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Jonathan Milligan had no idea he’d be doing what he’s doing today. He tells his son to keep his eyes open because this generation will create the jobs and opportunities that didn’t even exist as options when Jonathan was in school.

Both of Jonathan’s parents were teachers, so being in the environment, teaching was a part of him as well. After college, he also started out as a High School teacher and coach but only stayed in that position for three years. He loved teaching but the context was wrong for him-it was too structured for his entrepreneurial spirit.   He took time off to ‘figure it out’, getting a night job in a call center for nine months. He read all there was on starting your own venture but didn’t put anything into action. Finally, he felt that he was ready to go fail at something, because even failure was progress compared with being paralyzed from inaction.

His first round as an entrepreneur found him ‘flipping’ a house. Although he made a decent profit, he realized that was not his calling. Then, he took a 100% commission job recruiting for an executive search firm. He did that for 8 years and was successful, but he still had that entrepreneurial drive and wanted to use his gifts.

He then started blogging about the job search advice and strategies he had gained. He fell back in love with teaching but on terms that he could control.   The sky was the limit on income and creative freedom. He fell in love with it and he fell back in love with writing, a skill he hadn’t used very much since college.

When he started to see that people were getting value out of his blogging, it made him want to do it more and more. The next step was realizing that if they loved his free content, then maybe he could create something people would pay for.

From there, he progressed to what he’s doing today-he’s an author, a blogger, a speaker, and the host of 2 podcasts, Simple Life Habits and Blogging Your Passion.

Most Influential Mentor:

  • One of his mentors along the way was another blogger
  • He was always challenging Jonathan to stay with the things that are your ‘no-end path’, those certain things that you’ll never grow weary of learning about and being a leading learner for others.
  • He also said there’s only 2 things you can take with you to the grave in online business-your reputation and your email list. He was challenging him to build his email list because no matter ‘where you go’ online, you can take your followers with you

Challenges and Setbacks

  • There have been many opportunities along the way that felt like they were going to be the ‘big success’. That wasn’t really the case-it was always a little bit of learning and a little bit of progress each time.
  • One of the first things he started earning money on was Google AdSense. He got ‘Shiny Object Syndrome’ and tried to build oodles of niche sites on subjects he knew nothing about so that he could multiply AdSense income
  • He got to a place where he wasn’t enjoying any of it and was not inspired by any of the niche subjects. They weren’t benefitting anyone
  • He sold the additional sites and used the revenue to buy his first site, ‘Blogging Your Passion’
  • In retrospect, it was a very good decision because a year later, Google changed their algorithms and AdSense income plummeted for everyone across the board

Primary Drive

  • At heart, he is a teacher who wants to serve other people and now he gets to do that on his own terms
  • Having impact on others’ positive transformations is more rewarding than anything else he could do

Who He Helps

  • With his first blog, which originally focused on career coaching and has since morphed into coaching for self-development and productivity, he helps people discover what their gift is
  • His second blog, ‘Blogging Your Passion’, helps people identify the areas they’re skilled in and how to serve others doing that, by guiding them in creating their online businesses and content

Common Challenges he Sees

  • Almost everyone deals with mindset roadblocks. So many people find the idea of entrepreneurship challenging and it goes back to their identity.
  • They feel that they need permission to go ‘all in’ and they are fearful of failing. If you can unleash these roadblocks, it’s amazing what can happen in just 90 days.
  • If you look at someone that’s been successful in what you want to do, if you stripped away all their traffic and resources, they would get to success twice as fast. It’s not because they’re smarter; it’s because they’re not afraid to hold back

The 5 Essential Mindsets

  • In his book, ‘The 15 Success Traits of ProBloggers’, Jonathan spells out the 5 essential mindsets you need to have for success: passion, resilience, confidence, patience and consistency
  • Resilience is about having the attitude that everything is solvable. We always look at someone’s ‘front stage appearance’ and judge that to our backstage. We see the peripheral that makes it appear that they have their act together. In the back they’re also running through difficulties and challenges as everyone else

The 4 Core Habits:

  • Create-no matter what niche you are in, you need to be creating valuable content so that you can build trust with readers and viewers
  • Capture-keep building your email list and keep communicating with them
  • Compile-package your knowledge and expertise into products and services. Put something together so you can be officially ‘open’ for business
  • Connect-get out there, network with other people, build relationships
  • 90-95% of Jonathan’s calendar week is spent in one of those 4 areas

Advice on Being ‘All-In’:

  • The good thing about trying something is that you’re guaranteed to get a result. The only way you won’t get a result is to do nothing.
  • If you feel stuck right now, clarity is probably not going to come from you thinking more. You need to get out and do something. Even if you fail.
  • Trust and Authority are the ultimate gifts you can gain from a lifetime of serving others.

Favorite Quote:

  • “‘Clarity comes from movement” (Marie Forleo)

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