How The Right Mentor Can Transform Your Life

The best ones don’t advertise on the internet

Photo by CoWomen on Unsplash

A mentor once rescued me from near bankruptcy. He didn’t save me with a job, a handout or a lifeline of any sort. It was thoughtful advice, hands-on coaching, and quality feedback about my strengths and weaknesses.

My business had collapsed, and my bank account was racing towards zero. I had been out of the job market for two years — the textbook definition of unemployable.

My mentor at the time was coaching me on strengthening my sales skills. I had improved at selling but not enough to rescue my nascent business.

I came clean with him and told him I needed a job — one that produced a paycheck. He helped me craft a game plan, worked with me to prepare cold-call and pitch scripts, and acted as a training partner.

A month later, I had scored a six-figure job I should never have gotten. I was laughably unqualified against stiffer competition. My mentor made that outcome possible. Fourteen years later, I consider it one of my most significant accomplishments.

What will a mentor do for you?

Mentors can fuel your growth in business, work, relationships, and almost any other domain important to you. A solid working relationship will yield profound benefits.

  • A good mentor cuts years off your learning curve by pointing out mistakes you’re too inexperienced to notice.
  • A good mentor gives you honest criticism about the quality of your work.
  • A good mentor points out options you would never consider.
  • A good mentor gives you advice but won’t make decisions for you.
  • A good mentor won’t spare your short term feelings if they believe it will benefit you long term.

Where do you find a mentor?

Mentors come from three sources: corporate programs, family and close friends, and private arrangements with outside experts.

Be wary of the corporate mentorship program. They impose conditions on your participation. You will bear additional responsibilities and expectations you might not otherwise agree to.

Corporate mentorships also come with conflicts of interest. What’s best for you is not always best for your organization. Your mentor might feel conflicting loyalty.

About that rich uncle

If you’re lucky enough to have a successful aunt, uncle, or family friend, beware. It’s hard to play the role of the objective third party when there’s an existing relationship.

They want to keep relations comfy and avoid hurting your feelings. That makes it more challenging to tell you the uncomfortable truths.

Private mentorships

I’ve paid anywhere from $700 — $12,400 for my four paid mentorships. Does $12K sound like a lot? It did to me, but this was the mentor who coached me to that six-figure job when I was broke and unemployable. So, yeah, it was worth it.

Think of the fee as an investment, not an expense. Expect to receive a return on your investment. The investment fee also motivates you to work hard and recover your investment.

How to not get screwed on your mentor investment

Creating a successful relationship requires due diligence, realistic expectations, and the right attitude. These guidelines will help you get the most out of your experience.

The best mentors don’t advertise on the internet

They’re not begging for business. If you try to hire them, they’ll tell you they’re too busy. It takes several attempts and a bit of cajoling to win their acceptance.

Don’t let that scare you. Would you rather have a mentor who’s begging for business or one in high demand?

See them in action first

Be sure you vet a prospective mentor’s qualifications. Anyone can script an inspirational rendition of their self-proclaimed prowess.

It helps if they have a reputation within your sphere of interest or industry, but don’t rule out someone just because they’re unknown. I had never heard of my first mentor, but he changed my life.

Chemistry matters

The mentor-mentee relationship will live or die on chemistry. If you’re someone who thrives off of direct, no holds barred feedback you’ll get frustrated with a mentor who gives flowery, subtle wisdom.

A short and inexpensive engagement will help you assess your mentor’s qualifications and allow you to determine personality compatibility.

Compare your goals to their expertise

What do you want out of this relationship? What is your mentor qualified to provide? You should already know your mentor’s general qualifications but get into specifics before you shake hands.

Be upfront and clear about where you need to grow. Ask if they can assist in moving you towards your goals and objectives. Can a potential mentor lie? Sure, but a few pointed questions should help flush out the truth.

“I’m not looking for free consulting here, but my goals is [x]. How might your experience and expertise assist me in reaching these goals?”

No conflict of interest or shared interest

Don’t hire a competitor as a mentor. That’s obvious. But keep in mind, a conflict of interest may not be readily apparent, especially in the freelance world. You could find yourself hiring a mentor who fears you might compete for the same clients once you improve your skills.

The same advice holds for a mentor with a shared interest (you both benefit financially from an outcome). Your mentor may approach your relationship with the best of intentions, but a shared financial goal might adversely influence his judgment. Like the corporate mentor, he may advise you to do something that advances his interest at the expense of yours.


I once had a copywriting mentor who reviewed my sales letters. Before the money changed hands, he voiced a pointed warning.

“I will not, under any circumstances, rewrite your work. I will only point out flaws. It’s up to you to rewrite.”

His delivery could have been better, but the point was clear. He had set a boundary, and I had better not deviate from it. Ask your mentor about their boundaries. What kind of assistance is off-limits? Better to understand at the beginning, than feel cheated or resentful later.

Hands off their network

Your mentor likely boasts an impressive network of friends, associates, and peers. Wouldn’t it be nice to get your hands on her contact list? How about a personal recommendation from her?

Most mentors guard their network like treasured family heirlooms. Don’t make things awkward by pressuring them to make an introduction. Instead, do impeccable work. Demonstrate a solid work ethic. Act with integrity.

Do these things, and they may offer to open up their contact list to you.

They’re not there to handhold you

Think of the ideal mentor as the ideal teacher; they give you just enough information to figure out the solution yourself.

There may be some exceptions, but a good mentor will guide you and help you choose the right path. Your mentor can leave a trail of breadcrumbs, but it’s up to you to find your way out of the maze.

Most important…

Your mentor will tell you things you don’t want to hear. I recently threw out 70% of a project I had been working on for over a year. It hurt to receive that feedback.

I felt an urge to blame him or dismiss his criticism, but I restrained myself. I knew he was right; my new path would ultimately lead to a better outcome.

Before you lash out at their constructive criticism, remember why you hired them in the first place.

Experimenter in life, productivity, and creativity. Work in Forge | Elemental | Business Insider | GMP | Contact: barry@barry-davret dot com.

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