Apply Your Business Strategy to Your Love Life

Article by:
Barbie Adler, EO Chicago
Barbie Adler
EO Chicago

Barbie Adler, herself an entrepreneur, is a respected relationship expert and the founder and president of matchmaking firm Selective Search Inc. For more information on Selective Search or Barbie Adler, visit

For most entrepreneurs, the prospect of dating or finding someone meaningful to share your success with lands on the "To Do List" wedged somewhere between "Find a CFO" and "Add CRM to the database." Our personal lives have a tendency to meld seamlessly with our work life until it’s hard to discern the two. The concept of work-life balance feels more like a distant galaxy than reality.

The question I’m most often asked is, "Where are all the quality singles?" The honest answer is that they are all around you. But finding someone of substance takes the kind of time most entrepreneurs don’t have.

So apply your business practices to your search. Approach dating like you would finding a new employee. Be your own recruiter. Don’t leave it up to blind dates or well-meaning friends. Determine your needs and criteria first. Perform a gut-check: Are you ready to be in a relationship? Are you willing to invest the time to date? Do you know your non-negotiables when it comes to religion, children, politics, lifestyle, work and personal relationship goals?

Once you have been honest about these critical qualities, you are ready to begin your search. Here are some helpful resources to consider:

Online Dating
In some respects, the online experience is a positive one: You have daily access to meeting hundreds of individuals who might never have crossed your path otherwise. It has, however, become survival of the fittest.

Pros: A low barrier to entry. Light on the wallet, and you will experience an instant outcome. You have the opportunity to meet dozens of other singles. Consider specialized sites to narrow the field.

Cons: If you value privacy and honesty during the dating process; if you have limited time and are not looking for random dates, don’t want to meet a current employee or old math teacher, online dating is not for you.

Dating Services
Dating services offer more personalization than online services. They vary from quick lunches to speed dating to video matching.

Pros: You will have more control over your selection than you would with an online service. You can select a potential match upfront via video or a profile. Minimal to moderate cost.

Cons: Be prepared to sift through thousands of profiles and date someone whose background, stability, appropriateness, accuracy and sincerity are unverified. A dating service accepts enrollment from as many people as possible. It’s about filling a quota vs. receiving quality matches.

A matchmaker is an individual who chooses a mate for you. At first this may seem "old world," but a matchmaker is a highly effective and efficient process for entrepreneurs.

Pros: Time-saver for constrained, busy entrepreneurs. Discreet, highly personal, focused exclusively on you. A good matchmaker knows your individual preferences and personality. They will help you move outside your social or work circles, meeting individuals you might never have come across otherwise.

Cons: There are numerous "mom and pop" matchmakers who don’t have a clear process or who are in it because friends said they were good at fixing people up. Look for a professional who is accredited by the Better Business Bureau. Get extensive referrals.

The Personal Recruiter
Personal recruiting services are matchmakers who approach the process as an executive recruiter. They combine the same careful vetting processes used by recruiters to fill top level executive positions with the art of matchmaking.

Pros: A professional vetting process eliminates time wasted on inappropriate candidates. A highly targeted approach that delivers the ROI you’re looking for. You can be introduced to the love of your life with a minimal time investment.

Cons: This is typically a more costly approach. If you are looking to feel your way around the dating process or go on lots of dates, a personal recruiter is not for you. If you’re still planning to play the field, try online dating.

Regardless of the method, be strategic in your approach. Don’t settle. Dedicate time to finding the love of your life, if that’s what you want, because he or she is out there.


If you already have a serious partner, review the following questions to determine the health of your relationship. These questions not only help us learn what to look for, but they can serve as valuable tools allowing us to focus improvements on our existing relationships.

  • Do you feel safe and deeply cared for? Do you get the comfort and support you need, or is it missing in action, making you feel like holding back? Do you feel like a "sensitivity chip" is missing?
  • Is your partner plugged into your world? Does your partner care about your friends and family? Does he ask you about them or actively include them in your "couplehood?" Does she get upset that you spend time with them? Does your partner try to get out of going to family events or get-togethers with friends, leaving you to attend alone?
  • Can you be your real self with your partner? Can the not-so-nice side of you make an appearance and feel secure that your partner is still going to love you? Can you trust her with your fears, insecurities and vulnerabilities, or do you fear they will be used against you at a later date?
  • Does your partner honor what is important to you? Does she show how much she cares about your interests, goals and dreams?
  • Does your partner support and build your self-confidence? Do you feel he is in your corner, or do you feel he is critical and that you are not doing something right or not living up to his standards?
  • Will your partner do something for you even though he really doesn’t feel like doing it? Does he make sacrifices for you and not make a big deal out of it afterward? If you have a problem, does she genuinely listen, or does she offer advice and tell you how to fix it rather than trying to understand your issues?
  • When your partner is angry or there is a conflict, how does she treat you? Does he ignore you or belittle you? If someone were treating your friend, sister or child the way he treats you, would it be acceptable to you or would you tell your loved one to get out of the relationship because she deserves better?
  • Does your partner love you the way you want to be loved? When you state your wants, needs and desires — what is okay and not okay with you — does she acknowledge and do something positive about your requests?
  • Is your partner consistent in the way he loves you, even at times when you are inconsistent? Are his words and expressed feelings and actions consistent over time? Does she walk the talk, or does she have double standards for how she wants to be treated versus how she treats you or others?
  • If you broke up, would you miss your partner or the relationship? It’s great being a couple, but you need to separate the "together" things you do from the individual. Do you love her on her own, or do you love her as part of the two of you?

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