Time To Go Back To Work Full-Time Again? Benefits Of Getting A Job

Google bike at Googleplex

Updated for 2021. The real estate market, stock market, and private equity market are all softening. Going back to work to take a break from fatherhood after two year and making extra income sounds like a good idea now!

I recently visited my old friend Chris who works at Google. We first met on Craigslist when I put out an ad to hire someone to help build my blog network website back in 2009.

Chris took me on a two hour bike tour at what literally felt like a college campus with over 60 buildings. There’s all you can eat food from every type of cuisine. There are tennis courts, a soccer field, a wave pool, and freshly squeezed orange juice when you’re thirsty. Massages by appointment, daycare, and dry cleaning are all at your disposal. You basically never need to leave the Googleplex, which is exactly what management wants.

My time at Google reminded me about how much fun work could be.


After 16 years post college, I’ve been fortunate to experience working at a couple reputable firms full-time and pursue a dream of doing something entrepreneurial full-time as well. But several things besides my visit to Google have been pushing me to take full-time work seriously again.

  • No matter how much you love someone, it’s rather difficult spending 24/7 with your significant other every day, especially after at least one of you was out of the house for 12+ hours a day. Separation is very healthy for relationships. It allows you to recharge and re-appreciate what you have. I can’t go to the park every day at 11am to go play tennis with my fellow tennis bums either. There needs to be a change of pace.
  • Despite going through a couple downturns in my career, I never really felt that much pain because I was never laid off. The bi-weekly paychecks kept coming in during the dotcom bust and the housing market collapse. Sure, my year-end bonuses got slaughtered, but my lifestyle didn’t really change much because I always just invested all of my bonus anyway. As an entrepreneur, I’m hypersensitive to income fluctuations. Revenue can easily decline by 25% month over month as it recently did. There are so many exogenous variables that are outside of my control. If doom is around the corner, it would be nice to have some stability.
  • There’s no more fear of regret. One of the main reasons why I left my day job in 2012 was because I didn’t want to look back as an old man, filled with regret having never tried creating something on my own. A good 3.5 years have past surviving on my own and I’m proud of what I’ve accomplished. It’s hard to build a livable income stream that can support four people in San Francisco. Now that the challenge is complete, I long for a new challenge.

The combination of consulting and working on your own business is pretty fantastic. You can make a healthy income while having a lot of freedom. However, there’s a wanderlust feeling that grows when you don’t feel you belong anywhere. I think we all naturally want to be part of some type of organization.


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Before making a big decision, I like to write out my thoughts. Here are some of the things I miss about working full-time from my old shop.

  1. The camaraderie of working towards a common mission. I love working together on a good team that is looking to compete against another company. It feels exactly like playing together on a softball, basketball, or football team. As an avid league tennis player, I love coming up with the lineups and talking strategy with my fellow teammates. Sitting out a match to make way for a better player is not a problem because the thrill of victory trumps everything else.
  2. The corporate card. As a frugal person who likes to hustle, it’s awesome to be able to eat a free meal while developing client relationships. Because I love saving money, I made it a point to try and take as many clients out for lunch, dinner, and drinks as possible. The real reward was building one of the strongest west coast franchises on the street, which led to even more gains.
  3. The commiseration. Every day can’t be a good day. Sometimes we lose out on a deal, fall in the rankings, or get fired by a client. Commiserating with colleagues about what could have been always felt pretty good because we were in it together.
  4. The boondoggles. Every decent company spends a lot of time and money on making sure their company culture is strong. Part of good company culture is having happy employees who get along with one another. I know Uber, for example, had a company-wide trip (5,000+ employees) to Vegas for four days. Talk about fun!
  5. The security. Getting a paycheck every two weeks felt amazing. It was easy to save one and spend the other to get to a 50% after-tax savings rate. I’m now purposefully paying myself in the middle of the month to replicate a bi-weekly paycheck cadence because I receive my rent checks at the beginning of the month. Unless you really screw up, it’s hard to get fired.
  6. The benefits. I pay ~$1,460 a month for health insurance for two healthy people in their mid-30s. That’s a ridiculous amount of money when it costs a tenth of that amount in some other developed countries. I miss the 401k match and annual company profit sharing, although most startups don’t match. I also miss the continuing education training and tuition reimbursement program that paid for almost all of my Berkeley MBA. The short-term and long-term disability leave was also nice. Read your employee handbook everyone.
  7. The recognition. The most exciting time at the company was during promotion period. Everybody would eagerly wait to see who got on the CEO’s promotion blast list. The flood of congratulation e-mails, pats on your back, and handshakes if you got promoted always felt really good. Getting recognized for a job well done is a fundamental necessity.
  8. The networking. Even though competition was fierce, it was always fun to go to networking events and mingle with competitors. Some would share secrets about shared clients. While others might want to poach you away for big bucks. As a relatively extroverted person, the networking events were always enjoyable.


If you can find a reputable job that gives you the opportunity for growth, while giving you the freedom to pursue other passions outside of work, I dare say it could be an ideal situation. The trouble is finding that perfect company!

There’s nothing better than starting your own website to own your brand online and earn extra income on the side. Why should LinkedIn, FB, and Twitter pop up when someone Google’s your name? With your own website you can connect with potentially millions of people online, sell a product, sell some else’s product, make passive income and find a lot of new consulting and FT work opportunities. Start your own WordPress website with Bluehost today. You never know where the journey will take you!

Recommendation For Leaving A Job

If you want to leave a job you no longer enjoy, I negotiating a severance instead of quitting. If you negotiate a severance like I did back in 2012, you not only get a severance check, but potentially subsidized healthcare, deferred compensation, and worker training.

When you get laid off, you’re also eligible for up to roughly 27 weeks of unemployment benefits. Having a financial runway is huge during your transition period.

Conversely, if you quit your job you get nothing. Check out the book How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye.

It’s the only book that teaches you how to negotiate a severance. It was recently updated and expanded thanks to tremendous reader feedback and successful case studies.

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Updated for 2021 and beyond.

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