Tom’s First Year as a Financial Planner at Skylight


We recently caught up with Tom Dlugopolsky, winner of Skylight’s New Associate of the Year 2016, to get the lowdown on what his first year as a financial planner at Skylight has been like.

On the eve of completing your first year with Skylight, what have you enjoyed most about being a financial planner?

I particularly like that I get to help people.  It’s one thing to say that but it’s another thing to live it. 

I also love interacting with people.  In my previous job working in a factory environment, I mostly dealt with machines!  It’s more intricate and complicated working with people.  You need to figure out their pain points and then how to help them – this is a challenge I thrive on.

Any moments with clients that stand out for you where you’ve said to yourself “now I know why I became a financial planner”?

Yes, getting a hug from one of my clients!  I can even remember the date - June 15th 2016. I’d never had a hug before in my previous job so while I was initially a little taken aback, it was an amazing feeling to get that hug and feel her gratitude.

What would you say are the biggest challenges starting out as a financial planner and how did you overcome these?

I guess these have been the biggest challenges for me:

  • Facing up to the awkwardness of lifting the phone and making a “cold” call - I came to the realization that the phone was just a required tool to complete my job.  And the more I picked it up the easier it became
  • Finding enough people to reach out to – I started networking and spending multiple nights a week at different events to meet new people and create opportunities
  • Switching from a salary to a commission based income - I took the advice I give to my clients to create a healthy reserve and work hard enough that money flows on a regular basis
  • Initially perceiving myself as a “salesman” - I surrounded myself with; friends, family, clients, and coworkers that have a deep level of understanding for what it is to be a financial planner and having them (and more importantly me) realize that what I do truly does add a lot of value to people’s lives.
  • Getting the right work/life balance – I manage this by writing down what is truly important to me. And I calendar everything, from business meetings to Christmas with my family. My calendar runs my life

What’s it like to work for yourself?

I really like the freedom and flexibility of being a financial planner and being in control of, and accountable for, my schedule.  For example, I also coached high school girls’ volleyball so I was able to fit that in around my work.  Also, recently my grandma was sick and I was able to go visit her in hospital when I wanted. 

What is the culture like at Skylight?

It’s a fluid and fun place to work.  There’s no stringent guidelines and you have the freedom to grow and do what you want.  And there’s one of the best views of Cleveland from the Skylight penthouse!

What are the people at Skylight like to work with?

They are a great bunch.  There’s a wide variety of people, from partners and senior associates who are very experienced to others who are at the same stage of their career as me and who are of a similar age and mind-set - this makes life lots of fun and interesting! It’s good to be exposed to the different perspectives, learn from the different experiences and find out what each individual is good at.

Any advice for anyone starting a career as a financial planner?

I’d say run before you know how to walk.  If you try to structure everything and know everything you’ll fall behind.  I think experiential learning is the best way to learn.

What’s been your biggest achievement in your first year?

Being awarded Skylight’s New Associate of the Year.  That was awesome.  While it’s really rewarding to be able to help people it’s also great to get an award that’s for me.  It’s like getting the gold star!

What’s the most important lesson you have learnt in the last year?

To listen.  By that I mean, not just paying attention to the words but listening to the tone and being able to read behind the lines.

What’s the best advice you have received in your first year?

The best advice I’ve received was from Dan Brennan (who’s the Chief Operating Officer) who told me to talk to as many other financial planners as possible.  He advised me to go out for lunch/coffee and find out the secret to their success.

What’s the worst mistake you have made this year and what did you learn from this?

Thinking I could do this all by myself. When I first started, I knew I had an entrepreneurial spirit as I had experience of running a factory and I thought I knew everything.  It took me about three months to realize I couldn’t do it alone and that I had to accept help and embrace the team concept.  It was humbling to admit to myself that I wasn’t the smartest person in the world.  Now I know that being humble is the key to life.  I now put others first and people recognize this and appreciate it.

So overall, are you glad you chose to work for Skylight as a financial planner and has it met your expectations?

I am very satisfied with my choice of career.  I can honestly say that I didn’t expect that I would have to work so hard!  But I don’t mind this as I really enjoy the work and find it very fulfilling.


Thanks Tom for sharing with us!

To find out more about a career as a financial planner or to join our summer internship program Visit join our team or contact Rob Fichter, Head of Skylight's Recruitment Division at 614-790-9803.


Thomas Dlugopolsky is a registered representative of and offers securities, investment advisory and financial planning through MML Investors Services, LLC.  Member SIPC OSJ:2012 W. 25th Street, Suite 900, Cleveland OH 44113. 216-621-5680.  CRN201902-208137


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