Welcome back to The Workaround. I’m Bob 👋
You’re in good company with fellow entrepreneurs and innovators who follow my stories from a career in tech startups and corporate innovation.
I’m here to make you think, smile, and discover a shortcut to success or a trap to avoid.
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Long-distance view from the stadium seats as my daughter waits to collect her diploma. Her hat design is both her favorite movie quote and a motto for her career ahead: “Life finds a way.”
Every month or so, a friend asks if I would be willing to meet with their son or daughter who is very early in their career—usually about to graduate or a few years out—in hopes that I might offer some helpful advice.
Just last week, I met Ben, who is looking for a wealth management position in Chicago.
I’m not sure I’m always helpful, but I always say “yes.” I love meeting people and still remember how much I struggled to figure out the job search game long ago.
It’s rough out there. A study by Handshake—an app for college and entry-level jobs—reports that position openings are down 15% from last year (but applications are up 30%). The U.S. unemployment rate for recent grads is 6% versus 4% overall. Call it AI, economic uncertainty, or whatever you want. But there’s no denying that new grads are now working harder to land one of a shrinking number of openings.
Getting a job is their real first job. And the universities we spend so much money with don’t teach this class.
This summer, my daughter, Ella, had a few weeks to kill before her first job—an internship—began. So I decided to create the class that she and her peers at so many universities never got to take.
My “class” comes from my experience hiring hundreds of people for my companies and running a recruiting business for a few years.
Follow these steps, and I guarantee that your odds of success will rise dramatically. Plus, you’ll build lifelong skills in the process.
There are a couple of things to keep in mind before you begin. The first is to clear out any unproductive feelings and voices in your head that get in the way. For example:
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Accept that life is not fair and the world doesn’t owe you a job.
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Don’t play the game of blaming the economy, government, your university, others’ privileges, or capitalism.
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Avoid self-doubt, including the idea that you need to get another degree of some kind.
These are internal, ego-based defenses that prevent you from seeing reality: First jobs are tricky, and for several decades, almost everyone has struggled through fits and starts to get their careers off the ground.
Trust the process. Then, get to work.
This is the second prep step. Think of finding a job as your 40-hour/week job. It’s all about self-discipline. Things like setting an alarm clock in the morning, getting dressed, and sitting down at a computer by 9 am. Create a goal for the output you want to achieve before stopping. Work a full day, giving yourself a lunch break. Avoid social feeds and gaming with friends until after the self-work whistle blows at 5 pm.
By treating the job search as real work, you’ll increase your odds of finding a great role faster. But just as importantly, the day will pass quickly and you’ll end it with a feeling of accomplishment. This holds off the alternative feelings of depression and worthlessness that fill the vacuum of just waiting for something good to happen.
“It’s not what you know, it’s who you know.”
This might be the oldest advice in the history of business. It was true in the past, and it will be even more true in the future.
It’s a timeless lesson because business is personal—human beings working together for a greater cause. Some people work better together than others, so we go out of our way to understand whether or not a new hire will be a good fit on the team.
Our networks comprise the people we have worked with in the past. Since almost everyone is connected in some way, we go to our networks to find and assess potential team additions. That’s why 70% to 85% of jobs come from networking, and referrals from current employees are the leading source of new hires.
Networking is going to be even more critical in the future, thanks to the spamification of job applications. There’s a technology arms race going on: Some companies make it easier to apply to more jobs, while others work to screen out resumes. Company recruiters open up their tracking software and cringe as they see applications piling up faster than they can look at them. Then their job is to say “No.” All. Day. Long.
You shouldn’t necessarily stop applying, but don’t overdo it and never expect a reply, much less an interview.
On the other hand, networking brings several benefits:
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Learning—As a recent grad, you know almost nothing about how the world of work really works, so talking with people gets that knowledge out of them and into your brain. The people you meet will offer what you’re missing, filtered through their experiences of what worked and didn’t for them. You don’t have to believe or act on all of our advice, but the more you take in, the more you’ll see the patterns of truth and the right path for you.
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Further Networking—Once you meet with people, they often think of others in their networks who might be helpful. If you’ve made a positive impression, they will be happy to keep helping in this way.
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Side Door to Hire—Don’t expect this to happen very often, but the person you network with might be in a position to hire you or tell the recruiting team in HR to pull your application out of the pile for a closer look.
This whole thing is a numbers game. Meet more people, get more of these three benefits, and you’ll increase your surface area of luck. And this is how you’ll continue to discover and land jobs for the rest of your career.
OK, this is the big picture, now let’s drill down to specific steps…
Build Your Personal CRM
It’s essential to get organized around the people you meet. In the business world, many of us use Customer Relationship Management (CRM) software to track current and potential clients and partners. It’s a way to keep notes on who these people are, how you’re connected, when you last spoke, and what you discussed. As I mentioned earlier, treating your job search as a job requires a process and software to do it well.
But you don’t need to buy or learn any Personal CRM software. You need a simple spreadsheet. I worked with my daughter to create a straightforward version, which I’ve turned into a template with examples here that you can copy or download:
Bob and Ella’s Basic Personal CRM Template
Put all the people you know—your network—on this list, including college friends, helpful professors, friends of your parents, and anyone/everyone you’ve ever worked with. Make sure you’ve connected with them on LinkedIn and add that URL here. Then make some notes about the last conversation you had.
Refer back to this document for contacts who might be helpful in times of need. Check in with key people whom you haven’t communicated with in a while. You might even rank this list according to how well you know them or how helpful they have been. The point is that your network will be the most powerful tool in your career, and the better you build a habit around managing it, the more powerful it will be.
Getting Meetings
Now that you’re organized, it’s time to start speaking with people. First, you’ll want to make sure you’ve met with everyone on this new list. And when you meet with them, or through a short email, text, or LinkedIn message, ask them who else they might introduce you to. Getting a personal introduction from a trusted person is always the best way to go—again, it’s the power of networking.
Then you’ll want to do some cold outreach, too. It’s called “cold” because you don’t have that personal introduction working to your advantage. But you can do a few things to try and “warm” up the outreach.
One of the best ways is to find a mutual connection that resonates with the human heartstrings. For example, do a LinkedIn search for alumni of your college who work in roles or at companies similar to what you’re targeting. The shared college experience will help break through the clutter, creating positive memories and a desire to pay it forward to the next generation of graduates. Send them a connection request with a message like:
“Hey, (NAME) – I’m a recent grad at (SCHOOL) and am starting my career. I’m eager to follow in your footsteps. I’d love to get your advice on how to get started. Would you have some time to do a short Zoom in the next week or two?”
Check back daily for acceptances, and follow up quickly by repeating the meeting request in a DM. Offer to make yourself available at their convenience, and send a calendar invite for 30 minutes with a video conference link to their preferred email address ASAP.
Along with shared school, you can try lots of other potential connection points—like hometown, sport/hobby/activity, or church. If they are doing something creative (like this Substack), genuinely praise their work—we all love to be loved.
But most importantly, don’t get discouraged when people don’t reply. Everyone’s busy. Many people need a 2nd reminder message. Some people fear you’re going to try and sell them something (sadly, aggressive sellers exploit every human hook). And other people don’t have an open heart. Remember, it’s a numbers game, and the right people will reply.
When I spoke to my new friend, Ben, about his fears of sending messages that people might find annoying, he admitted that “my fear probably comes through in my outreach messages, which could hurt my response rate.” THAT is the kind of self-insight that you need to win this game. See your fear as an irrational voice, then move past it.
What to Talk About
You got the meeting, the video app is running, and the face of someone older and wiser comes on the screen to speak with you. It’s showtime, and you’re the one who has to run the show. But it’s pretty easy. Here’s your agenda:
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Introduce yourself—Remind them who you are, give a 2-minute summary of your background, what type of role you’re seeking, and why you thought this person might have helpful advice.
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Ask them to tell their career story—This is when the learning begins, and everyone likes to talk about themselves. Listen for things that surprise you or you don’t understand. Follow-up questions often provide the juiciest insights and show that you’re paying attention.
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Ask some key questions that angle toward your goal of finding a job—This is where you’re getting down to business. Begin with general advice points and gradually shift toward specific opportunities. For example:
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How did you get your first job? This current job?
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What would you do if you were in my shoes again?
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How would you suggest I improve my chances of getting into your company?
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Is there anyone else in your network who you think I should speak with?
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(If there’s still time, and this is a good follow-up) Would you be able to take a quick look at my resume and/or portfolio and share any feedback?
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Finish professionally—End on time, thank them on the call, and send a follow-up email or LinkedIn note to thank them again and mention any follow-ups (e.g., “here’s my resume if you have time to take a look” or “I would love to meet with that friend you said you’d introduce me to.”) Then update your tracking spreadsheet.
Get in the habit of this, and you’ll not only rack up more insights and intros, but it’s a way to build up your skills and confidence in meeting new people. Again, this is what your entire career will be riding on.
The job search version of insanity is thinking that you’re going to win against 1,000s of other similarly-skilled and degreed applicants. And while networking can increase your odds, there’s a second strategy hiding in plain sight that almost no one considers. Most people don’t follow it because it requires significant effort. But that’s kinda the whole point…
The secret? Do something creative, consistently, that shows your passion, skills, and grit around the job you want. This will help you stand out in a crowded field while further developing your skills and staving off the depression that comes with waiting for a reply from a recruiter.
I first saw this strategy in action years ago when I was hiring entry-level client service people at my digital agency. The job attracted numerous candidates eager to work at a high-growth, cool, and creative company with big brand clients. I recall sifting through resumes of recent college grads and seeing the same thing: Marketing degrees from good schools and good GPAs.
But then I noticed one candidate, Kristin, who had a side-hustle making and selling men’s neckties online. That got my attention! E-commerce was growing, and I knew that someone with hands-on experience would be ahead of the game. Plus, anyone who can take the initiative and run a side business while carrying a full course load must have a great work ethic.
I moved Kristin to the top of the interview list. I spoke about her with other teammates around the office, pointing out her website, and eagerly anticipating her visit. I entered our interview discussion with incredibly positive vibes. My questions were mainly around her small business, and she replied with genuine energy because it was something she knew well and was excited about.
We quickly gave Kristin an offer. She excelled at our agency for years, and I was lucky enough to recruit her at my next startup, too, where she kicked more ass. I don’t think we would have had such success together if she hadn’t been selling men’s ties online those many years ago.
Here’s why creating something helps accelerate your career:
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Proves Your Skills—It’s tough for a recruiter to tell from school classes and projects if a candidate can do the work companies need. But there’s no denying a public project that came from your mind and hands. And, like Kristin, you learn so much by doing this real-world work. It’s why I prefer portfolios to resumes for almost any job.
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Stand Out from the Pack—Almost no one else does something like this, so when you share it, hiring managers and recruiters spark to it. This project also gives you more interesting material to draw from when you’re getting the standard interview questions.
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Shows You Care—The time investment it takes to do a personal project speaks for itself. Those on the hiring side see that you must be passionate, confident, curious, and motivated. You could do so many other things in your free time, but only the best-of-the-best care enough to do this.
Where to start
First, don’t take on a project unless you love the work enough to keep it going. As I’ve written here before, you’ve gotta care about it. Just one blog post or video is unshareable, as it suggests you don’t have what it takes to follow through.
So find something that you love making. It could be videos, freelance work, an e-commerce business, blog posts, memes, a podcast, poetry—whatever—as long as you are consistently producing and it’s related to the career you’re looking to be in.
An idea I’ve shared a dozen times is for people looking to break into marketing. Let me break the idea down:
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Most entry-level marketing jobs are related to social media management.
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Recent graduates are typically more adept at social media, and this type of marketing is a common tactic to attract young consumers. Net, you probably understand social media marketing better than your prospective employer!
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Create a project that demonstrates your ability to market a brand on social media effectively.
For example, a series of “street interview” videos about what Gen-Z thinks of popular brands. Pull in random people walking on campus, or even coach your friends to deliver the goods you need. Chop them up and edit them using the skills and software you’re most familiar with, then send them to the hiring managers and recruiters at the companies. The great thing about this idea is that it can be applied to any business with job openings. Hell, you can even create a “brand” around “what Gen-Z thinks of brands.”
All you need is one person to watch, and they will—because it’s interesting, different, honest, and NO ONE ELSE DOES THIS SHIT! We sit at our desks doing boring stuff all day, and suddenly we find this remarkable person bringing energy to our business. Someone will see this, get excited, share it around, and suddenly you’ve got an interview in which most of the questions will be around what you know better than they do.
Back to my conversation with Ben, we brainstormed together about interests he has that could be dialed up to stand out in looking for wealth management roles. He told me he’s been using AI to help direct his personal investments. BOOM! There’s an idea! Everyone in the world is trying to figure out AI, and most leaders are too busy with their day-to-day to dig in. But if he packages this interest into something shareable, Ben could stand out and likely be pulled into any one of many companies that are feeling FOMO on AI.
There are many other hacks you can apply once you’re creating content. For example, you could make a podcast about starting a career in whatever field you have chosen to pursue. The audience could be recent grads like yourself, so you’re building up a network of subscribers. Then, instead of messaging prospects to ask for career advice, as mentioned in my Network section above, you invite them to be interviewed for your podcast! Many people respond positively to such opportunities. It makes them feel good to tell their stories to an audience—thus helping people “at scale” rather than through a one-off chat.
Remember, with every podcast you record, post you write, or video you release, you are developing skills, increasing your surface area of luck, and doing something productive and positive. So many wins to pick up here if you commit to doing the work!
Eventually, everything will work out, and you’ll land the job. You’ll feel like a burden is off your shoulders and the wind is at your back. Ahhh….
At this point, it feels natural to drop everything you’ve been doing to land the job so you can focus on the work ahead. But don’t stop the great habits you’ve built!
Continue your CRM. Go back to everyone on that list who helped and send them a personalized email to share your good news and thank them for their support. They want to know that their assistance paid off. Next, start connecting with everyone you can at your new job. Some day you’ll be looking for your next great role, and the more effort you’ve put into building and tracking your network, the more valuable it will be.
Keep the content coming. You might dial down your side hustle work a bit, but you’ve now got a great habit and a following, so don’t let it drop! Again, it’s a chance to keep building your skills in something you’re passionate about. And, just as in networking, by putting more content into the world, you increase the odds that someone will find you for something interesting in the months or years ahead.
Pay it forward. With this job in hand, you’re now in the position to help others who are striving to follow in your footsteps. Always reply to people who reach out to you in the future, and do what you can to help them along. Remember what it felt like when most people didn’t reply, but a few kind souls did. Continue that kindness.
I spent last weekend driving cross-country with Ella to move her into her first job after college graduation, and the irony factor is 10 out of 10.
Thirty-one years ago this month, my Dad made a similar trek with me—to the same state and same city—for my first job. Back then, just as today, the economy was rough, and I struggled to finally get an offer.
But I saw in Ella, and remembered in myself, the excitement of breaking into the real world—of having a chance to test and prove ourselves, and to start carving our futures.
A few hours after giving her that last hug, I received a text from Ella as she emerged from a new-hire orientation session. She went up to meet with both speakers at the session, having already connected with them on LinkedIn, and got some great advice.
Then she emerged from the building to the sight of a giant rainbow. We agreed it was a sign from the universe of great things to come…
If you like my writing, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏
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Fleet is our holding company for services businesses. We invest in leaders ready to start their own companies (we also do some M&A). If this might be you, hit my Office Hours link.
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A2 Influence is our content development agency, helping some of the biggest brands and retailers create and distribute authentic content at scale.
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Revelin is our consulting practice that helps with revenue alignment, growth management, and other RevOps functions.
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Feel free to schedule a chat during my Office Hours to discuss questions, feedback, networking, or any other topic. Seriously, any topic! You can also reach me on LinkedIn or by email.
A little something I found meaningful. You might agree…
Career Tip: Take the Steepest Slope
I’m not the only one on Substack sharing personal tips that we wish someone had told us at the start of our careers…
My favorite recent example comes from Avni Thompson, who writes regularly at 10,000 Ways. In her post, “Maximize Slope,” Thompson shares the number one question recent grads ask her: How do you choose among so many potential jobs and career paths? Her answer: Pick the direction that is going to give you the steepest learning curve.
She goes on to share stories from her career and lays out how diving into juicy, unknown challenges helps build skills quickly, learn how the business world works, figure out what type of work is best for you, and gain confidence to keep taking more, bigger risks—which end up paying off in so many career opportunities.
The future of work probably isn’t going to be comfortable. Getting comfortable with discomfort might be the key to success from here on out. And the earlier we learn to do this, the longer we’ll get to benefit.
