How to Increase Your Odds in the Job Lottery

mm Russ Finkelstein

I love my parents and, as I’m sure you can tell from just looking at my profile picture in the by-line up there, they did a fantastic job raising me, and my siblings.

They also bought a lottery ticket once a week. When I was growing up, my parents talked often about how our lives would change when we had “won the lottery,” and yet I somehow knew even then that it was unlikely to ever happen. From a young age I had limited my flights of fancy.

It only dawned on me later that this was an indicator of what felt possible to them as they pondered a future that could be filled with plenty. The lottery seemed like the best possible option to get to the good life.

My parents sacrificed a great deal for the four of us, in every way, and set great examples. But now that I tend to spend so much time discussing careers, I’m often struck by how many of the people I’m coaching tend to take a “when I win the lottery” approach to having a job they like.

Call me revolutionary, but I think you deserve to have a job that fulfills your needs. A job you love, if a job you love is what you want. Many people think I’m bonkers to say so, but you really don’t need to be a martyr to achieve your career goals. It is often as simple as doing a few things to improve your odds.

Three out of four Americans are unhappy in their jobs, so the odds of having a job you like are in fact a little better than the one in 14 million it takes to win the lottery. But the truth is, many of us continue to suffer in careers that make us miserable, because instead of being willing to follow a few simple steps to get clarity about a next move, we simply chalk our unhappiness up to our lot in life, and shrug, saying, “when I win the career lottery, everything will be different.”

Then we go out for happy hour. Then we do something distracting on the weekend. Then we head on back into work on Monday morning hoping that tickets pays off this week. Even though we’re sure on some level that we deserve better. Don’t we? Tolerating work to enjoy life outside work is something that some seek, but for many it is not what they have chosen, but rather accepted.  

If you feel like this, I sympathize. You are by no means alone. In fact, we’re all struggling with a pretty odd attitude to work in this country. American culture, for example, is full of archetypes, men and women, unhappy in their jobs but who love their families, and sacrifice career satisfaction to pay for a semi-fulfilling life at home and the hope that their children might somehow have it better.

The truth is that we live in a time where downward mobility is becoming more of an expectation and therefore we owe it to ourselves all the more to locate work that resonates with us.

Like buying a lottery ticket, to escape, we often seek quick access to something that will improve our career malaise. Perhaps we scan the job ads looking for roles in a certain field in a certain city with certain compensation, and submit a form resume and a blah cover letter. What I know from serving in the recruiter role is that any job worth having will receive hundreds of applications all too easily, and unless you’ve made an effort to truly stand out, you’re wasting your time. Applicant Tracking Systems show that most jobs have 200 applicants, with 20 being reviewed, up to six being given a phone interview, and two to four interviewed in person. You might as well just buy a lottery ticket.

If you “won the lottery”, you’d have a job you wanted, with the income you wanted, in the city you wanted to be in, and all of your work problems would be solved.

Problem is most of the time winning the job lottery most often means accepting a job that you don’t know that you want. At least when you win the lottery you can do what you want with the money, minus the hefty tax on your prize.

Here’s the thing. It takes more time to dig down into the details of why you’re unhappy, and you need to believe in yourself a little bit, before you can really start to pull the threads on those issues, to figure out what might actually help you to find a job that you might enjoy more. Here are some things to shift from a lottery ticket buyers’ chance of finding a job you like:

  1. Know what you want: You need to prioritize your criteria. There are many different criteria you might prioritize as you consider what work you might pursue next, from prestige to a good boss to autonomy to flexibility to salary or a specific workplace culture, and so on. In most cases you can want, but can’t have all of them. It is unlikely that you can earn $150k a year working with developmentally disabled orphans. Honestly. So: What do you want the most? What comes right after that? Establish what’s the priority right now and use that to guide your choices?Knowing what you really want is the only way to get fulfilling work!
  2. Personalize what you create: Whether it’s job applications, your LinkedIn profile, your resume, or emails you’re sending to ask people for advice, it’s very important that your narrative, your elevator pitch, whom you are when you present yourself to people, is down pat. If you are applying for something, give them a very focused version of you that gets across why you are a serious applicant. If you’re going to people seeking help, know what are you looking for. What do you need from them? It is OK to say that you are gathering information if that is the stage you are in now. Just let them know that you realize that you are still in a place of exploration. Whether you know what you want OR you are exploring possibilities, you should have a set of questions to ask that you ask everyone. If you are exploring fields or roles, these questions help you get clear about possibilities. If you know what you want, these may be more about understanding employers, where to network and how to be the best candidate.Showing employers that you know what you want and that you applied because their position, correctly, fits what they are seeking, dramatically improves your chance of getting an offer!
  3. Reach out with direct requests to your network: You all have contacts. Fortunately, these contacts also have contacts. This World Wide Web is aptly named. This is the time to ask people for help, feedback, and advice, and for specific things, in the case of your search. I know that you last saw Aunt Wilma in person when she brought over the noodle casserole for your cousin’s Sweet Sixteen two years ago, and who would have known, she knows someone as Google! Funny thing is, she would love to make that intro because it gives her bragging rights at the next Thanksgiving meal. It also can make a huge difference when you apply that someone will vouch for you. I know that this feels like it takes more of your time.Having a contact at a company can improve your likelihood of getting an invitation to interview by 40%! Asking those you know to make introductions has an enormous impact on your getting an interview and a job offer!
  4. Move away from the keyboard: A recent CareerXroads survey showed that only 15 per cent of positions were filled through job boards. Many people spend the majority of their search time clicking on links to review and apply for jobs, often as though there is a clock ticking down, and the more you apply to, the more you win. Even if you find a job that intrigues you, it is incumbent upon you to see who in your network works there or knows someone who does. Refer back to the tip above. If you aren’t seeing much that intrigues you, please consider that 85% of jobs simply are not listed online. This means doing a lot of work in person, having coffees, meetings, letting your friends clearly know what you are seeking, and so on. So, by all means apply for things online, but you hurt yourself by stopping there. Compliment it with real, in-person commitment to activities where you’ll connect meaningfully with folks. Join a professional organization to get things moving.The job search can feel like a numbers game. We want to make it feel less like the lottery and more like something you have control over. Having a search that takes you away from job boards puts more opportunities in play and gives you actual connections to those jobs as you discover them. That’s the elusive “win-win”, in the world of the job seeker.

As a coach, the role I often play is to get people to believe in themselves and see the steps they can make to get the life that they want. Don’t leave your career happiness up to luck or happenstance, because the odds aren’t in your favor. You have the power to get much closer to a life and profession that’s going to make you happy.

Or you can continue the search on blind faith that it is going work out.  Which reminds me of one of my favorite jokes:

There was a preacher who fell in the ocean and he couldn’t swim. When a boat came by, the captain yelled, “Do you need help, sir?” The preacher calmly said: “No, God will save me.”

A little later, another boat came by and a fisherman asked, “Hey, do you need help?” The preacher replied again, “No God will save me.”

Eventually the preacher drowned & went to heaven. The preacher asked God, “Why didn’t you save me?” God replied, “Fool, I sent you two boats!”

I’m surely not God, but please consider this a boat.

Russ Finkelstein is Managing Director of ClearlyNext, a guided online career program that helps people of all backgrounds and incomes figure out what to do next. Read more >