Midlife career transition starts at age 18: seven suggestions to build your reputation

This is a guide for people at all points in their careers who hope to someday hit the road solo. I hope they’re helpful in bringing you to a point in your life where you launch a new career based on the experiences you collect and the pathway that leads you to your passion.

Age 18–20: Start somewhere.

You may still be in school, but understand that everything you do will potentially add to your future marketability. If you’ve got the chance to take on work-study related to your field, so much the better (I worked in my University’s graphic design studio as a junior, which led to a summer freelance business and ultimately college credit). Internships are unbelievable opportunities to gain experience and impress working adults, but also to build your networks for the next step.

You may have what you think is a crappy job that will never lead to anything. If you believe that, it will most certainly be true.

Think instead of how you’ll tell a particular story on your resume, or in interviews. Find the moments that were impactful for you, what you’d learned as a result, and keep those stories foremost in your mind. If they’re hilarious, so much the better. If you’re afraid you’ll forget them, start a file wherever you’ll be able to remember it: online, in a drawer, sketchbook, etc. Test and refine these stories with your friends so they’re concise and impactful when talking to potential employers.

Age 21–26: Bust ass.

You’re out of school, with looming student loans. You’ve already learned to work hard, suck it up and look for the good in every situation. So when you start your first job, doesn’t matter what it is, stick to it and work hard for the first five years. This is where you begin to establish your network and reputation as a dependable, smart, resourceful and curious person. No matter what they throw at you, take it: any opportunity to learn something new, share it with others, attend a conference, train a newbie, jump through hoops for a client, volunteer to make a presentation. It all adds to the career bank account, from which you’ll withdraw later in life. At the start, make those deposits early and often.

This is not to say you should stay at one job for five years. Everyone knows you’re gaining experience and you should think of yourself as a free agent of sorts. If you find you’re in an untenable situation and need to switch jobs, or your initial search leads to better opportunities that open up, make sure you leave each position on as good a footing as possible. Even if your boss was a total dick, she or he will someday need to provide you with a reference, probably sooner than later.

Train your replacement. Leave lists of things to remember. Clean your desk and your file drawers with Windex so the smell of Jack-Links is long gone when they take over your old space.

Finally, save your venting for beers with friends, and certainly don’t flame anyone on social media no matter how justified you may feel once you leave. Hitting “post” in that situation could cost you some serious future dollars, from an employer that could see you as a potential problem.

Age 27–32: Be Normal.

If you play your cards right, you’ll have opportunities. If you’re in any sort of position that allows you to network with clients or peers, volunteer, head to conferences, serve on boards or hobnob, you’ll be the one out there shaking hands, buying drinks, telling jokes, networking. Or accepting those from people who want to get your attention, do business with you, send a little swag your way.

I cannot state emphatically enough that you need to be normal.

That means, regardless of how many drinks Sheila has had, how hot and single Mario might be, how easily that third vodka soda might go down, you need to stay in control. Be the adult, keep it together, and for God’s sake don’t do anything that would compromise your integrity. Or your pants. Or your parental status. Or your marital status.

You want people to tell good stories about you all the time. You want those group selfies to demonstrate that you’re fun, you’re a team player, you’ve got a wicked funny sense of humor and hysterical stories from junior high roller skating parties but you are anything but the office souse or the office skank.

Karma can be a real bitch. Or she can be a loving, nurturing mother. It all depends on how you choose to live your life. Live it right, please?

Work is work, and life is life, and opportunity is opportunity, but this is work, not love. Tell yourself that ne’er the twain shall meet, especially on the road at 1:30am with someone you’ve just met.

Age 33–40: Connect everyone.

Now that you’ve established the fact that you’re smart, hilarious, normal, you love your partner [and you tell stories about her/him/they almost non-stop and that there’s no chance of hanky-panky], it’s time to pull out the swiss army knife of career opportunity: connection.

If you look for the opportunity in every situation, you will be seen throughout your life as “that person” who keeps the conversation going, either in person or online. This is not some innate genetic trait given only to those with clear eyes and square jaws: this is a skill that is acquired through experience. And yeah, you need to put yourself out there, early and often.

If that’s hard for you, take a look in the mirror before you leave the bathroom: first, check your nose for errant organic matter, then look yourself in the eyes and tell yourself that you’ve got ideas, you can help anyone, you can be the person that, through simple hustle or forethought or plain old goodness might be the one that leads another person to a career breakthrough. Or vice versa.

It’s all about the conversations you collect, the relationships you foster. Being interested, being curious pays dividends regardless of whether or not it benefits you personally. People want to have the opportunity to talk about themselves, to tell stories if you will only ask.

Whether you agree with this or not, it always helps to have a glass of something intoxicating in your hand when these conversations occur. Social lubricant has been cementing business relationships for centuries, and there’s no reason to question its validity at this point.

Go with it, but remember what the hell you agreed to do with your pants in the previous section.

For those of you who have real problems with That Devil Alcohol, you already know that a glass of club soda with lime pretty effectively substitutes for a hammer in these situations. Drink as many as you like!

Finally, save your competitive spirit for the softball field. In the game of professional connection, there is no competitor that might not somehow, someday help you in return. At the very least, you can compare notes on the project you both went for, or maybe commiserate about a technology issue that you deal with regularly. Validation is a huge part of connecting; make it count by being part of as many conversations as possible.

Seek out the awkward conversations: find the scariest looking old guy in the room or the most fierce competitor or maybe even that dick of a boss you used to have. You will find that if you approach these conversations openly and with your energy level high, you’ll both benefit — and you’ll be the one that started it all. Good for you! Good for everybody!

Age 41–49: Differentiate.

You have to be really good at something. Something that people really need or care about. Something that differentiates you from everyone else. I know a CEO of an international product design firm that regularly sends out birthday cards — yes, real cards with real handwriting and postage stamps — to people in his network. When he meets someone new, he makes a point of asking when their birthday is, and makes good on his promise year after year. That’s differentiation, but it’s not a gimmick. It’s an authentic reflection of the caring person that he is.

Think about what that might be. Are you a great mediator? Do you have the ability to think quickly on your feet? Simplify complex concepts as you draw them on a whiteboard? Are you one of those creative thinkers that’s always pulling puns out, because on a dime you’re able to spin a phrase around or create an ironic twist? Do you automatically edit someone’s grammar as you’re listening to a story on the radio? Can you bake unbelievable creme de menthe brownies?

Whatever it is, other people will admire, appreciate and remember someone who is authentically differentiated.

Okay, so how can you tell what your specific skills are? By asking those closest to you whether the ones you identify are truly yours. And if you’re not sucking the oxygen out of the entire conversation and making it all about you, the inquiries you make should be a pleasing give and take, a building up of each other’s strengths and an appreciation of what makes the other person unique, as well as you yourself.

Give it a try with someone you love, someone you admire, someone you wish to emulate. These may come unsolicited as you reach out in your network, and may surprise you.

Any age: Give first.

You can work hard, be normal, think of connecting others and be uniquely differentiated with your peers and networks, but the most important thing about all of the above is your “heart position”. If you’re only in this thing for yourself, for what you can get out of it or how much profit potential there may be, you’re thinking about it all wrong.

People can smell a rat immediately. You can, too.

You know the person who spends lots of time giving themselves backhanded compliments, who twists conversations inexorably back to their interests, who yawns (or worse, walks away) when other people start to contribute? The ones that immediately interrupt to tell you how much better, or worse, or “OMG you have no idea” they’ve had it? Don’t you hate that?

Instead, focus on the specific things that differentiate you, how those make you uniquely helpful to the person in question, and soak up the information you receive. Whether or not it benefits you financially, you’re still ahead because you’ve learned something new by helping someone think through a particular problem or connecting them to someone else that might be laser-focused on that person’s need. Either way, the solution came about because you invested in the other person and put their needs first.

Age 50+: Learn Forever.

This has been peppered through this post, but understand that regardless of the situation, you can learn something of value. Listen to podcasts as you commute or cook. Read voraciously. Engage in inspiring conversations with people you admire. Invest in making in-person connections with authors of articles/blogs/books you read, and tell them how inspiring/hilarious/amazing you believe them to be. I bet they’ll respond in kind.

To be able to survive in business, you can’t always depend on the big haul, the $250K design project, the massive influx of customers who are clamoring for your products.

My new philosophy is to approach even the smallest of interactions with a mindset that presupposes personal benefit regardless of the topic, medium or person I’m learning from.

I am a notoriously bad business book reader (if your bed stand is stacked with these types of books, more power to you). Instead, I create learning opportunities where I can: e-books that I listen to while taking that long drive; podcasts that I flip on while I’m washing dishes. A chance meeting at a graduation party. A conversation with the person at a hotel desk. A new series on Netflix. It’s all good, and it all adds to your ability to learn from others, tell stories that engage them, and contribute to the greater good. Learning never stops. If it did, what fun would life be?

At age 51 I started my midlife career change using the reputation-builders above. I’ve been fortunate to have a number of bosses that believed in me and allowed me the leeway to explore, learn from others, and build a network of good folks that now support, encourage and employ me.

It’s been a wild ride, thoughtfully built on a foundation of solid planning. Send me your thoughts, I’d love to learn from you!