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. πŸ™‚

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. Brian @ Debt Discipline says

    Great reminder Jim. We often forget where we have come from. Ten years ago I was playing zone defense with three children under 10 years old. Now all teenagers and two are getting ready for college. I’m in a much better job and my wife and I have a plan for our money. All great progress.

  2. David G says

    What a great strategy. I think I have an obsession with local mins. The maxes are better. My student loan was 112k on August 1st last year. As of January 11, it’s 69.7k and falling. I still look at that and think…sixty-nine THOUSAND dollars??? OMG OMG OMG I’m going to die, this is horrible. I’ll NEVER pay it off. EVER!

    But, using the local max, I can breathe. The balance on August 1st was worse. Much, much worse. Strangely enough, I didn’t feel as bad about that then as I do about today’s balance today. Time to re-write the self-talk script, which means this post was right on time.

    • Jim Wang says

      Yes! This is exactly it — when you look at that balance right now, knowing nothing else, it’s easy to freak out. But look back just five months and it’s $42,300 higher (which, by the way, is amazing). $42,300 in 4-5 months is astounding.

      I wonder why you didn’t feel bad — was it such a large number that it didn’t feel attainable? I don’t feel bad that I’m not going to be an professional baseball player… but I don’t like losing our recreational softball games. πŸ™‚

      • David G says

        You are right, Jim. I had had that debt with my mid twenties, and I’m now 51. I had grown numb to it, it was there but something to be ignored, as I would never be able to pay it off.

        Then I managed to land a good job, I moved away from my wife to take it, lived in my car for months on end, and have worked 70 to 80 hour weeks at a job that leaves me hating life. I decided to attack that loan with everything I had, and I started in August.

        Now that the balance is a living, breathing thing to me, it’s like a growth that must be excised….compound interest keeps it growing like a tumor, and I’m just hacking away at it to the point that I can take a two week take home check of 4500 bucks and have 400 to live on by the time I go to bed that night.

        I think by the time I pay it off, my cerebral cortex is going to give out like a balloon blown up and then let go. My head will just fly around the room hissing from the air escaping, and then hit the floor. But I will be out of debt.

  3. Marisa Stone says

    Some days you need more inspiration than others. 10 years ago I was living in Hawaii(I know poor me). Single mom 2 kids, housing market crashed(wanna guess which industry I worked in). Struggling to make ends meet, in fact had a second job(was thankful for that).

    Wow…my life has changed in 10 years. Married to ‘my handsome prince’. Now 4 kids, one adopted, 1 birthed, homeowner, house flipper.

    This article definitely gave me a pause for reflection!

    Here’s to an awesome 2017!

    • Jim Wang says

      Yeah, it’s called an emotional rollercoaster for a reason right?

      Thanks for sharing your 10 year look back — amazing huh?

  4. april says

    What a great way of looking at things. 10 years ago I was attending community college courses in my hometown, trying to figure out what to do with my life! Now, at 29, there is still a long way to go, but I have also come a long way from that kid going to community college. Thanks for the reminder!

  5. Syed says

    Love the comment about comparing ourselves to others Facebook news feeds. It’s like comparing out blooper reel to someone else’s highlight reel! Not much good can come from it. This was a great exercise Jim thanks for the idea. It’s nice to see how far I’ve come from my first job as a starbucks barista back in high school.

    • Jim Wang says

      Yes, nothing good can come of it and it’s an exaggerated version of “keeping up with the Joneses” because now you’re keeping up with the best of the best Joneses. πŸ™‚

  6. David Weinand says

    Great stuff. After having left my job of 10 years last fall following a mess of a merger and in the process of trying to get my own company going – I often have moments of great uncertainty that I’m doing the right thing to support my family. But reflecting back on a really crappy 2016, I have to remind myself that I’m fortunate enough to have the resources to try to start this thing….. And 10 years ago, I had just left another job (after another bad merger) and things were bleak. I’m better off now!

  7. Super Money Woman says

    Great way to look at life. 10 years ago I was a free faced brand new teacher. And now I’m leaving the profession for pastures new.

  8. Leo T. Ly @ says

    Ten years ago, I was just starting my career and just starting to shop for a house with my girlfriend and didn’t know much about personal finance. Now, I am married with two kids, became a personal finance blogger and loves to learn new money saving ideas and sharing them too. I gotta say that these are two very different lives.

  9. 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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