Give Me Back My Five Bucks

Guest Post: The Road to Success is Paved with Luck

NOTE: I’m in Seattle today, so today’s guest post is by Robb Engen, who writes about personal finance at Boomer & Echo.

I like to think I’m a fairly successful person. I have a beautiful wife and daughter and a fulfilling career. I live in a nice house, spend less than I earn, and have managed to put away some money for a rainy day. Things have turned out pretty good for me so far.

Yet when I’m asked how I got to where I am today, I struggle to come up with an answer. I wish I could say this was all part of a well thought out plan, built on years of hard work and sacrifice. But the truth is there were a lot of lucky breaks along the way.

For ten years I worked in the hotel industry and I literally started at the bottom of the totem pole, carrying bags and running errands for hotel guests. Because of the nature of the industry, there’s a lot of turnover each year, so just by sticking around for 2-3 years I was able to work my way up to a supervisor role at the front desk.

When my manager left, I thought I would apply for that job. I was finishing up school and ready for my first crack at a leadership role.  Unfortunately, I had a terrible interview and clearly wasn’t ready for that position. Thankfully the General Manager saw some potential in me and asked me to transfer to a supervisor position in the food & beverage division. There I would get a broader range of experience in the industry, which would prepare me for the next step.

I wasn’t cut out for food & beverage and after 9 months I was ready to give up, but I caught my first lucky break. One of the sales managers at the hotel was going on maternity leave and recommended me for her replacement. This time I was ready for the interview, but I still had very limited experience and thought I wouldn’t stand a chance. Somehow I got the job, and I was so excited to get hired that I jumped at the low salary they offered me. Oh well, my foot was in the door.

Nearly a year went by and I was excelling in this role, but I still didn’t have any job security. The next lucky break hit me about 10 months into this job when my boss quit to start her own business. The sales manager returned from maternity leave to take the Director role and I was hired on as a full time sales manager.

Another year went by and I was doing a really good job hitting my sales targets and developing some leadership skills. I was ready for more, but this time there was nowhere else to go. My boss would have to leave, or I needed to go. Amazingly, right at my breaking point, my boss left for another opportunity and I was promoted to Director of Sales.

At 25 I had reached a position that was typically filled by 40-something’s with 20+ years of industry experience. Yes I worked hard and was good at my job but, without those three lucky events, I would have surely ended up on another path.

I talk to a lot of young people who are looking for the secret to a successful career. They ask; how do I get to where you are? I wish there was an easy answer, but there is no blueprint for success. My advice to them is put yourself in the right situation to succeed. Rather than jumping from job to job, stick around and make your own luck by being in the right place at the right time.

Robb Engen lives in Lethbridge, AB and writes about Canadian personal finance at Boomer & Echo. Together with his mom, (she’s the Boomer, he’s the Echo) they offer their own unique perspectives on saving, investing and personal finance.  You can follow him on Twitter @BoomerandEcho

Author: Krystal Yee

I’m a personal finance blogger and marketing professional based in Vancouver. I’m a former Toronto Star (Moneyville) columnist, author of The Beginner’s Guide to Saving and Investing, and co-founder of the Canadian Personal Finance Conference. When I’m not working, you can usually find me running, climbing, playing field hockey, or plotting my next adventure.


  1. Jeff says:


    I think your story illustrates the importance of working hard and developing strong relationships within the workplace. 4 of the 5 jobs I’ve had since graduating university have come through references / networking. By representing myself professionally, generally doing good work and showing ambition, I’ve created my own luck in a sense. In one case a former boss landed a senior role and they essentially created a position for me to join them.

    I think it’s really important to communicate your goals within the workplace as well; let your managers and senior staff know you’re coming to work each day with a purpose – not just to bide time / collect a paycheck.

    I think there is creedence in sticking around a workplace – but for some careers, mobility is a good thing because it exposes you to different working environments and different ways of doing things. In your case, changing divisions was akin to that, I think.

    • Echo says:

      It’s true, networking (and general likeability, for that matter) plays a large part in getting exposure to other opportunities.

      Still, when I left the hotel industry for my current job, I was just meeting with a client for lunch to go over a sponsorship deal and she mentioned that she was restructuring her office and looking for a business development manager. I ended up getting that job, but the timing of our meeting and conversation was very lucky.

      I like your comment about creating your own luck and communicating your goals. Thanks for sharing!

  2. It is often said that we make our own luck. While there are many events beyond your control – such as when other staff take their maternity leave (OK, I suppose you could influence that, but this is a family-friendly comment) – there are some things you do control:

    Being ready to take advantages of opportunities.

    Keeping a watchful eye, so you can pounce on opportunities.

    Self-improvement, such as education, character improvements, etc.

    In other words, you could just as easily have reworded your sentence… “Yes, there were three lucky events, but if I hadn’t I worked hard and and been good at my job, I would have surely ended up on another path.”

  3. After reading this post, I wondered “is it really luck that got you where it did?” To me, it looks mostly like hard work along with a few breaks to help it along.

    I’m always hesitant to use the word “luck” when it comes down to something that you take action on and have control over. To me, luck is more like winning the lottery or something else that’s more or less random or unpredictable. To me, your story is more about putting yourself in a situation to succeed, as you said at the end of the post, and I think that’s worth a lot more.

  4. Echo says:

    Hmm, maybe “patience” would have been a better word than luck. I can’t help but wonder where I would be now if it weren’t for those three events. If I were the impatient type, I would have ended up jumping around in a series of lateral career moves while searching for the right path. I’ve seen it plenty of times over the years.

  5. I don’t think you’re giving yourself enough credit. Sounds less like luck and more like working hard and putting yourself in the position to take advantage of opportunities that came your way.

  6. Shannon says:

    I really liked reading this post, I work in the restauarant industry and have for 4 years now. It’s not the line of work I am aiming for as a career, but when I started as a 16 year old female who had never even cooked Kraft Dinner, I never thought how much I would be able to learn. It’s true that in the food and hospitality industry there’s always new opportunities.

    • Echo says:

      Shannon, it’s true – there’s a lot of turnover in the hospitality industry which leads to some great opportunities. It’s a tough industry though, definitely not right for everyone.

  7. Thanks for this post! I’m a firm believer that luck/circumstances plays a big role in our lives. I was lucky to grow up with middle class parents who were able to help me start off on the right foot. Working with people whose parents abused them or started giving the drugs at 12 (did you know thats the 12 is the average age kids start using drugs. The average. wtf) I can see how circumstances affected all of their future opportunities. When people who have had lots of privilege and luck believe all of their opportunities were solely a result of working hard, it really discredits people work really really hard but don’t always have as much to show for it.

  8. Mikhaila says:

    I feel like sometimes the only reason I’m in the job I’m in is because of luck – a friend of mine couldn’t take a temp position so I went instead, and that temp job led to a six month temp gig, and then to a permanent position. I was lucky initially, and then I was lucky again when the woman who was on mat leave decided not to come back.

    That being said, it’s your hard work and dedication that put you in the right place at the right time for those positions, so kudos!

  9. jay says:

    I think there’s a lot of luck, and I’m really grateful for it. I mean, really… being born into relative privilege (by which I mean, Canada!)

    That being said, I do try to reduce the influence of the unknown in my life. And there’s also such a thing as bad luck and it’s important to prepare for when it hits.

  10. Nice post Robb.

    Hard work and luck have a strong correlation.

    Sprinkle in a little bit of patience and taking some risks now and again, and you’ve got success.

    Kudos to you for working hard, being patient and taking some chances when they arose. ;)

  11. Sandy says:

    There is no doubt that hard work played a big role in your successes, but it is definitely true that you also had some luck on your side. There are plenty of people who are born on third base but think they hit a triple, so it is extremely refreshing to read a such a humble and honest post. (You, my friend, have gained another reader)

    I agree with @changeonabudget that “When people who have had lots of privilege and luck believe all of their opportunities were solely a result of working hard, it really discredits people work really really hard but don’t always have as much to show for it.” There is so much luck involved to achieving a success including things like being born to a good and stable family, avoiding catastrophes, avoiding childhood homelessness or abuse, having good health, etc.

    There are so many factors that can affect the trajectory of a person’s life…factors that people who have never experienced true hardship fail to think about.

    But of course, working hard to take advantage of one’s luck like you did is worth commending! Thank you again for your guest post!

  12. Tony Scott says:

    I agree with you and with Jeff. Luck may play a great part in our success but it must be accompanied by hard work and good relationship with fellow workers. We may have the qualities of a good manager but if we are not liked by those who would be making the endorsement and decision,nothing will happen. Just like if there’ll be no opening at that precise moment for you to rise and be acknowledged, which could be considered tough luck!

  13. Hey Robb! Lookin’ good!

    And nice post :)

    It was really nice reading your background story. Sounds like you showed determination and hard work, and not just ‘luck’.

    Funny, BF and I were talking about his career path (over Pho, of course). He was saying that his 3rd employer (he’s on number 5 right now, yes) was the one that gave him the lucky break. He was able to move from a role of general logistics to a specialized position in purchasing. Because of this, he was able to a) become specialized and b) make much more money than before, had he stuck to his previous role.

    • Echo says:

      @youngandthrifty – Hey, why didn’t you didn’t have to submit a picture for your guest post here? ;)

      Thanks for your comment! It was one of my bosses who mentored me and taught me the actual hotel business and how to make a career out of it. Definitely helped lead me down the right path, and even though I’m no longer in that industry I am still grateful for the opportunities it provided for me.

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