Afraid of Success

cold feetDear Coach Chris,

I am a skilled craftsman.  I have built, remodeled, renovated houses and businesses for 16 years.  I want to start a legitimate, successful business where I have binding contracts, a dedicated, skilled crew and I want the role of project manager/owner, not the primary laborer.

I am a hands-on manager and end up doing a lot of the labor even when I have a small crew to help me.  I am always afraid the project won’t be completed to my standards and want to control the results.  Most of my projects are done through a “gentleman’s” agreement.  I have to admit the financial agreement sometimes becomes a problem but overall I have a manageable income. Through the years I have established a good reputation for my work.

I don’t have a BIG picture plan for my current business.  I basically try to estimate the projects and most of the time I do profit but there have been times I complete a project at a loss because of some poor estimates and unforeseen issues.  It has been a struggle attracting and keeping quality craftsman because I cannot promise future projects.  It is difficult to estimate future projects and also be on the job site.

I fear if I change anything my current success will end.  I fear I will not find a dedicated, qualified skilled crew.  I fear there is so much to learn about the taxes, insurance, employee benefits, and all of what goes into owning a legitimate, successful business.  The thoughts overwhelm me and keep me stuck.  I begin each year with a plan but never pursue the next steps.  How do I move past my fears?

Cold Feet,


Dear Cold Feet Craftsman,

Congratulations for the current success of your “by the seat of your pants” business and I do agree it may not be sustainable long term.  Through 16 years I know you have learned, overcome and experienced many business situations and issues.  You can now utilize these skills along with your craftsman skills to add to your “legitimate” business.

Owning a successful, “legitimate” business has its challenges but there are many resources you can tap into to learn how to legitimize your business.

  1. Talk to other similar business owners.  They can sometimes share the lessons learned and possibly refer other resources.
  2. Make the time to sign up for business workshops.  Most of the workshops will provide information on how to market your business, the types of insurance your business should carry, interviewing and hiring advice, tax information, how to manage and track your project money.
  3. Consider hiring a bookkeeper or administrative assistant if this is not your strong point.

There are many facets to a business. The first and probably the most difficult is establishing yourself as a reliable, quality, skilled craftsman. Guess what?  You have already successfully achieved your reputation.  Your successful past experiences have given you a solid foundation for the next business level.

It is easy for me to say don’t let fear get in your way but consider this; Fear is usually based on stories we are telling ourselves and the more we become comfortable with our stories the harder it becomes to believe anything else.  We can falsely rationalize and bend the facts to fit our fear so we can validate what we believe.  So, revisit the story you are telling yourself and get down to business. You can design and build a house, you can design and build a successful business with the same attention to detail.

Happy Building,

Coach Chris

Hang on to your desk

managerDear Coach Chris,

I was recently promoted to supervisor, a position I worked hard to achieve.  The problem is now I am responsible for my "used to be" co-workers.  A couple of them are very good friends.  We would party every weekend, gossip about the people in the office and share just about everything.  I consider them great office buddies.

During the job offer conversation, my boss mentioned she was aware of the close friendships I had with my co-workers.  She said my role as a co-worker to supervisor can create problems.  I was now their boss and I needed to always be aware of how I am interacting with everyone.  The first sign of favoritism towards my friends would be the beginning of a breakdown of my authority as their supervisor.

I am now confused on what to do.  One of my goals was to be the supervisor.  I am aware of the increase of responsibilities and I am prepared and ready to take on the job.  At the same time, I know my role as "weekend friend" has to change.  My boss included examples: only going to lunch every day with only the select few would create perceived favoritism - something my friends and I always did; internal company conversations needed to be kept between leadership and supervisors; the possibility of having to discipline one of my friends.  The list of what not to do has me questioning so many things.

I don’t want to lose my friends and at the same time I worked for this promotion and don’t want to lose this opportunity.  Can I have both without jeopardizing friends and job?



Dear Sad Supervisor,

Congratulations on your promotion to supervisor.  I agree it is a challenge to draw the line between people who were your co-worker friends to now your staff.  Unfortunately, your new role will impact your relationships.  Included with the increased role as supervisor you are now responsible and liable for the performance outcomes of your staff.  This can sometimes get sticky if one of your “friends” needs to be counseled.  Your staff is always aware of what you say and how you handle every situation.  It is important you maintain your authority because your staff now represents you.

I recommend you have a heart-to-heart conversation with your weekend buddies.  Explain to them your concerns.  Collectively there may be an understanding and possible solution. They need to be aware of your new role and responsibilities. You will be required to make decisions they may not always agree with. I hope your boss will continue to mentor you through some of the trials and tribulations of being a new supervisor.

You obviously have what it takes to fulfill the role as supervisor.  It is a critical role in any organization, and you earned your place.  There will be times you are pulling your hair out and times you will be sharing accomplishments.  So, hang on to your desk because the ride as supervisor is challenging and rewarding.

Continued Success,

Coach Chris

First Date Catch

bad dateDear Coach Chris,

How do I get over my first date awkwardness?  I have had several first dates but never a second date.  I don’t know what I am doing wrong. I am usually very nervous and self-conscious.  I try to over prepare so I can be ready for anything. I know first impressions are important, so I always try to show my date I am a great catch. I always show-up cleaned-up, use my best cologne and arrive with flowers. I make reservations at the best restaurant in town. Most of the time I feel like the date was a good time but when I ask for a second date is ends up with a no.  I feel very rejected and defeated.  This has affected my confidence and I am now afraid to ask another person out for a date.  Should I just give up dating all together?  Help!!!



Dear Awkward Andy,

I understand the awkwardness of trying to impress a first date. When you place an uncontrollable expectation on a date, it will always create doubt and nervousness.  I believe first dates should be simple and easy. This may help with the nerves and confidence. When you go all out for the first date what is left for any future dates?  The first date should be about learning who the other person is.  You can also be the “great” catch by showing interest in your date through conversation.  Many people love talking about themselves.  Prepare some casual questions you want to know about your date and let them talk.  This usually can generate questions from your date, giving you the opportunity to reveal who you are. Avoid dominating the conversation.

So, keeping it simple can open up the opportunity to see if you are compatible with your date.  I suggest a coffee shop, a drink in a quiet bar, or somewhere you can have a casual conversation.  Based on relationship data you will have instant attraction or no attraction in a matter of 15 minutes. Don’t try to force the attraction. A simple initial meeting for a drink will not only save you money but also time.  If you find the initial meeting evolves into wanting to spend more time together, you can suggest an activity - a walk, bowling or something of interest you both have agreed upon.  This can progress to dinner or making plans for another date.

Finding the right person to spend time with is a journey in itself.  Keep dating and meeting as many people as you can.  The "no" to a second date is usually a gift because in the long run it was not meant to be more.  The key is to get to know them before you jump in ready to give your money, time and all of you.

You got this!!!

Good Luck,

Coach Chris

p.s. maybe tone down the cologne?

A Loss for Words

third eyeDear Coach Chris,

My girlfriend and I have been together about a year and I feel like we can talk about almost everything.  I truly care about her and want to possibly have a life-long relationship.  We have a lot in common and get along great MOST of the time except when the word LOVE comes up.  When she first said the words, I love you, I felt a weird, sinking feeling inside.  I couldn’t respond with the same, I love you.  I smiled, kissed her and said thank you. I care deeply for her and feel guilty about the struggle I have saying the words “I love you” back.  She has asked me if I love her, and I just respond with a yes.

I know once I say those words the meaning comes packed with promises and commitments.  Which I think I am ready to accept. Unfortunately, I am still carrying the damage of my past relationship where I was the first one who said the words.  My belief when I said “I love you” to my ex, I had an expectation she was ready to make a long-term commitment to the relationship.  The pain of that break-up still haunts me.

What if once I say the words “I love you” back to my girlfriend and the relationship falls apart? I'm afraid of being devastated again.  If I tell my girlfriend about my struggle it might create doubt about our relationship. What should I do?  I am at a loss for words.


Lost for Words

Dear Lost for Words,

What if she doesn’t commit to a long-term relationship?

What if she DOES keep her promises and commitments?

What if she turns purple and grows a third eye?

You can’t live on the "what ifs" because "what ifs" are infinite.

So, you said you and your girlfriend can talk about almost everything.  I suggest having a conversation about the “I love you” words with her.  You may find the result may create more of a connection between you and your girlfriend. The conversation may help you move forward.  You will both learn what "I love you" means to each other.

I agree when the special words “I love you” are said in a relationship they should be real and used with care from the heart because the impact can be interpreted many different ways.  Your interpretation is a good one, to keep promises and commitments.  I hope you are currently showing your girlfriend this is who you are and not letting the past hold the good person in you back.

Communication is always key,

Coach Chris