Website Income

How I Quit My Job to Pursue Online Entrepreneurship Full Time so I can Ski, Bike and Hike With My Family

This post took ~8 years to write!

It is with great satisfaction I announce that the goal I set for my family has now been achieved and I have left my 9-5 7am-6pm day job to pursue online entrepreneurship full time!

First let me say thank you to everyone who has been following me on this journey you the readers of authoritywebsiteincome, customers of LightningRank, friends, family and my wife.

This is the start…big stuff to come!

This post covers…

Why Did I Want to Quit my Day Job?

For everyone their reasons are a little different. Some people want to become digital nomads mine came down to wanting to…

  • See What I Can Do on My Own – Online entrepreneurship has a lot of opportunities I am excited to explore. I may or may not regret this decision but I am 100% certain if I never took a shot at building something on my own I would always regret it!
  • Ski/Bike/Hike With My Kids (my wife can come to 😉 ) – My youngest child will be 36years old when I retire at 65 (4 years older than I am now) and the number of hours I work per day between now and then were not going to go down based on the path I was on. But the main reason is I simply want to ski, bike and hike with my family in my hometown!

This Table Scared Me!

Green = Years Worked at Day Job

Yellow = Years Left to Work!

My Age at Retirement = 65 & My Oldest Kids Age = 36

One of My Main Reasons Explained with Pictures...

(my reason why explained with pictures!)

How Did I Get Here – My Online Business Building Timeline

  • Pre University – Side Hustles
    • Lawn Cutting 
    • Selling Skis on Ebay
  • 2004 Went to University (Mechanical Engineering with a Business Minor)
  • 2005 – Bought International Edition Textbooks from India at 90% Off and Sold for 75% off to friends
  • 2005 Started listening to AudioBooks and a few had significant impacts on how I thought about business/life options.
    • E-Myth Revisited 
    • Rich Dad Poor Dad 
    • The 4 Hr Work Week
  • 2006 – Started a Bike Parts Company – Never Manufactured a Part
  • 2007 – Started a TextBook Selling Website – Sold One
  • 2008 – Got Engaged
  • 2008 – Worked for a technology startup company and was responsible for getting their site built (cheaply)
    • Learned about ODesk (now upwork) (blew my mind)
  • 2008 – Started a Small Membership Site That Organized Old Time Radio Shows – Cost $2,000 Made $150
  • 2008 – Built a Sales Page to Sell Excel Templates – Started making a few sales – $100/month
    • Learned about article marketing
  • 2009 – Built some “Feeder” WordPress Sites to Drive Traffic to Sales Page – $200/month
    • Learned about SEO 
    • Learned about wordpress
  • 2009 – Graduated with a Mechanical Engineering and Business Degree
  • 2009 – Started Working in Project Management for an Oil and Gas Company
  • 2009 – Started replicating the “feeder” sites and made them into money sites – $750/month
    • Outsourced everything article marketing, web creation etc. 
    • The dream of a self growing fully outsourced system was strong!
  • 2009 – Got Married
  • 2010 – Attempted to build a Facebook Team Gift app after coming up with the idea at my Bachelor party with friends– FAILED – $1,000 gone
  • 2010 – Built a team on ODesk to promote each website using Yahoo Answers and Blog Commenting – $1,250/month
    • Built the team up to 15ppl
  • 2011 – Stopped Being Profitable & Cut Back On Team To Become Profitable – $500/month
  • 2011 – Started Building Private Blog Network and Testing Other Strategies to Improve Ranking and Drive Traffic
    • Feb 2011 – Panda hit – No Impact on My Business
  • 2011-2012 – Started focusing on lower quality exact match domains that required less work and my team was building 2/week – $1,500/month income
    • Never used “automated” link building methods! 
    • Never used spun content on my sites (but yes I was one of them that used it on article sites)
  • Apr 2012 – Penguin hit – Small Impact
    • Doing some research and trying to think about SEO like Wayne Gretzky played hockey “go where the puck is going to be not where it is” translated into “give the search engines what they want not game the current loopholes”
  • Summer 2012 – Decided to shift focus to build up my larger more useful sites – $3k/month
    • Sites like grew to 800 visitors/day
  • Aug 2012 – Decided to create a public case study through showing how I was going to build (My Case Study Website URL is Now Hidden)
  • Sep 2012 – EMD Update Hit – 15%-25% of my sites got killed(all smaller sites) – 5% of my earnings affected – $3k/month
    • EMD update reconfirms I believe I am on the right path with larger more authoritative sites.
  • 2013 Feb – (My Case Study Website URL is Now Hidden) averages over $1000/month for month 6, 7 and now can make up to $8k/month income (sold website for six figures)
  • 2013 Aug – Began using PBNs to rank my websites and grew my passive income portfolio – $6k/month income
  • 2013 Nov – Based on my on my monster post Ultimate Expired Domain Guide I launched my PBN creation service – $10k/month income
  • 2014 – Continued to build my passive income portfolio and my services business – $11k/month average
  • 2015 – Focused on systematically growing my passive income portfolio which grew to $14k/month for its best month (reliably now making over $10k/month)
  • 2015 Sep – Added FBA Business model to my strategy for Q4 2015 – $24k/month average
  • 2016 Jan – Listed FBA business for sale
  • 2016 Feb – Launched as a partnership
  • 2016 Feb – Let my day job know I will be leaving!
  • 2016 Mar – Started with Private Equity group to rinse/repeat affiliate site to FBA business conversion
  • 2016 May – Launched as the first/best Amazon Listing Hijack Monitoring service
  • 2016 June 10th – Last Day of Work!

Top 3 Inflection Points in My Journey

  1. Finding Out I Will Become a Father – Narrowing in on my “why” in 2013 gave me the drive to stop messing around with simple low value add crap and really do the hard work, add value and consistently grind. When we became crystal clear on our goal of $15k reliable income and moving to our hometown to spend time with family the business started to move in the right direction quickly!
  2. Creating an EPIC Guide (Adding Obscene Amounts of Information/Value for Free) and then listening to the audience and providing services around that topic was another large inflection point for the business.
  3. Unit Shutdowns at Work & 80+hr Weeks – This was actually a deflection point but was equally insightful. There were multiple times over the last few years where I worked 80+ hr weeks for a couple months back to back and it became clear the business suffered after that time when I wasn’t able to work more than an hr a night. Based on this it was clear that my time, despite all the systems I had put in place, still significantly influenced the direction of the business. Despite the promise of systems replacing me completely it was clear that for my business more time = more success.

Highlighted Yellow Represents 80+hr Weeks at Day Job

Why Didn’t I Quit Sooner?

  • I had very specific metrics to hit for both income and runway before pulling the trigger…
    • Income – I had a very public goal of hitting $15k/month in reliable income by the age of 35. This had been achieved for several months but it took awhile until the second criteria of runway/mortgage was achieved. 
    • Runway/Mortgage – In addition to the public income goal I also had a runway/mortgage goal to ensure I wouldn’t need to play defensively in my online business.
  • I was learning a lot – My belief was that this game is a LONG game (just look at the graph to 65 above)! I don’t see me ever not doing something associated with building a business and as a result I believed that the most important thing right now is to improve my abilities and one of the most profitable/systematized corporations in the world certainly had many great learning/development opportunities. My online business is better for the experience I had at my day job and vice versa, I was a better employee because of what I was learning in my online business. The learning curve had started to slow over the last year and that contributed to the decision around timing.
  • Enjoyed a lot of my day job – My day job as a plant shutdown manager / maintenance team leader had a lot of great aspects. I worked with very capable people and we were thrown at some very challenging problems with a lot of pressure (such as being on point and responsible for 100+ contractors fixing equipment that was loosing the company $1M/day being down).
  • I wasn’t sure if online business would be fulfilling – Online business can be played at different levels and where I was originally playing it was not fully satisfying. Systematically building authority websites is kinda fun from a systems standpoint but it wasn’t really challenging me on multiple levels. However, lately with the addition of some new businesses and partnerships it has become clear that I can be as challenged as I choose to be with my online business and that is exciting!
  • Increasing my chances of successfully exiting and not returning was more important than getting out early – My wife and I had many discussions on the right timing to pull the trigger. In the end we both believed that the prize on the table (moving back to our hometown) and staying there was substantial enough that ensuring when we did pull the trigger the chance of success was as high as possible!
  • Diversifiable Income – No single point of failure could exist in my business that would ruin it. I wanted to be certain that I had multiple channels of income that would support my family. My business needed to be a multi-legged stool with each leg of income being somewhat separate from the other. If any one leg got chopped out the stool won’t fall!
  • Golden Handcuffs – The pile of money between pension, career trajectory and vesting bonuses that has been burned by me leaving is not inconsequential. Although I left on very good terms with the door being open for me to return the amount of money being "burned" certainly had the desired effect of being slow to make the move.

So… How did it feel to Quit?

I enjoyed working with most of the people I worked with and my direct reports and manager were all exceptional so I did feel a little guilty about leaving them. In addition I had made some great friendships over the last 7 years and as part of this change I will be leaving my current city.

However in the end it felt awesome! This was a goal which became an obsession for the last few years and achieving it was incredibly satisfying for everyone involved!

My manager was incredibly understanding and treated me much better than I had expected.

One interesting note was that all the coworkers that I considered as really strong performers were positive/encouraging while many of the “B team” employees were scared for me and couldn’t understand giving up the security!

5 Most Important Lessons I Learned

  1. Do the Hard Work - For the first few years online I was in search of the easiest way to make money online. WRONG! When I buckled down and did the “hard” work usually the type that made me uncomfortable results followed! Many nights I wanted to lie down and watch TV exhausted from 12hrs of work, playing with kids for 1-2hrs but if I had I wouldn’t be writing this post.
  2. Have a CLEAR Driving Goal & Reason Why – It wasn’t until I was crystal clear on my reason why that the business moved in the right direction quickly.
  3. Add Value and Don’t Look for Shortcuts – Shortcuts online don’t exist, stop looking for them! The only way to make money online is to add value. The more value you add the more success you have. No, this rule doesn’t hold 100% of the time but believing it 100% of the time is a recipe for success.
  4. Take Massive CONSISTENT Action – Every night/day that you do work, if you are adding value, you are pushing on the flywheel of your business. When you take time off from the work the wheel starts to slow…consistent massive action on an activity that adds value to people is bound to result in success.
  5. Don’t Do It Alone! – From my first popular guest posts on other peoples sites (like Spencer Haws) to my most recent partnerships with industry leaders (like Scott Voelker) and previously little-known experts (like Andrew from it has been clear that building an online business is more fun and successful when working with others. In addition to these relationships my team has been a huge factor in the businesses growth. Some of my team members have been with me since the start including some whose income has gone from $1/hr to $7/hr and another who named me as a god parent…

3 New Concerns I Now Need to Manage

With changes come new challenges, to be honest these I am afraid of and I won’t know if I overcome them or not for a couple years. I hope AuthorityWebsiteIncome and my monthly reports will help me have the discipline to ensure these fears don’t become a reality.

  1. Getting Mentally Soft – For the last few years my schedule has been a little bit insane. Approx schedule… wake 6am, leave for work 6:30am, work 7am-5:30/6:00, Home at 6:00/6:30, family time until 7:30/8:00, work from 8pm-11pm(sometimes much later). Following this schedule was TOUGH and it, like training for anything, resulted in me being able to be disciplined about working. Will I now go soft since I won’t be working the same number of hours?
  2. No Single Inspiring/Driving Goal – Achieving my goal of leaving the day job had become an obsession and now my current goals are less tangible… will my business not have a stimulating goal and as a result be directionless?
  3. Playing Not to Lose – For those that play/watch sports we all have experienced/seen a team take the lead and then play not loose vs playing to win. Will I now play not to loose vs take bigger swings?

What Will I Do Now?

  1. Improve My Website Portfolio Management and scale select websites
  2. Be More Active With
  3. Expand Services to Include More “Higher Touch” offerings
  4. Grow
  5. Go to conferences and engage with the community more
  6. Now that I have my "cash flow" businesses moving I will look to take bigger swings with disruptor businesses (such as
  7. Spend more time on other neglected areas of my life…
    • Family (although not sacrificed much for my online business I now have more time to spend with them)
    • Health/Fitness/Outdoors – Definitely neglected over the last few years and looking forward to doing a lot more!
    • Ongoing Education – I have been on a very light information diet and am excited to tackle learning and applying new skills. There are many great courses I know I can learn a lot from!

The majority of my goals for the year will stay the same

If You Could Learn Only One Thing

From working with people I have found there are plenty of things people are a lot better at than I am but if there was one thing that I continually seem to be able to bring to a business it is this repeatable system…

My Process for Getting A Lot of Work Done Systematically:

1. Identify need/problem (me, project manager or one of my team leads)

2. Create a quick procedure for it (me, project manager or one of my team leads)

3. Assign it to a team member or hire 3-5 people on (project manager or team lead)

  • Give the 3-5 people a similar test assignment with no interview and minimal training (project manager or team lead)
  • Review quality of work done and communication and then fire all but the best (or fire all and repeat hiring a few more)

4. Assign the (potentially new) team member to execute the created procedure and work together to improve it (project manager or team lead)

5. Manage the change to the new procedure (project manager or team lead)

  • Input the new procedure into the procedure database (list in a google doc)
  • Communicate the new procedure and the basics of the change to the affected team members

6. Begin executing the procedure (new team member)

7. Improve & Track Desired Results of the New Procedure

  • a. New team member to send out weekly update with basic update to entire team including myself focusing on the metrics of both what has been done and how it has impacted the key end result the new procedure was put in place to improve (new team member)
  • Key metric(quantitative or qualitative) for the new procedure added to the team lead or project managers weekly business scorecard which gets reviewed at the weekly 1 on 1 meeting I have (most important 1hr I do all week)! (project manager and myself)

Executing this boring series of steps repeatedly over the last 8 years has built up a team with team leaders responsible for results and managing their team as they see fit (hiring/firing), weekly reports and a pool of great A players who I can leverage for any new project. Plus most of the processes in my business following a decent procedure.

If you are struggling to get your business setup with a team and systems I highly recommend you give the above 7 steps a try!

Thank You!

To everyone who has visited this website, emailed me, supported the business (even when you thought I was crazy – wife) been a customer of one of my services or responded to a question thank you!!!

If there is ever anything I can do to help you (visitor) achieve your goals with your online business please do let me know!

Finally Good Luck!

For those of you looking to make this same jump happen I hope that this post provides some insight into my mindset as I journeyed through my online business up to this point. If you can take anything away from this that increase the chances of you achieving what you are after or shortens the 8 year journey I took I would be very happy.

About the Author Jon

I am a 33 year old husband, father of 3, engineer and a huge fan of developing systems to build useful and profitable websites. The reason I build online businesses is to provide financial independence for my family and yours AND so I can spend time outside skiing and biking with my family.
Jon Gillham, Online Entrepreneur

Leave a Comment:

Kristy says June 15, 2016

Well done Jon, I have been following you for a long time and it is very motivating to see your success!

Loz James says June 15, 2016

Congratulations Jon – that’s great news!

I wish you the best of luck on your entrepreneurial journey 🙂



Tinh Nguyen says June 15, 2016

Fanstatic. I already set the finance target for my family too. Once I achieve it, I will quite the job and work fulltime with my favorite online marketing business. Congrats bro! Thanks for sharing and motivate me.

Ryan Nelson says June 15, 2016

Awesome to hear – when we had our call a couple weeks ago I had wanted to ask you your thoughts about staying with your full-time job while running your various online endeavors. How it was you could manage to balance both so effectively (obviously you outline your systems and processes on this site)- but it seemed like you had so much online success that it would be worth it to double-down your time on it. Congrats!

Jonathan John says June 15, 2016

CONGRATS, Jon! I’ve been following AWI for a couple years now and your journey is really quite inspirational. This is probably the only IM blog I’m subscribed to for email updates, which is saying something given how much I read online. 🙂

But anyways, congratulations on meeting your goals! I’m super-stoked for you and your family and can’t wait to see what else you’ll accomplish! Especially looking forward to more frequent AWI posts (maybe another epic guide soon? 😉 ).


Josh says June 15, 2016

Awesome article! Congratulations and all the above. I’ve followed you for years, and have similar goals. Its an inspiration to see you meet the ultimate goal.

lusekelo says June 15, 2016

Great,I a m going to quit my job too,i am planning to to it at the end of july,you´re the insipiration.

Brad says June 15, 2016

Congratz buddy! Happy for you man, you’ve worked hard and deserve it!

Gavin says June 15, 2016

Great write up and congrats Jon! I look forward to reading more about your successes and continually working with your team.

Lewis Ogden says June 15, 2016

Hey Jon, this is awesome news and I am so glad for you!

Like you said, you could have done this a lot sooner but you are an inspiration with your work ethic and ability to stick to goals and smash through them.

I can only see bright things ahead for you buddy and I wish you all the best.

– Lewis

Nicky says June 15, 2016

Superb to read Jon! Very inspiring- here’s the the next chapter- cheers

Curt says June 15, 2016

Jon man – congrats! This is amazing.

chuckie says June 15, 2016

Congrats jon, what a crazy journey!

Debbi Dybevik says June 15, 2016

Jon – I’m very inspired by your story!
I want to work for you! What project do you have that I can assist you with?

Charles Floate says June 15, 2016

Well done Jon, a very inspirational post.

High Supplies says June 15, 2016

Hi Jon,

If you get bored, you are welcome to boost my site anytime!

Venkatesh A says June 15, 2016

Hey! Jon This post makes me Quit Not the Blogging and motivates to keep going.

Thanks for sharing.


Venkatesh A

Dannielle says June 15, 2016

Congrats!!! You are extremely bold. If you did not believe in yourself you couldn’t have done it. I don’t think that you will go soft. I think that you will push yourself even harder knowing that you achieved so much on the schedule that you had. You’re an inspiration.

Nick LeRoy says June 15, 2016

Congrats Jon. You’ve come a long way to get to this point. Hopefully your new found time will allow you to continue investing your time and resources into many more business adventures. Out of curiosity, how much did having to pay for your own health benefits + family 100% impact your decision to go “online” full-time?

Chris Naish says June 15, 2016

Congratulations Jon, nice to see one of the good guys make it. Now take a vacation, you’ve earned it! 😉

Marc says June 15, 2016

Congratulations Jon their dedication and decision is an inspiration to all who aspire to online life.

Quinton Hamp says June 15, 2016

Dude. So much Epicness!

Your systems are something I covet. It’s time that I master systems.

I love the juxtaposition of “do the hard work” and “light information diet”. Most of your readers (myself included) are all about chasing the information and avoiding the work. You have the right formula. You may find that — aside from reading more books — you don’t do as much information consuming as you thought.

Finally, I love that you waited for a runway. I don’t think I would have ever gotten off the ground had I waited for that. My jump was essential to my success. But now I’m finding that my A)lack of runway and B) lack of income diversity has left me in a scary position.

I’d be curious to know how you came up with your runway figure. Was it a monthly multiple?

Congrats again.

Neale says June 15, 2016

Jon congrats on arriving at this first destination. I too have followed you for many years and am impressed in the way you treat this like a business, corporation would probably be a better word. Looking forward to seeing what you can do now you have all that time.

Raweewan M. says June 15, 2016

Finally the day is come. Good luck for your journey!

Ashraf Zaman says June 16, 2016

Carry on Mr. Jon. I am new in this field. I inspired from your history how you achieved your goal. I am following you from now.

Md Babu says June 16, 2016

You have inspired me again Jon 🙂 I want to send you an email, can I get your best email ?

William M. says June 16, 2016

Awesome man!! Great planning and execution! Looking forward to seeing your progress!

Chandler Smith says June 16, 2016

Good stuff man. I remember when I left my “day job”, which was actually just my own self-employed business, to go full-time internet marketer. I was much younger and the $8k a month I was pulling in was plenty. Unfortunately I got sued for what amounted to telling the truth about a product’s flaws – they initially claimed libel, then switch to trademark infringement because the photos of their product that I took had the product logo displayed. Seriously?! Anyway, what I’m getting at is, stay diversified and pad your income just in case something unforeseeable happens. Best of luck man!

Mahade Hasan says June 16, 2016

Congratulations & Thanks

Alex nob says June 16, 2016

Wish you big successes for the future guy, i’ve really learnt a lot from what you’ve been sharing. Thanks.

Owen says June 16, 2016

Congrats Jon.

Side note: Since you have more time now, you might want to check your auto-responder sequence for the 7 part process regarding your masterplan template. I’ve signed up with 3 emails just for that and none of them got the 7 part process, only the main template.

Shashank Gupta says June 16, 2016

Congratulations Jon and wish you all the best for the new beginning. I wish now your earning will further boost as now you are full time into it 🙂 Love reading your posts, they are very authentic and inspirational.

Ben says June 16, 2016

I think this is s move you won’t regret, look at what you’ve achieved so far and with your ability to add movement systems can only grow for you now your focus is 100% in the right place. Look forward to watching you fly

Matthew Allen says June 16, 2016

Again – congratulations Jon! I just know we’re going to be seeing ridiculous stuff from you in the future, now that you’ll be working online full time. Can’t wait to see exactly what that stuff will be.

It’s been an honor getting to know you throughout some of the middle years of your journey and it’s been fun watching your progress ever since.

Thanks for sharing all in this post too! Very motivational. In your 3 New Concerns section – point #2 really hit home for me. It made me realize that I’ve NEVER had a single driving/inspiring goal. I need to get one of those and post it publicly on my blog.

Cheers to continued success! Good Day!

Ivo says June 16, 2016

Congrats man! Been following you for a few years. Never had a doubt that you’d be highly successful in this. Also having a full time job, wife, and kids, I’m amazed by your work ethic. You seriously need to write a post (or book) on Time Management. I’m so close to making the move as well (income is good but not diversified enough in my case).

Bryn Lieb says June 16, 2016

Congratulations Jon!

Konrad Braun says June 16, 2016

A huge congrats for finally pulling the trigger. Very inspiring 🙂

Alistair Cochrane says June 17, 2016

Well done Jon ))

“Achieving my goal of leaving the day job had become an obsession and now my current goals are less tangible… will my business not have a stimulating goal and as a result be directionless?”

You are a successful guy. You worked hard and got your freedom. I’m surprised it took you so long to quit.

From the outside… maybe your challenge now is to make sure you don’t go on to be very successful in things that don’t really matter. You’re winning the game… in fact you’re kicking ass… but are you playing the right game? ))

So maybe your next big goal won’t be a business goal…

Congratulations again and keep up those audiobooks ))

Khandaker Monjurul Haque says June 17, 2016

You should good luck and i hope that you are more progress in your carrier. Next, i want to help from you to learn SEO.

Michal says June 17, 2016

Aww, Congratulations!
Now – my turn:)

Tim says June 19, 2016

Hi Jon, I’m so excited to see you take this step because it gives me hope that I can to! I’ve got a lot of the same why’s in my life. I’m grateful to know you and to have been able to talk with you about business opportunities. I can’t wait to see what’s next!

Naveen Kulkarni says June 20, 2016

Hi Jon,

Congrats and happy for you that you have finally taken that leap! One question Job, not sure if someone already asked or not.

Since you are doing this online business for eight years as part time, how it overlapped or interfered with your full-time job? I mean, whether there were any issues from your full-time company if they knew that you are doing something apart from working for them?

You can ignore this question if it sounds too personal 🙂

Dave Child says June 21, 2016

Congratulations! It’s a great step to take. I started working for myself four years ago and have loved it – I see so much more of my family, on my own terms, and with more job security than I ever had working for someone else. What’s not to like?

Yaro Park says June 23, 2016

Congrats Jon!
I was always surprised you didn’t quit yet and finally you made the move.
I quit my job right before new year and my online income was 50% of my goal, but i still think i didn’t right decision. After 6 months working for myself I doubled and even tripled income and I hope it will go up more.
Working for yourself much better for me, but there are cons of course. 🙂
I am excited to see how will be you progress in next 3-6 month compare when you were working part time on your business.
Good luck!


MegCor says June 28, 2016

You are the inspiration everyone one looks for. You set the goal, followed it religiously and proved that it can be done. Without making too much noise. I always thought when you will quit your day job, in fact last month I was going through an old post of yours when this thought struck my mind.
Today I saw your email and wow…

Congratulations, you deserve it.

rohit says June 30, 2016

Hello Jon, very Interesting story blogging needs time and you have spent time on it and results are here. great to read this article.

Tom says July 2, 2016

As an early retiree (retired age 27) I share many of the concerns you laid out.

1. Getting Mentally Soft – For people like us who always want to get better and smarter, getting mentally soft isn’t a problem. You touched on getting less chronologically disciplined, which is a serious threat though!
2. No Single Inspiring/Driving Goal – Yes, I really miss how driven I was when I was working toward retirement, saving over 80% of my take-home pay. In general I start to feel a lot less motivated whenever it’s been too long since the last complete redefinition of my reality. Stay hungry. Stay foolish. Challenge your beliefs.
3. Playing Not to Lose – I think this is more a result of success+fear, or of changing priorities toward security and away from growth, not so much a result of job vs entrepreneur lifestyle/income.

Another worry to add to this, and it could be made more or less intense by moving cities, is social life. Obviously make family top priority, but you may miss the forced social connection to people who are really skilled at their crafts that day-jobbery provides.

To combat this, do a sport or hobby, do stuff at a local university if possible, go to coffee shops or the library, and periodically read through the whole gigs/computer services section of craigslist or similar (I heard craigslist is called Kajiji in Canada). Contact the interesting posters and be open to meeting them, collaborating with them, referring customers to them, or serving them (if they’re potential customers). is also really useful for finding hobby groups or relevant meetups for freelancers, like SEO specialists for example.

I’m going to apply your advice for getting a lot of work done systematically. I haven’t done that yet, so it’s really valuable to learn that from you. Probably years of trial and error distilled in that 7 step process.

Zbynek says July 26, 2016

Hey Jon, congrats on this decision! Nice to see your path and I wish you all the best on the enterpreneur future. One thing which many startups forget is to maintain sustainable and reasonable big business – the goal is not to grow like cancer. Be the great company, not the biggest company 🙂

    Jon says July 26, 2016

    Hi Zbynek, great point… although some people do truly want to grow big for the sake of big and that is admirable… it has not been the focus of my business.

Juan Rademacher says February 20, 2017

Thank you Jon for sharing the timeline of your amazing journey to online financial independence. I especially liked your insight that there is no easy way to build and maintain an online business… that you have to be willing to do the hard work.
Thanks again,

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