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A Price Worth Paying: Investing in Myself

One of the scariest investment decisions I ever made was to invest in myself. 

When I was 18 and considered the decision to go to university, I invested in myself by taking on student loans.  At the time however, that didn’t feel like much of an investment or even a decision.  It felt like an obligation to follow the traditional path to success.

No one ever frames the decision to take on student loans as an investment decision.  It’s made to feel more like a necessity.  Perhaps if it was portrayed as an investment, students would think differently about their school choices and once at university, they would behave quite differently.

Instead, that decision is presented to us as a loan in order to unlock a stage of life that since the 90’s has been almost mandatory if you wanted to have any chance of succeeding in life.

The student loan decision was pretty much mandatory if you needed the extra money to attend the best school you could get into.

So that doesn’t really count as an investment decision in my opinion.

When did I really start to intentionally invest in myself?

For me, the first time I thought about investing in myself was when I considered quitting my first corporate job in 2008.  Even then, I thought about it as betting on myself and less so investing in myself.  Tomato, tomatoe I suppose.

Up until then, I expected my company to invest in my professional development by paying for me to attend conferences and workshops.  I figured it was their responsibility to do that, not mine.

When I finally made the decision to quit my corporate career, I cashed in my 401k (i.e. pension) in order to create some financial runway to figure out my next steps. 

I think that was the first time I slightly considered a decision as ‘investing in myself’ because I was literally pulling the money out of the stock market and reinvesting it into Roger Osorio, Inc.  This was a new startup that was still figuring out what it offered to the market.  It was pre-revenue, pre-product, pre-idea, and only guided by a fuzzy vision of a north star, but a guiding light nonetheless. 

Up until then, the stock market was what I thought about when I heard the word investing.  I figured, individuals invest in stocks and bonds and if you do it right, you make a return.  More risk, more reward.  But it wasn’t until much later in life that I realized how risky it really was.  I was betting on a team of humans that I didn’t know at all.  I was betting that they would behave properly, legally, and in the best interest of investors.  I was betting that they would not get caught up in scandals or criminal activity. 

Even the biggest or best companies cannot totally rule out the possibility of bad actors.  And yet, I invested in them as if they were the investment I could count on the most.  And yes, if you diversify enough, you can count on a certain amount of return over decades.  In any case, this was all I knew or considered when I heard the word investment.  A distant second was real estate and having grown up not really knowing too many homeowners, let alone any real estate investors, that didn’t seem like an option to me. 

So when I decided to take money out of the stock market and put it into my bank account (which, unknowingly, was one of the first steps towards investing in myself), that felt very different and made me think carefully about how much I drew on those funds.  I took on side-hustles and part-time jobs to create more cash flow so that I wouldn’t have to draw on those funds.  I suppose I saw it as less of an investment and more of a safety net.  In essence, I was afraid to touch that money or maybe I was afraid to take the leap and really invest in myself.

Several months later, I decided to go back to school and I took on more loans.  Once again, this felt like a normal and necessary decision to get the education I needed to launch the first phase of my reinvention.

The Moment I Started To Think About It as an Investment

After I graduated with my masters in psychology in 2011, I had the opportunity to travel to San Francisco with some friends to attend meetings with the network I was building over there through social media.  I saw this as more of an investment because it was not obligatory.  It was something I could decide not to do and there wouldn’t be any consequences, at least none I would ever know of.  At that point in time, the funding was primarily coming from credit cards.

I kept my costs as low as possible, staying with friends, flying discounted airlines, etc.  Ultimately, however, there was no financial return from this trip.  On the other hand, I made some interesting connections, one of which became a dear mentor.  That I cannot put a price on.  In fact, one of my interactions with him on that trip made it into my first book.

Nevertheless, this was the first time I felt I invested in an activity that was not obligatory and would only be for the purposes of creating new opportunities.

Was Working for Free the same as Investing in Myself?

In 2014, I had the opportunity to become a facilitator for Techstars Startup Weekend, a 3-day entrepreneurship bootcamp that is hosted around the world.  Event organizers would pay my travel but my facilitation services would be on a volunteer basis.  In addition to this event, I also agreed to speak for free at other events for the opportunity to practice my speaking and get experience.

Often, when I explained this to friends or family, I’d get the response, “so you’re working for free?  That doesn’t make any sense.”  Don’t get me wrong, I wasn’t excited about the idea of working for free, however, I also appreciated the early opportunities to grow and develop my speaking ability.  In my mind, this was an investment I was making in myself to get better at my chosen craft. 

Eventually, I started getting paid for speaking engagements, however, those early years were difficult.

Was Hiring my First Coach the same as Investing in Myself?

Then in 2015, it happened.  After years of being on my journey to reinvention, I knew that if I had a coach by my side, I could move faster.  Afterall, I had a masters in psychology focused on executive coaching.  I knew very well how valuable this was, however, up until then I told myself I couldn’t afford it. 

Finally, in 2015, I felt like I could NOT afford to be without a coach.  I wanted to make massive progress on my journey.  I felt there was so much more I could achieve with a coach by my side. 

I contacted a coaching company, set up a discovery call, and was presented a few packages.  Normally, the invoice for a year was almost $7,000.  Immediately, I thought there was no way I could do this.  I said I will need to think about this and that I’d get back to them.  I definitely had sticker price shock!  I had never spent that much on myself outside of university.  No vacation I ever took cost that much.  My car cost more than that, but it was paid off across 6 years.  This price got my attention and challenged me to think, “Am I worth this much?  Are my growth and development worth this much?”

This was the first time I considered something an actual investment in myself.  I thought to myself, “if I’m going to do this, it HAS TO pay back many times over.”

Now the only question left was, “Can I really make this pay back many times over?”

In the end, I decided that I would make it happen one way or another and I went for it: I invested in myself. 

About 6 months later, thanks to the help of my coach, I was able to create my dream role at a Fortune 50 company for nearly 3 times my salary when I started my coaching engagement.

I finally understood what it meant to invest in myself.  To bet on me the way I used to bet on stocks.  And when you bet on yourself, it’s truly the only bet that you have control over.  I can’t predict or control how an executive will behave, even at a super successful company.  What if he cheats, steals, or gets caught in some scandal?  I don’t know that person and I’m betting on them with my hard-earned money without question.  This time I was going to invest in Roger Osorio, Inc.!

Other Investments in Myself

Ever since I made that decision to invest in my coaching, I have invested in myself many more times.  I continued to renew my coaching contracts and have invested in myself in other ways:

• Attended Tony Robbin’s Business Mastery Event ($10,000 ticket + $2,000 travel)
• Online Courses and Masterminds (well over $20,000 to-date)
• Travel to Conferences + Admission (well over $20,000 to-date)

Not to mention, investing my time into experiences and opportunities that help me continue to grow and develop. 

Are you hesitating to invest in yourself? 

What was the last opportunity you turned down to invest in yourself?  What do you currently invest in?  How much better are the returns on those investments compared to the opportunity to invest in yourself?

It only takes one significant investment in yourself to help you shift your mindset about this.  I used to think it was my employer’s responsibility to invest in my professional development.  I suppose it still is, however, this time, I am the employer and employee! 

However, once your mindset shifts on this, you’ll never go back.  That’s what was so incredible about having that first breakthrough moment when I invested in my first coaching contract. 

It’s crazy to think how we won’t hesitate to buy ourselves expensive cars, vacations, meals, gifts, etc.  And the moment it comes time to invest in our growth and development, we freeze and think very carefully about it.  I get it though, because that was me.

If you need help shifting your mindset on this, I’m here to support you.  DM me on Linkedin, Instagram, or Facebook.  Reach out via my website. 

Investing in yourself is the price worth paying because of the lifelong benefits when it comes to personal growth, self-confidence, career, fulfillment and satisfaction and your overall quality of life. Just like I invested in myself, you too have everything within you to get a massive return on an investment in yourself, you just need to believe in yourself, resolve to make it so, and get started!