Should you reach out to strangers for career advice?

Question

Rich Dad · Accepted Answer

Your next opportunity is probably hiding in someone else’s inbox.
Let me be blunt: closed mouths don’t get fed — and closed networks don’t get rich. If you’re waiting for permission, referrals, or some HR portal to change your life, you’re playing the smallest game possible. Reaching out to strangers for career advice is one of the highest-ROI activities you can do — and it costs exactly $0. A single 20-minute conversation can compress 5 years of trial and error into a single afternoon. I’ve seen it happen.
Look at real-world examples. Countless tech founders landed their first roles or co-founders through cold outreach on LinkedIn. Sales professionals regularly close six-figure deals by emailing people they’ve never met. Venture capitalists invest millions in founders they met through warm-ish introductions that started as cold messages. If people can raise $5 million from strangers, you can certainly ask for career advice.
Now here’s the strategic part — don’t be needy, be valuable. The mistake most people make is sending a vague message like, “Can I pick your brain?” That’s amateur hour. Instead, be specific and respectful of time. For example: “I’m transitioning from accounting to product management. You made that shift in 2018. Could I ask you 3 specific questions over a 15-minute call?” Notice the clarity. Professionals respond to precision. Aim to send 10 thoughtful messages per week. Even a 20% response rate gives you two conversations weekly. Over 3 months? That’s 24 industry insiders in your corner.
And here’s the uncomfortable truth: your job applications are competing against referrals. Studies consistently show referred candidates are 3–4x more likely to get hired than cold applicants. That’s not fair — but business isn’t about fairness. It’s about leverage. Every conversation increases surface area for luck. One person mentions an opening before it’s public. Another forwards your resume internally. That’s how insiders win.
Now, could you embarrass yourself? Sure. Some people won’t respond. A few may ignore you. Good. Rejection builds calluses. Wealth builders don’t fear silence; they fear stagnation. The worst-case scenario is a non-response. The best-case scenario is a mentor, a job, a partnership, or insight that saves you from a $20,000 career mistake.
If you treat outreach like planting seeds — consistent, intentional, value-driven — you’re building a network that compounds just like money at 10% annually. Five years from now, you won’t remember the awkward messages. You’ll remember the doors that opened.
Opportunities don’t knock — they respond.

Poor Dad · Answer

Not every stranger is a mentor — and not every door is safe to knock on.
I understand the appeal of reaching out to strangers for career advice, but please be careful. The professional world still values structure, reputation, and boundaries. Cold outreach can work — but it can also backfire if done carelessly. People are busy. Senior professionals may receive dozens of unsolicited messages every week. If your outreach feels generic or pushy, it can damage your credibility before your career even begins.
Instead, I recommend a safer, more strategic approach. Start within your existing circle: professors, alumni networks, former managers, family friends, professional associations. These “warm connections” are far more likely to respond. For example, many universities have alumni directories where graduates explicitly agree to mentor younger students. That’s very different from messaging a random executive on LinkedIn. The response rate in warm networks can be 50% or higher, compared to perhaps 10–20% with true strangers.
There’s also a safety consideration. Not every person offering advice has your best interest at heart. Some may give poor guidance based on outdated experience. Others may try to recruit you into questionable business schemes. I’ve seen young professionals persuaded into commission-only sales roles or risky startups because a charismatic “mentor” convinced them it was a shortcut to success. Always verify credentials. Check career history. Look for consistent, stable progression.
Additionally, think about professionalism. If you do reach out, be concise, polite, and patient. Never demand time. Never follow up excessively. And prepare before the conversation. Research the company, the industry salary ranges, and the career path. If you ask questions that could have been answered by a 10-minute Google search, you risk appearing unprepared. Preparation shows maturity — and maturity builds reputation.
Finally, remember that career success is built over decades, not through one conversation. A stable job, steady promotions every 2–3 years, continuous skill development, and consistent savings into a retirement plan can lead to financial security. Networking is a supplement — not a substitute — for competence. Focus first on becoming excellent at your craft. Then outreach becomes easier because you actually have value to offer.
Be thoughtful. Be selective. And protect your professional image as carefully as you protect your savings account.
It’s better to build a reputation slowly than to damage it quickly.

Should you reach out to strangers for career advice?

Rich Dad Says

Poor Dad Says

The Bottom Line

Whose advice would you follow?

Share this debate

What do you think? (0)

More debates