How to punch self doubt in the face

I love the few weeks after the 1st of January. I like to think of it as the “brand new year” period.

It's full of hope and optimism and what could be.

What will you accomplish this year? What will you look back on and marvel at having done?

There will, however, come at time when you'll get frustrated. How things aren't going your way. Self doubt will start to creep in.

Maybe you have a savings goal and you're not saving as much as you want. Maybe you're working on a project and you thought you'd be further along. Maybe you see all the highlight reels on Facebook and wondering why your life doesn't measure up.

These thoughts get in your head and they get in the way of actual work. If you can keep your emotions in check, you can continue to do the work and make true progress.

Want to know a trick I use? I look back at the past.

I ask myself — Where was I ten years ago? Twenty years ago?

This trick works (for me) because daily, monthly, and yearly life is very bumpy. You win some, you lose some. We feel losses more painfully than gains, so it's easy to think we're falling behind.

Just thinking back and taking the long view to see overall progress is enough for me to get past any day to day frustration.

Let's see this in action… into the hot tub time machine!

20 Years Ago

Twenty years ago was the start of 1997.

That's me in high school, roughly 1997

I was 17. The age when you don't realize how lucky you are not to have any real responsibility but are so anxious to grow up.

  • I was in high school and working about 8-10 hours a week at a Chinese fast food place for minimum wage under the table.
  • I was saving a few bucks to a savings account.
  • I wasn't even sure where I'd be going to school yet because I was still a junior.
  • I was trying to do well on some AP classes so I didn't have to go to as many college classes.
  • … and things were great.

I was the typical high school junior and had very little idea of what I'd be doing in the next five, ten or even twenty years. My guess was that it would involve computers since they were all the rage but I was expecting it'd be in an office job of some kind. Probably a hot startup or two.

10 Years Ago

Fast forward ten years, which is ten years from today, to the start of 2007.

My lovely wife and myself in China

I was 27. The age where you're no longer a young kid trying to figure things out but not yet old enough to really be an adult.

  • I was working at Northrop Grumman, earning a respectable mid-five figure salary;
  • I was saving the maximum to my 401(k) and Roth IRAs;
  • I was about halfway through an MBA program at Johns Hopkins University, paid for by Northrop Grumman;
  • I was about a year or so into building my first business, a personal finance blog called Bargaineering;
  • I was dating the lovely woman who would later be my wife;
  • We owned a home;
  • … and things were great.


Aaaaand, fast forward to today.

Me and my lovely wife at a wedding last year

I'm 37. The age when you're finally feeling like an adult and trying to figure out how to not mess up your own kids!

  • I work for myself.
  • I save the maximum (that we can) to our solo-401(k);
  • I finished that MBA from Johns Hopkins;
  • I built and exited Bargaineering and now focus on this blog and $5 Meal Plan;
  • I am married to that same lovely woman and we have two awesome kids who test my patience every day;
  • We sold that first home and now live in our “forever” home;
  • … and things are still great.

No Bumps Along The Way?

What doesn't get said are the bumps along the way.

They are harder to remember over the span of 20 years (which is a good thing!) but here were some:

  • I entered the Intel Science Talent Search (what used to be the Westinghouse Science Talent Search and is now the Regeneron Science Talent Search) and did not get selected as a semifinalist. My public school senior year (Ward Melville High School) of 495 students has a special after school program for it called West Prep, lead by Mrs. Melanie Krieger. The New York Times even did a write up about our four finalists (the most in the nation) that year.
  • I applied to like 20 schools and was initially accepted to just two – Carnegie Mellon and SUNY Stony Brook (I grew up 15 minutes from SUNY Stony Brook). I would get into Columbia off the waitlist a month later.
  • I graduated college in December of 2001, a semester early, and into the worst job market for software engineers. (dot com bubble burst in March of 2001)
  • I started a one-year graduate program backwards, doing the Spring semester before the Fall semester, which put me behind my classmates — all of which had worked in industry. In one class, my group partners even complained to the professor about having to work with me!
  • I had the pleasure of experiencing both the dot-com bubble bursting in 2001 and the housing crash in 2008, all in the first 10 years of my adult life.
  • In every year I've worked for a company, I never got more than a 3% raise. Before you say 3% is great, I was in the defense industry and that entire time we've been in wars (Iraq, Afghanistan).
  • I've never been promoted. At any job. Ever.
  • When I left Northrop Grumman for another job, I was promised one role but slotted in another completely different one (though to be fair, the people I worked with were great).
  • Before Bargaineering, I started a website that never got traction and was shut down after a little over a year. (even the domain squatter that bought it years later let it expire!)
  • The first home we purchased lost $35,000 in value over 5 years and we put in about $15,000 of work. Ouch.

There were definitely more… but after 20 years they fade away despite how painful they may have felt at the time. I'm not going to lie, reading that list did bring up some feelings, especially the high school ones.

So to amend the original suggestion, when you do look back, don't try so hard trying to remember the low points. 🙂

Bumps Are Smooth at 30,000 ft

Seth Godin talks about the idea of a local max. Life is a series of local mins and maxes. If you rest on your laurels (local max), you won't reach your potential. If you get stuck in a trough of sorrow (local min), you can spiral out of control. Looking back smooths out the bumps.

There's a saying I really enjoy about raising children – “the days are long but the years are short.” The day to day stuff is exhausting but you look back at these little people and you realize how much time as flown by. You have, in essence, looked back 5 or 10 years. You remember when they were babies that only ate, pooped, slept and cried. Now they ride bikes, play basketball and do math too.

Over a longer period of time, the progress looks unbelievable. In a single day, you hope they take their afternoon nap.

It's also important not to constrain yourself to just looking at your financial or career achievements. There are fitness related things that I can do now that I wasn't able to do ten years ago. If career-wise and dollar-wise it feels stagnant, look to see what else you've been working on outside of those two very focused areas. You may be surprised.

Where were you ten years ago? What were you doing? How have things changed since?

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About Jim Wang

Jim Wang is a forty-something father of four who is a frequent contributor to Forbes and Vanguard's Blog. He has also been fortunate to have appeared in the New York Times, Baltimore Sun, Entrepreneur, and Marketplace Money.

Jim has a B.S. in Computer Science and Economics from Carnegie Mellon University, an M.S. in Information Technology - Software Engineering from Carnegie Mellon University, as well as a Masters in Business Administration from Johns Hopkins University. His approach to personal finance is that of an engineer, breaking down complex subjects into bite-sized easily understood concepts that you can use in your daily life.

One of his favorite tools (here's my treasure chest of tools,, everything I use) is Personal Capital, which enables him to manage his finances in just 15-minutes each month. They also offer financial planning, such as a Retirement Planning Tool that can tell you if you're on track to retire when you want. It's free.

He is also diversifying his investment portfolio by adding a little bit of real estate. But not rental homes, because he doesn't want a second job, it's diversified small investments in a few commercial properties and farms in Illinois, Louisiana, and California through AcreTrader.

Recently, he's invested in a few pieces of art on Masterworks too.

>> Read more articles by Jim

Opinions expressed here are the author's alone, not those of any bank or financial institution. This content has not been reviewed, approved or otherwise endorsed by any of these entities.

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  1. Rohit Malhotra says

    Great post. 10 years ago I was about to finish my MBA. Things have changed so much. I started as a stock broker but then built an online business and now run a publishing company and run a blog. I never got promoted in my job too! Maybe that’s a good thing.

    Rohit I Lifeselfmastery

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