My Top 10-ish Points on Starting Your Career (or Re-Starting, Again)

Digging out from a backlog of “sort it out later” emails, I came across some career advice I shared with some up-and-coming professionals. They all got bits and pieces of what follows, but the consolidated list is probably more useful for those with big changes still ahead of them. (This lacks the witty elegance of a Vonnegut-esque commencment speech, but you did’t expected that.)

1. Be honest with yourself, and start doing what you love now. I know that everyone has expectations of what you could and should do, but starting (or re-starting) your professional adult life is a great time to think about who you want to be for you.

Ask yourself, “What do I like to do with my free time?” or “What would I do for free if money wasn’t an object?” or “What would I do if I could be anything for a day without constraints?” When you free yourself from expectations (your own and those of others), you’ll begin to hear your inner voice giving you solid advice.

2. Be prepared to be honest with prospective employers too. You can be confident, willing, and ready, but don’t start a new relationship with half-truths (this is good advice outside the job setting too, but you knew that already, right?)

This requires a bit of due-diligence on your part, too, which is where informal interviews come in (see below). If earning an income is more about supporting a non-work passion, don’t make false commitments to a company that needs you 60-hours a week. Equally, if you are hoping to have a beach house in Malibu, don’t expect to work a 40-hour-week and get there on 5% annual performance raises in the corporate world. Size your passions, and pursue accordingly.

3. Remember that life is a gamble, and you only get rewarded for the risks you take. I’m not suggesting you do something totally outlandish, but you should keep in mind that the perfect job isn’t going to show up on your doorstep, asking you to apply.

Odds are, the “perfect job” at 23 is going to be very different at 32, and again at 45. “Perfect” will change over time, so think about the reward (aka emotional, intellectual, professional, financial) that you may only be willing to risk everything for at this stage of life.

As I get older, I find myself asking if I’m taking enough risks. My few regrets are less about what I did do, and far more often what I didn’t do. Go for your “perfect” today, but be mindful that it can’t compromise your future.

4. Sadly, it isn’t “what you know,” but “who you know” that can make all the difference. (Also thought of as “Spray and pray” isn’t going to get you employed.) Once you’ve given it some honest reflection about what you are willing and able to do successfully, let everyone know.

Your parents, their friends, the neighbors, people at church, and even the random people you chat with in the park. In small and large companies alike, getting your name to the right person at the right time trumps a platinum resume every time.

5. You can’t have too many “informational interviews” when you are thinking about what to do with your professional life. Your chief job right now is to be a conversationalist – be an engaged listener, active and present participant, and follow-up with hand-written “thank you” cards.

Talk with as many people as you can earn a living doing things that sound the even the least bit interesting to you. You never know where that magical opportunity will come from, and at the least you begin making a wide number of professional connections.

(A bit of an aside – not all professional conversations are professional, and not all personal conversations are personal. I think the difference between “professional” and “personal” is based first on the nature of the conversation, and second on the types of interactions between people. When you are looking for work or the next big opportunity, you need to be having more professional conversations than personal. The interactions will come – either on the job, or as you mature and become a larger consumer of professional services.)

6. Come to the search effort with a learner’s mind, a measure of humility. Remember that everyone you encounter likely has more work experience than you – in balancing work and life, running small businesses, navigating organizational politics, or getting along successfully in work groups. You can learn a lot everywhere you turn. Everyone has been in your shoes before.

7. The job market is always good for those with passion, tenacity, and a willingness to be a humble learner. No one works in “the market” – we all work with and for people, in organizations that a multitude of exciting and mundane things.

The same traits I look for when hiring experienced resources are those that help a new professional get started. (These are also traits that I hope to demonstrate when meeting potential clients and collaborators for the first time.)

(a) Are you personable? Could I imagine working with you all day, every day, for years on end? (You should be asking this yourself of every person you meet, too). You want to be seen as pleasant enough to be around – full stop.

(b) Does this person have a passion? It may not be work, but they have to have something that is central to finding happiness in life. We all want to surround ourselves with bright capable people, and passion = interesting, which goes a long way.

(c) Do you seem like a person that sticks with a tough task? Job hunting can be hard, but so are a multitude of other really important tasks. Most potential employers will want to know that, if given the accountability, you can be counted on to get the work done. Demonstrating this attitude from the start goes a long way (remember, only one chance to make a good first impression).

(d) Do you have a learner’s mind? That is, are you open to the idea that you may not already have all the answers? The best experts I know manage to maintain an openness to fresh ideas, even if fields of expertise where they have 20+ years of history and practice.

8. If you are just sitting around wishing for work, volunteer in your community. It will get you out of your house, circulating with people and feeling like you’re doing something good. It will also bring you in contact with people you wouldn’t otherwise meet, which increases your odds.

9. Start building a work track record of something. Odds are you need money anyway, so find odd jobs or sling coffee for a while. Even in the worst job markets, I’ve been impressed with the integrity and commitment that people have shown by taking not-so-perfect jobs while they prepared for that better opportunity. Sitting around all day dreaming about what could be won’t get you there. You want to write? Write. You want to be a professional speaker – get out there. You can begin becoming your better future self now (kind of a spooky thought).

10. You should always be creating more options for yourself. Think about your career as a performance portfolio – one in which expertise and breadth create more options. Everything we do ultimately factors into how we see the world, so don’t dismiss the less “professional” experiences you gain.

If you are going to be a barista, become expert on the nuances of coffee, and pour with artistic flair. If you are going to swing a hammer, learn how your work fits into the larger project and understand what characteristics distinguish a “journeyman” from a craftsman.

If an opportunity presents itself that allows you to explore, grow, or discover new things about who you are becoming, and creates a better series of future alternatives than the course you are presently on, it’s probably a good bet.

11. Show kindness to those you meet today. Know that every interaction you have may be with a future customer, supplier, collaborator, employer, or employee. The world is a very small place, and getting smaller all the time. My wife asks my 8-year-old son each day, “Did you treat people with kindness today,” which seems like a really good question for all of us.

What you do today, and the impressions you make, contribute to the reputation you have going forward. With a hat-tip to the famous Warren Buffett quote, “Don’t do anything you wouldn’t want your grandmother to see on Facebook.”


I’d love to hear from you too – what is some of the best advice you’ve given or recieved? Did it make a difference in how you approached your career?

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1 Response to My Top 10-ish Points on Starting Your Career (or Re-Starting, Again)

  1. Tina says:

    I am happy to find your blog. This is exactly what i needed to read today, it was very inspiring and motivating.

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