request from external agency to post content on my site
  5. March 2016: First commissions from affiliate marketing
  6. March 23rd, 2016: Achieved profit from WA membership
  7. June 2016: Established a long term, freelance contract in digital marketing sales
  8. June 2016: Fired my boss - income now 100% online
  9. July 2016: Wrote my first training module on WA
  10. 2017 to mid 2018: Start brewing business in China, online business is reduced
  11. Mid 2018: Form a digital media company (the paperwork)
  12. November 2018: Take over digital assets of company I'd been freelancing for
  13. January 2019: Partner with a fellow digital marketer
  14. February 2019: Clients begin to pay into my new company
  15. March - April 2019: Difficulties in hiring and at odds with partner
  16. April 2019: Fire / pay out partner
  17. April 2019: Hire salesperson
  18. May 2019: Write mission statement, Re-design audience driven business model
  19. May 2019: Hire first content writer (content team formed)
  20. June 2019: First workcation (becoming a digital nomad)
  21. July 2019: The world gets disruptive (narrowly avoid the HK airport lock-in)
  22. October 2019? - First $10,000 month
  23. November 2019: Have been running a digital marketing company for 1 year
  24. December 2019: The world catches fire, business is tense
  25. January 2020: The world goes to hell, business is very tense
  26. April 2020: Business is growing as events being replaced with digital advertising
  27. April 2020: Give away $5,000 in monthly ads to assist the businesses in my niche
  28. June 2020: First $20,000 month (in revenue written, not 100% realised in June)
  29. July 2020: My company finally starts losing business due to the Pandemic
  30. July 2020: Almost all tasks outsourced

Where I am Now

So there we go! 30 milestones in 5 years. I now run a small but moderately successful media company, recognized by the majority of companies operating in my niche. I have 3 people working for me, and as of Monday, my primary role is management and my secondary role is sales.

Where Next?

With this latest hire, my time is freed up for new digital projects. I have been planning this next step for the past 3 years, and I finally have the time and money to make it happen.

It's been a crazy journey, but so far it's led me to a good place and I'm super excited to share the next stage of the journey with my Digital Marketing team and my WA family!

Your Milestones

Have you passed any of these milestones? Are you looking at any coming up in the near future? Please tell me where you're at, and I'd be happy to share my experiences in depth with you.


-R. Kingsley

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Recent messages
JMatonge1 Premium
These are well-tabulated milestones. They are also a good way of encouraging many people on this platform. Congratulations.
RKingsley Premium
Milestone 31:
Wealthy affiliate can no longer support my business and I have to leave for a better web host.
JeffreyBrown Premium
Very nice, indeed!

RKingsley Premium
Thanks Jeff
JeffreyBrown Premium
You're very welcome!
soldiersam2 Premium
Thanks for the post bro! I liked to look at successfully timelines; somebody told me that it leaves clues.
RKingsley Premium
Thank you, that's what I'm hoping! Have you seen any similar milestones?
soldiersam2 Premium
Not yet in this forum. Sometimes effective people will give glimpses of their journey on Youtube. Other than that seems like you just have to read about people from the past.
Dejosef Premium
You should be incredibly proud of yourself.

if I reach half your list I'll be happy, (especially Oct/19)
Well done again, reading your milestones gives other people hope, (me included).

All the best Kingsley.
RKingsley Premium
Hopefully you'll be able to look at this list as points to watch for in your own journey, so you know what's coming up next!
JKulk1 Premium
Hi Jesse.

Your story is an inspiration to many.

These days I'm a retired person and anything I achieve in my retirement years is simply a bonus.

If I had to write down my milestones it would take up far to much room in the WA platform. One day I'll write a book.

I love the frank and honest way you have written down your milestones. They make for a great read.

I wish you all the best for the future, along with many more successful years.

All the best. Jim
RKingsley Premium
Thanks Jim!

Are there any here that look the same to you? I'm super interested to see if this is a typical journey, and if not, what do the similarities look like?

This might give myself and others here a cheat-sheet to success, by identifying the key steps beyond the basic training... maybe.
JKulk1 Premium
Yours has obviously been a long term journey my friend. I think that on its own is rare so I probably wouldn't call it 'typical'.

There are others that have success stories here that are probably similiar in some aspects, but very different in others.

I did write a blog Mentioning a few of those that I know have turned affiliate marketing into a full time business.

Those that come to mind are Nathaniel, Zed from Smartketeer, Grace from littlemamma, Jerry Huang, Israel, Jay from MagiStudios and many more that I can't think of off hand.

As far as any extra traininv is concerned I don't mind paying for this from platforms such as Udemy.

I'm currently completing a course there on building an e-commerce site.

I also completed a course of Jerry's there that covered how to look for and outsource blog writing.