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Dear Shannon

Dear Shannon: Why does finding my dream job seem so tough?

Finding your dream job in sustainability can seem as tough as finding that perfect someone. Guess what: The search approach should be kind of similar.

If you have a question for Shannon, send it to

Dear Shannon,

I have been on the hunt for a new job in the impact sector for a few months and am getting nowhere. Searching for job postings through traditional channels it just not working for me. I put feelers out in every direction and am open to many types of roles but perhaps I’ve cast too wide a net. Sometimes I don’t get any response to my applications and other times I think things are moving forward and then I never hear back. It’s reminiscent to my many years of online dating. Is it me? How can I target my search to get what I really want?

— Samantha, Chicago

Dear Samantha,

You only need one! Right? Just one perfect guy/girl in your life to take away your loneliness. Or one dream job to give you true purpose. You aren’t asking for too much. But the slog, the process, the setbacks, the time investment can be a killer. It can be enough to make you want to stay lonely and broke until the end of time. So what’s the catch? What can you do differently?

1. Be focused

Selecting from the onslaught of jobs boards and dating sites on the web is a job in and of itself. Spend a few weeks trying out up to 10 and then narrow down to only two or three.Turn them into apps on your phone so that you can easily access them. Register for the notifications to drop into your email box. And make sure your settings on LinkedIn are doing the same.

However ...

2. Plan when to surf

The worst part of online dating and job searching is that it takes over your life. You easily can become obsessed with checking to make sure you don’t miss a message or a new lead. You know you are in trouble if you are bringing your phone into the bathroom with you.

So instead of letting these searches drive your life and your free time, you drive it. Plan when to surf the web. Say you can do your online dating for one hour on Tuesdays, Thursdays and Saturdays. If it were 1990 you would only be "shopping" for a date when at a party or a bar and that certainly wouldn’t be more than three hours a week. The same goes for job searching.

3. Be picky but practical

So you won’t get everything you want in life we all know this. But you should aim for 75 percent. So you need a list. What are your essential (non-negotiable) criteria? What are your desired? It may be that he/she has to be based within 30 miles of where you live or the commute to the office can’t be more than one hour. Logistics matter in work/dating/life balance. Make a list. Dream a bit. Then get real. Test your list against what you are seeing in the market and feel free to adjust it a bit to reality. However, trust your inner voice. It knows if that job is a stretch or only holds 50 percent of what you really want.

4. It may not do what it says on the tin

We all know that expression “don’t judge a book by its cover.” This holds true for jobs and dates. Recruiters are good at selling their openings. That's their job — to sell their company and the role in order to attract the top talent from the market. Now how often is that piece of paper, that job advertisement, really the whole story?

You need to dig deeper before even applying. Reach out to anyone and everyone you can within the company first to find out what the culture, the leadership, the job is really like before you invest a day in a full application.

Same goes with serial dating daters — they are good at selling themselves. They have had friends and family help select the best photos and whip together some witty description of themselves so that you want to "favorite" them. They may look great on paper but in reality they are just a grown-up kid not ready for a real relationship.

Of course we all want to put our best foot forward but, as my sister recently reminded me, we are on best behavior in the early days of dating, seeking to impress like in a first interview. So those initial texts, calls, dates, photos are going to be the best that it gets. Sounds a bit cynical, I know, but it is kind of true, too. So this means take everything with a grain of salt.

Don’t judge too quickly and do give people a chance both on text and in person. But you won’t exactly be able to vet them through previous relationships like you may be able to a job. So you have to trust your criteria list and your heart on this one.

5. Tell your friends

Did you know that 75 percent of couples meet through work or friends? And 65 percent of jobs are found through connections. So spread the word! Let everyone know what you are looking for, both in terms of the dream guy/gal and in terms of the dream job. Communicate your criteria to the market (friends) and put yourself out there. It is OK to be a bit vulnerable here. People like it when you wear your heart on your sleeve but without looking desperate.

6. Let go of immediate results

The more we crave, the more we strive, the harder these processes can be. Go into the job search or the dating scene with an open yet non-needy sense of self. In both cases, you are the commodity!  Someone out there, employer or date, wants someone just like you. Goals are good to have and we stay motivated by setting them so that they are SMART and achievable. However, some of life is also purely about timing and being at the right place at the right time. Serendipity is still important in both processes. So try to let go of the full throttle.

7. Take the hint

If recruiters think you are a good fit, they will call you! Their job is to get the best person into the role. So don’t take it personally if you don’t get a call. It is likely that the job or company may not be the best fit for you, either. It is a two-way match. Often we think that the company is on the front foot and we, the job seeker, are on the back foot.

But it is a mutual vetting process. It is hard not to take offence in rejection. But it is a bit of a numbers game. The more interviews you have, the more likely one will convert into that perfect match. But if you don’t hear back, take the hint. Feel free to follow up for feedback as it’s always good to get other’s perspectives on how we came across.

Same goes for dating. If he/she isn’t responsive, doesn’t make the move to see you in person, isn’t very available, then probably best to leave it and keep hunting. Again, it is hard not to take it personally. But why would you want someone (or a job) that doesn’t want you anyways?

There was a great book by Greg Behrendt, "He’s Just Not That Into You," that was a first of its kind with tough love advice for otherwise smart women on how to tell when a guy just doesn’t like them enough, so they can stop wasting time making excuses for a dead-end relationship.

8. Give yourself a prize 

So, if for one week you have done steps 1-3, well, you need a reward. Mine is usually a night of back-to-back "Breaking Bad" episodes in my PJs with a glass of rosé. Yours might be a bike ride with a friend, that new pair of shoes you’ve been eyeing or a chocolate cake at the local bakers. Indulge.

Rewarding yourself for committed discipline is important. Make a chart of your week and track your days. Did you stay on target with being focused, planning when to surf and being picking? If you did for a whole week, you get your prize. Celebrate.

Personal note: Having recently separated a year ago, I find myself trying to take my own advice — and to be honest, I am failing terribly. I end up on these online dating sites until midnight instead of reading this new book, "Discover Your True North" — great book, by the way. These bloody phones are so addictive and we know they are sucking us in while we are doing it but we do it anyways.

So my resolution is to take my own advice! 

Please let me know if I can help you convert your dream job into reality step-by-step.

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